Complexity of Chemical Graphs in Terms of Size, Branching, and Cyclicity

SAR and QSAR in Environmental Research
Vol. 17, No. 4, August 2006, 429–450
Complexity of chemical graphs in terms of size,

branching, and cyclicity
A. T. BALABAN*y, D. MILLSz, V. KODALIz and S. C. BASAKz
yTexas A&M University Galveston, 5007 Avenue U, Galveston, TX 77551, USA
zUniversity of Minnesota Duluth, Natural Resources Research Institute,
5013 Miller Trunk Highway, Duluth, MN 55811, USA
(Received 9 November 2005; in final form 1 June 2006)
Chemical graph complexity depends on many factors, but the main ones are size, branching,
and cyclicity. Some molecular descriptors embrace together all these three parameters, which
cannot then be disentangled. The topological index J (and its refinements that include
accounting for bond multiplicity and the presence of heteroatoms) was designed to compensate
in a significant measure for graph size and cyclicity, and therefore it contains information
mainly on branching. In order to separate these factors, two new indices (F and G) related with
J are proposed, which allow to group together graphs with the same size into families of
constitutional formulas differing in their branching and cyclicity. A comparison with other
topological indices revealed that a few other topological indices vary similarly with index G,
notably DN2S(4) among the triplet indices, and TOTOP among the indices contained in the
Molconn-Z program. This comparison involved all possible chemical graphs (i.e. connected
planar graphs with vertex degrees not higher than four) with four through six vertices, and
all possible alkanes with four through nine carbon atoms.
Keywords: Complexity; Graph size; Branching; Cyclicity; Centricity; New topological indices
1. Introduction
Complexity is a fuzzy notion that has recently begun to be treated scientifically by

listing and analyzing the factors that influence it [1–5]. Since this notion applies to many
important day-to-day activities, a mathematical treatment can shed light on some
aspects of complexity.
The present paper deals with molecular graphs, which are usually hydrogen-depleted
constitutional formulas of organic compounds. A graph G ¼ G(V, E) is a non-empty set
of elements v called vertices and of elements e called edges, which are unordered pairs
of vertices. In chemical graphs, vertices symbolize non-hydrogen atoms, and edges
*Corresponding author. Email: balabana@tamug.edu
SAR and QSAR in Environmental Research

ISSN 1062-936X print/ISSN 1029-046X online ß 2006 Taylor & Francis
DOI: 10.1080/10629360600884421
430 A. T. Balaban et al.
symbolize covalent bonds. When other atoms than carbon appear in the formulas (such
atoms are called heteroatoms), one has a ‘‘colored graph’’, with vertices of different
types (colors), and when multiple bonds exist in the chain, the graph is called a
‘‘multigraph’’. Sometimes a vertex may be connected to itself by a loop, and in this case
we have a ‘‘general graph’’ [6, 7]. The order of the hydrogen-depleted graph is the
number N of non-hydrogen atoms; in the following, N will be called the ‘‘size’’ of the
graph. In the present paper we shall adopt a restrictive use of the term ‘‘chemical
graph’’: a connected planar graph devoid of loops or multiple edges, with vertex degrees
not higher than four.
Sixty years ago, for correlating physical-chemical properties of chemical compounds,
Wiener [8] devised a simple method for converting structural formulas, which are
discrete objects without evident metric properties, into numbers that can then be
introduced into mathematical formulas for quantitative structure-property relation-
ships (QSPRs), soon to be followed by quantitative structure-activity relationships
(QSARs) for biologically-active compounds. This was the beginning of a trend that
continues to this day, namely to devise topological indices (TIs, a name introduced by
Hosoya [9]) for QSAR and QSPR [10–12].
The first-generation TIs, namely Wiener’s index W [8], Hosoya’s index Z [9], the
Zagreb indices [13], the centric indices [14], and a few other TIs, are integer numbers
derived from integer ‘‘local vertex invariants (LOVIs)’’ assigned for each vertex i, such
as vertex degrees Vi (sums of entries aij ¼ aji in rows or columns of the graph adjacency
matrix A, with entry 1 for adjacent vertices i and j, and 0 otherwise) or distance sums Si
(sums of entries in rows or columns of the graph distance matrix D, with the same entry
1 for adjacent vertices and 0 on the main diagonal as in the preceding case, but higher
entries for all other matrix elements, indicating the topological distance). The
topological distance dij ¼ dji is the number of edges on the shortest path between
vertices i and j. Such 1st generation indices have the drawback that they have high
degeneracy, i.e. low discriminating ability, with many non-isomorphic graphs having
the same value for the index.
The TIs that are most frequently used till now belong to the second generation, and
they are real numbers based on integer LOVIs such as Vi or Si. The Randić molecular
connectivity [15], the related Kier-Hall indices m and mv [16, 17], the mean square
distance [18], as well as the Balaban indices J [19] and Jhet [20, 21] are such second
generation indices. Other second generation indices such as the overall connectivity
index have been published by Bonchev [22]. Several types of inverse/reverse Wiener
indices have been described [23], and one of them (introduced independently in Zagreb
[24] and in Bucharest [25]) has been called the Harary index, honoring the recently
departed eminent graph theorist who made substantial contributions to the chemical
graph theory [26].
More recently, third-generation indices have been introduced. They are real numbers
based on real-number LOVIs. Examples are information-theoretic indices [27–31]
and the triplet indices [32]. These triplet indices convert a matrix into a system of linear
equations whose solutions are LOVIs, by including a column vector on the
main diagonal and another column vector as the free term. These column vectors
may convey chemical information (e.g., the atomic number Z of the atom symbolized
by the corresponding vertex), graph-theoretical information (e.g., the vertex degree V or
the distance sum S of the corresponding vertex), or simply a constant numerical data
(e.g., number 1, or the number N of vertices in the graph, or its square, N2). Then the
Complexity of chemical graphs 431
LOVIs xi are converted into a molecular descriptor by one of the following four
operators:
P
1. Summation: i xi P
2. Summation of squares: i x2iP
3. Summation of square roots: i x1=2
i P
4. Summation of reciprocal square roots of cross-products over edges ij: ij(xixj)1/2
The notation for the triplet indices contains three letters denoting the matrix and
the two column vectors, followed by the number of the above operator in brackets.
A special computer program (TRIPLET) was developed at the Natural Resources
Research Institute, University of Minnesota–Duluth for these indices. With the help of
the programs TRIPLET, POLLY v2.3, and Molconn-Z v3.5, the values and clustering
of numerous TIs were analyzed for various hydrocarbons and for data bases with
diverse chemicals [33, 34] Representative for the first (largest) cluster was the triplet
index DN2Z(4) [33, 34]. This index is similar to other triplet indices DN2Y(4), such as
DN2S(4), where the free-term vector Y (in this case the distance sum) is appreciably
smaller than the main-diagonal vector N2.
2. On cyclicity and centricity
Even the simplest TIs (such as the Wiener index) vary with the number and size of rings
(cyclicity), as well as the centricity of branches and with the degree of branching. The
‘‘overall topological shape’’ for acyclic graphs has as branching extremes the linear
chain with zero branches and the ‘‘star graph’’ with N 1 branches connected to a
central vertex. For acyclic chemical graphs (corresponding to alkanes), the latter
extreme must be replaced with other structures having vertex degrees not higher
than four.
Branching for alkanes depends not only on the number of branches, but also on the
position of branches along the longest acyclic chain. According to the IUPAC
nomenclature rules, the names of most organic compounds are derived from the name
of the parent hydrocarbon. In turn, acyclic compounds have names that are derived
from the longest acyclic chain, defined according to a sequence of rules. One can
enumerate all alkanes according to the number N of vertices in the hydrogen-depleted
graph and the number of atoms in the longest acyclic chain [35]. Usually branches closer
to the center lead to a more compact shape of the graph, and to lower average distances.
One component of cyclicity is defined by the cyclomatic number, which will be
denoted here by R (the conventional number of rings in a graph with N vertices and
E edges, equal to the minimal number of edges that must be deleted in order to obtain
an acyclic graph):
R¼ENþ1 ð1Þ
Of course, even in the simplest condensed or bridged bi- or polycyclic graph, one
may discern more than R rings, for instance in the pentacyclic cubane molecule one
sees six 4-membered rings and many 6- and 8-membered rings. The problem of
finding the smallest set of R smallest rings in polycyclic graphs has been solved
algorithmically [36–50].
Centricity is easily defined for acyclic graphs, which have a unique center that is either
one vertex or a pair of adjacent vertices (depending on whether the longest chain has an
odd or an even number of vertices). However, for cyclic graphs, the problem of defining
centric vertices is more complicated, and only a few selected bibliographic references
will be indicated [51–57].
3. Molecular descriptors that separate size, cyclicity, and branching
The index J is the distance-based average connectivity [18–21]. It is related to the

Randić index, using the above operator numbered as four (summation of reciprocal
square roots of products over each edge, also known as the Ivanciuc–Balaban operator)
[58–60], but using as LOVIs distance sums (instead of vertex degrees as required for the
Randić index ), and averaging for the numbers E of edges and R of cycles:
X
E
J¼ ðSi Sj Þ1=2 ð2Þ
ðR þ 1Þ ij
This index was designed so as not to increase automatically with graph size,
branching, and cyclicity, like most other indices (W, Z, , m, etc). It was shown recently
that J has a parallel variation with W [61, 62] but has a much higher discrimination
ability (for alkanes the first degeneracy appears at N ¼ 7 for W, at N ¼ 8 for , and at
N ¼ 12 for J) [63]. It was repeatedly mentioned that index J (which for an infinite linear
chain symbolizing polyethylene has the asymptotic value [64] of ¼ 3.14159, and for
polypropylene the value 3/2) is not to be used alone in uniparametric correlations in
QSPR studies for properties that increase with the graph size, yet several authors did
publish such nonsensical uniparametric studies, arguing that J is not fit for QSAR
studies. On the contrary, index J has many ‘‘desirable’’ features (facile accommodation
of bond multiplicity and presence of heteroatoms). Even its asymptotical limitations are
useful in correlations with polymer properties [65]. Interestingly, TIs of alkanes lead
to almost converging distinct lines in a diagram with W1 versus J [66].
Along with branching, centricity and complexity, cyclicity [55, 57] is also a fuzzy
concept. One can consider cyclicity to be measurable via the cyclomatic number R.
However, as seen in figures 1 and 2, there are four possibilities for bicyclic systems (with
isolated, spiranic, condensed, and bridged rings), and even more possibilities for
polycyclic ones, so that even for the same number R of rings, there is still considerable
variation, similarly to the situation for the number and position of branches (reflected
in vertex degrees and in branch centricity). Vertex degrees have been limited to be
at most four in figures 1 and 2. On excluding the non-planar graphs 27, 83 and 92 one
obtains chemical graphs representing constitutional isomers. Stereoisomerism (diaster-
eomerism and enantiomerism) should also be considered but it has been omitted in
figures 1 and 2.
We are introducing in this paper two new indices. The first is denoted by F:
X
F¼E ðSi Sj Þ1=2 ¼ ðR þ 1ÞJ ð3Þ
ij
and it has the interesting property that it allows the separation of graph size, cyclicity,
and branching. Table 1 shows data for all possible cyclic and acyclic chemical graphs
4-Vertexgraphs 5-Vertexgraphs
Acyclic
1 2 7 8 9
Monocyclic
3 4
10 11 12 13 14
Bicyclic
5
15 16 17 18 19
Tricyclic
6 20 21 22 23
Tetracyclic
24 25
Pentacyclic
26
Hexacyclic
27
Figure 1. All possible graphs with four and five vertices; on excluding the non-planar graph 27 (K5), one has
all possible chemical graphs.
(whose upper limit for vertex degree is four) with four through six vertices (indicated
with corresponding numbers in figures 1 and 2), and table 2 presents data for all alkanes
with seven through nine vertices. These tables also contain for comparison the values of
other molecular descriptors: the Wiener (W) index, one of the triplet indices, DN2S(4),
and Kier-Hall’s index TOTOP (TOtal TOPological index). The last index is one of
the Molconn-Z indices [67, 68]. Index F has the interesting property that it allows the
separation of graph size, cyclicity, and branching.
A more appropriate index (denoted by G) for graph complexity is derived from J
and F:
X
N2 JðR þ 1Þ N2 F N2 E
G¼ ¼ ¼ ðSi Sj Þ1=2 ð4Þ
ðN þ R þ 1Þ ðN þ R þ 1Þ ðN þ R þ 1Þ ij
Acyclic
28 29 30 31 32
33 34 35 36 37 38 Monocyclic
39 40 41 42 43 44
45 47 48 50 Bicyclic
46 49
51 52 53 54 55 56 57 58 59
60 61 62 63 65 66 Tricyclic
64
67 68 69 70 71 72
Tetracyclic
73 74 75 76 77 78 79 80 81 82 83
Pentacyclic
84 85 86 87 88 89 90
Hexacyclic
91 92
Heptacyclic
93
Figure 2. All possible acyclic and cyclic chemical graphs with six vertices.
Table 1. Alkanes C7–C9 and their topological indices: W and J.
No. SMILES Code Alkane name Abbreviated name W J
1 CCCCCCC Heptane C7 56 2.4475

2 CC(C)CCCC 2-Methylhexane 2-M-C6 52 2.6783
3 CCC(C)CCC 3-Methylhexane 3-M-C6 50 2.8318
4 CC(C)CC(C)C 2,4-Dimethylpentane 2,4-MM-C5 48 2.9532
5 CCC(C(C))CC 3-Ethylpentane 3-E-C5 48 2.9923
6 CC(C)C(C)CC 2,3-Dimethylpentane 2,3-MM-C5 46 3.1442
7 CC(C)(C)CCC 2,2-Dimethylpentane 2,2-MM-C5 46 3.1545
8 CCC(C)(C)CC 3,3-Dimethylpentane 3,3-MM-C5 44 3.3604
9 CC(C)(C)C(C)C 2,2,3-Trimethylbutane 2,2,3-MMM-C4 42 3.5412
10 CCCCCCCC Octane C8 84 2.5301
11 CC(C)CCCCC 2-Methylheptane 2-M-C7 79 2.7158
12 CCC(C)CCCC 3-Methylheptane 3-M-C7 76 2.8621
13 CCCC(C)CCC 4-Methylheptane 4-M-C7 75 2.9196
14 CC(C)CCC(C)C 2,5-Dimethylhexane 2,5-MM-C6 74 2.9278
15 CCC(C(C))CCC 3-Ethylhexane 3-E-C6 72 3.0744
16 CC(C)CC(C)CC 2,4-Dimethylhexane 2,4-MM-C6 71 3.0988
17 CC(C)(C)CCCC 2,2-Dimethylhexane 2,2-MM-C6 71 3.1118
18 CC(C)C(C)CCC 2,3-Dimethylhexane 2,3-MM-C6 70 3.1708
19 CCC(C)C(C)CC 3,4-Dimethylhexane 3,4-MM-C6 68 3.2925
20 CC(C)C(C(C))CC 3-Ethyl-2-methylpentane 3-E-2M-C5 67 3.3549
21 CCC(C)(C)CCC 3,3-Dimethylhexane 3,3-MM-C6 67 3.3734
22 CC(C)(C)CC(C)C 2,2,4-Trimethylpentane 2,2,4-C5 66 3.3889
23 CC(C)C(C)C(C)C 2,3,4-Trimethylpentane 2,3,4-C5 65 3.4642
24 CCC(C(C))(C)CC 3-Ethyl-3-methylpentane 3-E3M-C5 64 3.5832
25 CCC(C)C(C)(C)C 2,2,3-Trimethylpentane 2,2,3-MMM-C5 63 3.6233
26 CC(C)C(C)(C)CC 2,3,3-Trimethylpentane 2,3,3-MMM-C5 62 3.7083
27 CC(C)(C)C(C)(C)C 2,2,3,3-Tetramethylbutane 2,2,3,3-MMMM-C4 58 4.0204
28 CCCCCCCCC Nonane C9 120 2.5951
29 CC(C)CCCCCC 2-Methyloctane 2-M-C8 114 2.7467
30 CCC(C)CCCCC 3-Methyloctane 3-M-C8 110 2.8766
31 CC(C)CCCC(C)C 2,6-Dimethylheptane 2,6-MM-C7 108 2.9147
32 CCCC(C)CCCC 4-Methyloctane 4-M-C8 108 2.9548
33 CCC(C)CCC(C)C 2,5-Dimethylheptane 2,5-MM-C7 104 3.0608
34 CC(C)(C)CCCCC 2,2-Dimethylheptane 2,2-MM-C7 104 3.0730
35 CCC(CC)CCCC 3-Ethylheptane 3-E-C7 104 3.0923
36 CC(C)CC(C)CCC 2,4-Dimethylheptane 2,4-MM-C7 102 3.1513
37 CC(C)C(C)CCCC 2,3-Dimethylheptane 2,3-MM-C7 102 3.1553
38 CCCC(CC)CCC 4-Ethylheptane 4-E-C7 102 3.1753
39 CCC(C)CC(C)CC 3,5-Dimethylheptane 3,5-MM-C7 100 3.2231
40 CC(C)CCC(C)(C)C 2,2,5-Trimethylhexane 2,2,5-MMM-C6 98 3.2807
41 CC(C)CC(CC)CC 4-Ethyl-2-methylhexane 4-E-2-M-C6 98 3.3074
42 CCC(C)C(C)CCC 3,4-Dimethylheptane 3,4-MM-C7 98 3.3248
43 CCC(C)(C)CCCC 3,3-Dimethylheptane 3,3-MM-C7 98 3.3301
44 CC(C)C(C)CC(C)C 2,3,5-Trimethylhexane 2,3,5-MMM-C6 96 3.3766
45 CC(C)C(CC)CCC 3-Ethyl-2-methylhexane 3-E2-M-C6 96 3.4101
46 CCCC(C)(C)CCC 4,4-Dimethylheptane 4,4-MM-C7 96 3.4311
47 CCC(C)CC(C)(C)C 2,2,4-Trimethylhexane 2,2,4-MMM-C6 94 3.4673
48 CCC(CC)C(C)CC 3-Ethyl-4-methylhexane 3-E4-M-C6 94 3.4995
49 CC(C)C(C)C(C)CC 2,3,4-Trimethylhexane 2,3,4-MMM-C6 92 3.5758
50 CCC(C)(C)CC(C)C 2,4,4-Trimethylhexane 2,4,4-MMM-C6 92 3.5768
51 CC(C)(C)C(C)CCC 2,2,3-Trimethylhexane 2,2,3-MMM-C6 92 3.5887
52 CCC(CC)(C)CCC 3-Ethyl-3-methylhexane 3-E3-M-C6 92 3.6174
53 CC(C)C(CC)C(C)C 3-Ethyl-2,4-dimethylpentane 3,E2,4-MM-C5 90 3.6776
54 CC(C)C(C)(C)CCC 2,3,3-Trimethylhexane 2,3,3-MMM-C6 90 3.7021
55 CC(C)(C)CC(C)(C)C 2,2,4,4-Tetramethylpentane 2,2,4,4-MMMM-C5 88 3.7464
56 CC(C)(C)C(C(C))CC 3-Ethyl-2,2-dimethylpentane 3-E2,2-MM-C5 88 3.7929
57 CCC(C)(C)C(C)CC 3,3,4-Trimethylhexane 3,3,4-MMM-C6 88 3.8024
58 CCC(CC)(CC)CC 3,3-Diethylpentane 3,3-EE-C5 88 3.8247
59 CC(C)(C)C(C)C(C)C 2,2,3,4-Tetramethylpentane 2,2,3,4-MMMM-C5 86 3.8776
60 CC(C)C(CC)(C)CC 3-Ethyl-2,3-dimethylpentane 3-E2,3-MM-C5 86 3.9192
61 CC(C)C(C)(C)C(C)C 2,3,3,4-Tetramethylpentane 2,3,3,4-MMMM-C5 84 4.0137
62 CCC(C)(C)C(C)(C)C 2,2,3,3-Tetramethylpentane 2,2,3,3-MMMM-C5 82 4.1447
Table 2. Graphs with 4–6 vertices (Nos. as in figures 1 and 2), and alkanes with 7–9 carbon atoms (Nos. as
in table 1) with some of their TIs.
No. N R W J F G DN2S(4) TOTOP
1 4 0 10 1.97474 1.9747 6.3192 14.1059 7.6483

2 4 0 9 2.32379 2.3238 7.4361 16.1558 7.7798
3 4 1 8 2.00000 4.0000 10.6667 20.0000 11.3889
4 4 1 8 2.17110 4.3422 11.5792 22.0154 11.5574
5 4 2 7 2.48006 7.4402 17.0061 29.1852 16.3740
6 4 3 6 3.00000 12.0000 24.0000 38.0000 22.7500
7 5 0 20 2.19061 2.1906 9.1275 18.4550 10.5529
8 5 0 18 2.53954 2.5395 10.5814 20.8191 10.7935
9 5 0 16 3.02372 3.0237 12.5988 24.0703 11.0583
14 5 1 17 1.99894 3.9979 14.2781 25.8889 14.8249
11 5 1 16 2.07967 4.1593 14.8548 26.3617 14.9840
10 5 1 15 2.08333 4.1667 14.8809 25.8333 14.6361
13 5 1 16 2.20344 4.4069 15.7389 28.1868 15.2749
12 5 1 15 2.38220 4.7644 17.0157 29.9076 15.3194
19 5 2 14 2.19089 6.5727 20.5396 33.5543 20.4757
17 5 2 15 2.19235 6.5771 20.5533 34.5543 20.7402
15 5 2 14 2.19393 6.5818 20.5681 33.6749 20.3330
18 5 2 14 2.29966 6.8990 21.5593 35.4242 20.1850
16 5 2 14 2.37197 7.1159 22.2372 36.6997 20.8751
21 5 3 13 2.38901 9.5560 26.5446 41.3296 27.8046
20 5 3 13 2.48607 9.9443 27.6230 43.1674 27.7246
22 5 3 13 2.55465 10.2186 28.3850 44.6455 28.3617
23 5 3 13 2.58080 10.3232 28.6756 44.8983 27.9127
25 5 4 12 2.71108 13.5554 33.8885 50.5935 37.5699
24 5 4 12 2.80428 14.0214 35.0535 52.5397 37.5013
26 5 5 11 3.13746 18.8248 42.7836 61.6442 50.5133
27 5 6 10 3.57143 25.0000 52.0834 72.5000 67.9333
28 6 0 35 2.33909 2.3391 12.0296 22.7762 13.5229
29 6 0 32 2.62721 2.6272 13.5114 24.9765 13.8072
30 6 0 31 2.75418 2.7542 14.1644 26.0121 13.9209
32 6 0 29 2.99350 2.9935 15.3951 27.7239 14.1600
31 6 0 28 3.16849 3.1685 16.2951 29.1928 14.2940
37 6 1 31 1.87629 3.7526 16.8866 29.5089 17.9935
44 6 1 27 2.00000 4.0000 18.0000 30.0000 17.8967
39 6 1 29 2.01427 4.0285 18.1284 31.1401 18.3798
36 6 1 29 2.09391 4.1878 18.8452 32.5498 18.7327
41 6 1 28 2.11237 4.2247 19.0113 32.3816 18.8118
38 6 1 28 2.12947 4.2589 19.1652 32.5627 18.4576
43 6 1 26 2.18411 4.3682 19.6570 32.7274 18.3709
42 6 1 27 2.20160 4.4032 19.8144 33.3904 18.8868
35 6 1 27 2.27633 4.5527 20.4870 34.7133 18.8261
33 6 1 27 2.31136 4.6227 20.8022 35.2972 19.3473
40 6 1 26 2.31144 4.6229 20.8030 34.7499 18.9563
34 6 1 26 2.41329 4.8266 21.7196 36.4853 19.3796
58 6 2 27 1.91555 5.7467 22.9866 37.2367 23.1224
56 6 2 25 2.02774 6.0832 24.3329 38.6988 24.4098
54 6 2 27 2.05684 6.1705 24.6821 40.5480 25.5128
53 6 2 25 2.08348 6.2504 25.0018 39.9486 24.8038
57 6 2 24 2.09486 6.2846 25.1383 39.6348 24.1433
48 6 2 26 2.09674 6.2902 25.1609 40.8630 24.8244
50 6 2 25 2.10846 6.3254 25.3015 40.4219 25.1267
52 6 2 25 2.11311 6.3393 25.3573 40.5992 24.9804
59 6 2 23 2.16250 6.4875 25.9500 40.5017 24.4216
45 6 2 25 2.16885 6.5066 26.0262 41.7369 24.6937
49 6 2 24 2.18660 6.5598 26.2392 41.4877 25.1973
(continued )
Table 2. Continued.
55 6 2 25 2.21365 6.6410 26.5638 42.6333 25.5267

51 6 2 24 2.21561 6.6468 26.5873 42.1259 25.0949
46 6 2 25 2.23205 6.6962 26.7846 43.0922 25.6927
47 6 2 24 2.33850 7.0155 28.0620 44.7041 25.8562
69 6 3 25 2.10882 8.4353 30.3670 47.7416 32.9955
60 6 3 24 2.11839 8.4736 30.5048 47.1063 33.4292
72 6 3 24 2.14757 8.5903 30.9250 47.6939 31.7615
67 6 3 23 2.15076 8.6030 30.9709 47.1260 32.0230
63 6 3 24 2.19465 8.7786 31.6030 48.9894 33.4298
65 6 3 23 2.20342 8.8137 31.7293 48.4311 32.6363
61 6 3 23 2.23432 8.9373 32.1742 49.1960 33.7274
62 6 3 23 2.25940 9.0376 32.5354 49.8140 33.8637
71 6 3 22 2.26213 9.0485 32.5747 49.1280 32.8565
66 6 3 22 2.26361 9.0544 32.5960 49.2019 32.6079
70 6 3 24 2.26713 9.0685 32.6467 50.7033 33.7138
64 6 3 23 2.31024 9.2410 33.2675 51.0257 33.6905
68 6 3 23 2.36987 9.4795 34.1261 52.5936 34.6649
79 6 4 21 2.31429 11.5715 37.8702 55.2857 43.9150
83 6 4 21 2.31429 11.5715 37.8702 55.2857 44.8200
76 6 4 23 2.32485 11.6243 38.0430 57.3665 44.7471
78 6 4 22 2.35444 11.7722 38.5272 57.1345 43.3907
80 6 4 22 2.35444 11.7722 38.5272 57.1379 44.1504
81 6 4 21 2.36215 11.8108 38.6534 56.5361 43.5482
82 6 4 21 2.36215 11.8108 38.6534 56.5395 44.2340
75 6 4 21 2.36348 11.8174 38.6751 56.6179 43.9596
74 6 4 22 2.38424 11.9212 39.0148 58.0161 45.2681
73 6 4 21 2.41274 12.0637 39.4812 57.9582 43.6837
77 6 4 22 2.45552 12.2776 40.1812 59.9545 45.2919
86 6 5 20 2.53357 15.2014 45.6043 64.9006 58.8921
87 6 5 20 2.53510 15.2106 45.6318 64.9938 59.2923
89 6 5 21 2.57389 15.4433 46.3300 67.1091 58.9584
88 6 5 20 2.57971 15.4783 46.4348 66.2284 59.6000
85 6 5 20 2.58124 15.4874 46.4623 66.3148 59.0493
90 6 5 20 2.58247 15.4948 46.4845 66.4031 59.2650
84 6 5 21 2.60352 15.6211 46.8634 68.1292 60.7030
91 6 6 19 2.76438 19.3507 53.5864 74.5658 80.2752
92 6 6 19 2.76583 19.3608 53.6146 74.6657 80.5395
93 6 7 18 3.00000 24.0000 61.7143 84.0000 109.3733
1 7 0 56 2.44747 2.4475 14.9908 27.0827 16.5385
2 7 0 52 2.67826 2.6783 16.4043 29.0301 16.846
3 7 0 50 2.83182 2.8318 17.3449 30.4562 17.0048
4 7 0 48 2.95322 2.9532 18.0885 31.2886 17.1763
5 7 0 48 2.9923 2.9923 18.3278 31.8548 17.1618
6 7 0 46 3.14421 3.1442 19.2583 33.0705 17.4067
7 7 0 46 3.15449 3.1545 19.3213 33.2603 17.4218
8 7 0 44 3.36044 3.3604 20.5827 35.0656 17.6511
9 7 0 42 3.54120 3.5412 21.6899 36.4332 17.8913
10 8 0 84 2.53006 2.5301 17.9915 31.3804 19.588
11 8 0 79 2.71584 2.7158 19.3126 33.0884 19.9096
12 8 0 76 2.86207 2.8621 20.3525 34.5993 20.0921
13 8 0 75 2.91961 2.9196 20.7617 35.2215 20.1372
14 8 0 74 2.92782 2.9278 20.8201 34.9776 20.2416
15 8 0 72 3.07437 3.0744 21.8622 36.6926 20.316
16 8 0 71 3.09883 3.0988 22.0361 36.7279 20.4478
17 8 0 71 3.11177 3.1118 22.1281 37.0142 20.5323
18 8 0 70 3.17082 3.1708 22.5481 37.5565 20.5646
(continued )
Table 2. Continued.
19 8 0 68 3.29248 3.2925 23.4132 38.7162 20.7289

20 8 0 67 3.35488 3.3549 23.8569 39.2915 20.767
21 8 0 67 3.37338 3.3734 23.9885 39.6316 20.8528
22 8 0 66 3.38892 3.3889 24.099 39.4498 20.9107
23 8 0 65 3.46423 3.4642 24.6345 40.2085 21.0178
24 8 0 64 3.58321 3.5832 25.4806 41.6165 21.1295
25 8 0 63 3.62328 3.6233 25.7656 41.8433 21.2626
26 8 0 62 3.70832 3.7083 26.3703 42.6852 21.3756
27 8 0 58 4.02039 4.0204 28.5894 45.5149 21.8632
28 9 0 120 2.59508 2.5951 21.0202 35.6724 22.6638
29 9 0 114 2.74669 2.7467 22.2482 37.1759 22.9946
30 9 0 110 2.87662 2.8766 23.3006 38.644 23.1914
31 9 0 108 2.91466 2.9147 23.6088 38.7891 23.3311
32 9 0 108 2.95482 2.9548 23.934 39.5842 23.2603
33 9 0 104 3.06082 3.0608 24.7926 40.4139 23.5386
34 9 0 104 3.07299 3.073 24.8912 40.7256 23.6457
35 9 0 104 3.09225 3.0923 25.0472 41.0104 23.4518
36 9 0 102 3.15125 3.1513 25.5251 41.519 23.6311
37 9 0 102 3.15528 3.1553 25.5578 41.6323 23.7028
38 9 0 102 3.17534 3.1753 25.7203 41.9303 23.5187
39 9 0 100 3.22305 3.2231 26.1067 42.2205 23.7708
40 9 0 98 3.28071 3.2807 26.5738 42.6734 24.0034
41 9 0 98 3.30739 3.3074 26.7899 43.1125 23.8329
42 9 0 98 3.32476 3.3248 26.9306 43.4692 23.9383
43 9 0 98 3.33007 3.3301 26.9736 43.6081 24.014
44 9 0 96 3.3766 3.3766 27.3505 43.752 24.0853
45 9 0 96 3.41009 3.4101 27.6217 44.3391 23.9951
46 9 0 96 3.43105 3.4311 27.7915 44.7453 24.1051
47 9 0 94 3.46726 3.4673 28.0848 44.7294 24.2593
48 9 0 94 3.49948 3.4995 28.3458 45.2576 24.1648
49 9 0 92 3.57583 3.5758 28.9642 45.9587 24.4195
50 9 0 92 3.57675 3.5768 28.9717 45.9761 24.4196
51 9 0 92 3.58873 3.5887 29.0687 46.2421 24.4976
52 9 0 92 3.61739 3.6174 29.3009 46.6711 24.4052
53 9 0 90 3.67762 3.6776 29.7887 47.0194 24.4974
54 9 0 90 3.70209 3.7021 29.9869 47.494 24.6551
55 9 0 88 3.74642 3.7464 30.346 47.5305 24.7705
56 9 0 88 3.79291 3.7929 30.7226 48.3109 24.7476
57 9 0 88 3.8024 3.8024 30.7994 48.4815 24.8266
58 9 0 88 3.82468 3.8247 30.9799 48.8002 24.7293
59 9 0 86 3.8776 3.8776 31.4086 49.0421 25.0046
60 9 0 86 3.91921 3.9192 31.7456 49.7047 24.9813
61 9 0 84 4.01374 4.0137 32.5113 50.5703 25.2335
62 9 0 82 4.14473 4.1447 33.5723 51.9849 25.4803
has the same degeneracy as J. One may see in figures 3 and 4 that F, G, DN2S(4), and
TOTOP are intercorrelated. A detailed discussion will follow in a subsequent
paragraph.
It is not difficult to understand the reason for the quasi-linear correlation between
indices F, G, and DN2S(4). We illustrate this reason by examining, for all constitutional
isomers of hexane and heptane, the LOVIs on which the topological index DN2S(4) is
based (table 3 and figure 5). For comparison we list also another set of LOVIs, namely
DN2N2, in which the free-term vector (N2) is larger than the free-term vector S. One
finds that the LOVIs DN2S and DN2N2 show a high intercorrelation, albeit in an
inverse relationship:
DN2 S 1 DN2 N2 ð5Þ
Indices F, G, and DN2S(4) result by applying operator (4) to the corresponding
LOVIs, namely the distance sum Si for F and G, and the LOVI values for DN2S – for
instance the values from table 3 for hexane and heptane isomers.
Table 3. LOVIs for non-equivalent carbons in hexane and heptane isomers.
Alkane DN2N2 DN2S S Smiles notation
C6 0.818 0.182 9 CCCCCC

0.772 0.228 11
0.684 0.316 15
2-M-C5 0.746 0.259 12 CC(C)CCC
0.834 0.166 8
0.833 0.167 8
0.787 0.213 10
0.697 0.303 14
3-M-C5 0.719 0.281 13 CCC(C)CC
0.809 0.191 9
0.854 0.146 7
0.766 0.233 11
2,3-MM-C5 0.849 0.150 7 CC(C)C(C)C
0.760 0.240 11
2,2-MM-C4 0.733 0.267 12 CC(C)(C)CC
0.825 0.174 8
0.871 0.129 6
0.782 0.218 10
C7 0.676 0.324 21 CCCCCCC
0.756 0.244 16
0.806 0.194 13
0.823 0.177 12
2-M-C6 0.817 0.184 12 CC(C)CCCC
0.737 0.263 17
0.833 0.167 11
0.816 0.184 12
0.765 0.235 15
0.683 0.317 20
3-M-C6 0.716 0.284 18 CCC(C)CCC
0.798 0.202 13
0.847 0.153 10
0.768 0.232 15
0.830 0.169 11
0.780 0.220 14
0.697 0.303 19
2,3-MM-C5 0.842 0.158 10 CC(C)C(C)CC
0.76 0.240 15
0.859 0.142 9
0.778 0.222 14
0.808 0.192 12
0.725 0.275 17
(continued )
Table 3. Continued.
Alkane DN2N2 DN2S S Smiles notation
2,4-MM-C5 0.827 0.173 11 CC(C)CC(C)C

0.746 0.254 16
0.844 0.156 10
3-E-C5 0.730 0.270 17 CCC(CC)CC
0.812 0.188 12
0.861 0.139 9
2,2-MM-C5 0.860 0.145 9 CC(C)(C)CCC
0.779 0.229 14
0.842 0.158 10
0.790 0.222 13
0.706 0.294 18
3,3-MM-C5 0.740 0.260 16 CCC(C)(C)CC
0.824 0.176 11
0.874 0.126 8
0.792 0.208 13
2,2,3-MMM-C5 0.871 0.129 8 CC(C)(C)C(C)C
0.789 0.211 13
0.854 0.145 9
0.770 0.229 14
4. Influence of structure on the TIs discussed here
We presented in figure 4, for alkanes with seven through nine carbon atoms, the
pairwise variation of indices J ¼ F, G, DN2S(4), and TOTOP. In figure 3 the same
variation is presented for the set of all graphs with four through six vertices, but in this
case J and F are equal only for alkanes (whose cyclomatic number R is zero).
Looking at table 2 first at index F, one observes that its value increases slightly with
the size and degree of branching of alkanes, but increases markedly with cyclicity.
Indeed, whereas the value of J of alkanes with four through nine carbon atoms lies
between two and four, index F becomes about (R þ 1) times larger for a polycyclic
system. There is little correlation between index J and indices DN2S(4) or TOTOP
for all graphs with four to six carbon atoms because J varies practically only with
branching, whereas the two latter indices vary with branching, size, and cyclicity.
However, in correlations between indices DN2S(4) or TOTOP versus index F, the
contribution of size appears separated in three curves for the three sizes of graphs with
four to six carbons or alkanes with seven to nine carbons. In the plot with DN2S(4)
versus F for all graphs with four to six vertices (figure 3) there are fairly well separated
regions with the same numbers of rings and graph vertices (with incipient overlap for
smaller numbers of rings and larger numbers of vertices), but on looking at the same
diagram for alkanes with seven to nine carbon atoms (figure 4), one can see that for
these acyclic graphs all points fall on quasi-parallel lines. In the corresponding diagrams
for TOTOP versus F, the same quasi-parallelism can be observed for alkanes, but for all
systems with four to six vertices the overlap is more pronounced. This clustering
according to the number of vertices and rings may be pushed further if need arises.
The three separate curves for alkanes with seven to nine carbons remain distinct in
the correlation between TOTOP versus G (figure 4). One should note that TOTOP
DN2S(4) vs J for all C4-C6 DN2S(4) vs G for all C4-C6

90 100
80 90
80
70
70
60 60
DN2S(4)
DN2S(4)
50 50
40 40
30
30
20
20 10
10 0
1.5 2.5 3.5 4.5 0 20 40 60 80
J G
DN2S(4) vs F for all C4-C6 TOTOP vs F for all C4-C6

90 30
80 25
70
20
60
TOTOP
DN2S(4)
50 15
40 10
30
5
20
10 0
0 10 20 30 0 20 40 60 80 100 120
F F
TOTOP vs G for all C4-C6 TOTOP vs J for all C4-C6
120 120
100 100
80 80
TOTOP
TOTOP
60 60
40 40
20 20
0 0
0 20 40 60 80 1.5 2 2.5 3 3.5 4
G J
Figure 3. Correlations between DN2S(4) or TOTOP vs. G, J, and F indices for all chemical graphs with
N ¼ 4, 5, and 6 vertices symbolizing carbon atoms.
indices lead to quasi-parallel lines in the corresponding diagram similarly to the

diagram with TOTOP versus F mentioned above.
By contrast, index G achieves a remarkable linear correlation with index DN2S(4)
with a correlation factor of over 0.99 for all 62 alkanes, all 92 acyclic and cyclic graphs
with 4–6 carbon atoms, and all the combined 62 þ 92 structures. This practically linear
correlation between indices G (2nd generation) and DN2S(4) (3rd generation) is due to
DN2S(4) vs G for alkanes C7-C9

55 TOTOP vs G for alkanes C7-C9
35
50 33
31
45 29
DN2S(4)
27
TOTOP
40
25
23
35
21
30 19
17
25 15
10 20 30 40 15 20 25
G G
DN2S(4) vs J = F for alkanes C7-C9 TOTOP vs J = F for alkanes C7-C9

55 27
50 25
45 23
DN2S(4)
TOTOP
40 21
35 19
30 17
25 15
2 3 4 5 2 2.5 3 3.5 4 4.5
J=F J=F
Figure 4. Correlations between DN2S(4) or TOTOP vs. G and J ¼ F indices for alkanes with N ¼ 7, 8, and
9 carbon atoms.
the practically linear correlation between their corresponding LOVIs, evidenced by

figure 5. In other words, the triplets DN2S or DN2N2 convert the integer distance sums
S into real-number LOVIs that are quasi-linearly correlated with S values, but have a
much lower degeneracy.
5. Degeneracy of the TIs discussed here
From the above considerations one can infer details about the degeneracy of the TIs
under discussion. None of the second and third generation TIs (J, F, G, DN2S(4), and
TOTOP) displays degeneracy for the limited number of hydrocarbon structures that
have been examined here. One should mention that for any set of structures involved in
biochemical contexts or QSAR studies, the nature of heteroatoms and multiple bonding
will be taken into account by index Jhet and then by the triplet indices derived from
Jhet, reducing further their degeneracy.
As mentioned earlier, the high degeneracy of the Wiener index W is observed from
tables 1 and 2. A hierarchical scale of decreasing degeneracy results for three groups of
TIs: index J orders alkanes very similarly to the highly-degenerated index W; in turn,
DN2S vs DN2N2 for hexanes& heptanes S vs DN2S for hexanes and heptanes
25
0.35
y = -x + 1.0004
0.3 R2 = 0.9985 20
0.25
DN2S
15
S
0.2
10
0.15
0.1 5
0.65 0.7 0.75 0.8 0.85 0.9 0.1 0.15 0.2 0.25 0.3 0.35
DN2N2 DN2S
Figure 5. Plots showing the intercorrelation of LOVIs (DN2S and DN2N2) and the correlation between
distance sums (S) and local vertex invariants (DN2S).
the triplet index DN2S(4) and index TOTOP that have extremely low degeneracy vary
quasi-linearly with index G (which, being derived from J, shares the same reduced
degeneracy that is lower than the degeneracy of W).
We now have three closely related second-generation indices (J, F, and G), which can
be easily adapted for chemical graphs by taking into account the presence of multiple
bonds and heteroatoms: the first one (J) compensates the influence of graph size and
cyclicity, accounting mainly for branching, and in QSAR/QSPR studies where the
property depends on size J should be accompanied by molecular descriptor(s) that take
size into account; index F varies with cyclicity and branching so that it reflects both
these influences; and index G, which varies with size, cyclicity and branching.
Interestingly, index G shows a quasi-linear variation with third-generation indices
DN2S(4) and TOTOP which have a much lower degeneracy. If we denote the
degeneracy of a topological index TI by DðTIÞ, the above hierarchical scale may be
expressed (according to decreasing degeneracy for first, second, and third generation
TIs) as:
DðWÞ>DðJÞ ¼ DðFÞ ¼ DðGÞ>DðDN2 Sð4ÞÞ DðTOTOPÞ
The ‘‘desirable’’ features of J (inherited by derived indices F and especially G) are

thus mimicked by the less degenerate triplet index DN2S(4), and any other similar
triplet index in which the main diagonal column vector N2 is replaced by another
vector with sufficiently large entries. This may be important for pharmaceutical
research companies, which can communicate properties of sets of compounds
through their TIs without disclosing actual chemical structures, because the ‘‘inverse
problem’’ of finding structures from TIs becomes impossible to carry out in
practice. From the numerous studies for solving ‘‘inverse problems’’ only a few
have been successful, namely for most first generation and a few second generation
TIs. If one wishes to make a triplet index even safer against ‘‘reverse engineering’’,
one can keep secret its three components (matrix and the two vectors) [69],
changing the matrix with other more complicated matrices such as the resistance
matrix [70–74] introduced by Klein and Randić [70].
It had been shown that index J starts to be degenerate for monocyclic graphs with
eight carbon atoms and acyclic graphs with 12 carbon atoms. There is one degeneracy
for DN2S(4) and none for TOTOP for all these graphs [69]. It was also shown earlier
[18] that all even-membered cycloalkanes have the same J ¼ 2.000 value.
6. QSAR and QSPR
We present a few examples in order to show that the newly introduced indices F and G
can be used in bi- and multi-parametric correlations with physical-chemical properties
(QSPR) or with biological activities (QSAR). The following correlations were obtained
using ordinary least squares (OLS) regression implemented in the PROC REG
procedure of the SAS statistical program [75]. For each correlation, both fitted and
cross-validated R2 values are reported. The latter is based on the leave-one-out (LOO)
approach and is calculated according to the following equation:

2 PRESS
rcv ¼ 1 ð6Þ
SSTotal
where PRESS is the prediction sum of squares, i.e., the sum of squares of the differences
between the actual observed activities and those predicted from the regression, and
SSTotal represents the total sum of squares. With respect to model validation, it has been
shown that the LOO approach is preferred over the use of a held-out test set when the
data set is small [76], as is true of the data sets analyzed in this paper. Problems
associated with the use of a held-out test set include: (1) Structural features present in
the held-out compounds are not included in the modeling process, resulting in a loss of
information; (2) predictions are made on only a subset of the compounds, whereas LOO
predicts the property or activity value for all compounds in the data set; (3) there is no
scientific tool that can guarantee similarity between the training set and the held-out test
set; (4) personal bias can easily be introduced in the selection of the held-out test set.
In addition to r2 and r2cv , the standard error of prediction (s) and the Fisher value (F) are
also reported for each correlation.
6.1 Normal boiling points of alkanes and cycloalkanes

Although many QSPR studies on this topic have been published (only recent references
are included here [77–82]), it is customary to show for new molecular descriptors how
they behave in correlations with a simple physical property that is measured accurately,
such as the boiling point at normal pressure (NBP). For 72 alkanes, 17 monocyclic and
10 bicyclic saturated hydrocarbons from figures 1 and 2 with the corresponding ID
numbers, the monoparametric and biparametric correlation results are presented in
table 4 and as Supplementary Material (table 4A). Please note, tables 4A to 8A for this
paper are posted online on the journal website http://www.tandf.co.uk/journals/listings/
s.asp under the heading ‘‘Supplementary material’’. Boiling points were obtained from
literature [78, 83] and are measured in C. One can see that in monoparametric
correlations the Wiener index W outperforms the other indices (J, F, and G) which were
designed to be used only in multiparametric correlations, but on including as a second
Table 4. Normal boiling point correlations for 99 saturated C4–C9 hydrocarbons, where NBP is
measured in C.
Independent variables r2 r2c:v: s F
Monoparametric correlations
J 0.527 0.510 29.3 108
F 0.104 0.068 40.4 11.3
JX 0.526 0.509 29.4 108
JY 0.526 0.509 29.4 108
W 0.895 0.890 13.8 828
G 0.655 0.643 25.0 184
MW 0.952 0.950 9.32 1932
Biparametric correlations
J þ MW 0.963 0.960 8.21 1259
F þ MW 0.961 0.958 8.41 1199
JX þ MW 0.963 0.961 8.19 1267
JY þ MW 0.963 0.961 8.19 1267
W þ MW 0.952 0.949 9.37 957
G þ MW 0.956 0.953 8.95 1054
Table 5. Normal boiling point correlations for 138 acyclic alcohols, where NBP is measured in C.
Independent variables r2 r2c:v: S F
J¼F 0.021 0.007 37.9 2.97
JX 0.014 0.014 38.0 1.96
JY 0.024 0.005 37.8 3.34
W 0.818 0.784 16.3 612
G 0.457 0.435 28.2 114
MW 0.867 0.863 13.9 891
(J ¼ F) þ MW 0.961 0.960 7.54 1687
JX þ MW 0.960 0.959 7.64 1642
JY þ MW 0.962 0.960 7.51 1701
W þ MW 0.891 0.877 12.7 552
G þ MW 0.963 0.961 7.42 1739
descriptor the molecular weight (MW), indices F and G perform similarly to W, and J
outperforms W. In the heading of table 4 and subsequent tables, the letter F stands for
Sir Ronald A. Fisher’s statistical parameter (the same letter is used for one of the newly
introduced topological indices).
6.2 Normal boiling points of alcohols

The following QSAR and QSPR data are for alcohols. Normal boiling points of 138
acyclic alcohols are presented in table 5 and as Supplementary Material (table 5A) using
the same approach and molecular descriptors for mono- and bi-parametric correlations
as in preceding case. Experimental data were obtained from ref. [84]. Because of the
presence of the oxygen heteroatom, index J is adjustable by means of a relative
electronegativity (JX) or a relative covalent radius (JY). From table 5 one can see that
Table 6. Solubility (log 1/S) correlations for 63 acyclic alcohols, where S is in moles per liter.
J¼F 0.023 0.055 1.0 1.43
JX 0.032 0.043 1.0 2.01
JY 0.020 0.058 1.0 1.26
W 0.877 0.813 0.36 433
G 0.572 0.451 0.68 81.4
MW 0.916 0.909 0.30 662
(J ¼ F) þ MW 0.967 0.965 0.19 905
JX þ MW 0.967 0.964 0.19 886
JY þ MW 0.968 0.965 0.19 911
W þ MW 0.943 0.921 0.25 496
G þ MW 0.963 0.958 0.20 788
correlations based on JY lead to better results. Again, the same conclusion can be drawn
about W versus the descriptors J, F, and G.
6.3 Aqueous solubility of alcohols

In table 6 and as Supplementary Material (table 6A) one may see the results of mono-
and bi-parametric QSPR correlations the aqueous solubility S of 63 acyclic alcohols,
expressed as log(1/S), where S is in moles per liter; the values span over five orders of
magnitude. Experimental data were obtained from Ren [84]; see also Duchowicz et al.
[85]. In this case the difference between the biparametric results for JX and JY is much
smaller than in the previous case.
6.4 Toxicity of alcohols

A final QSAR study compares experimental and calculated data for toxicities of 14
alcohols against plants (tomatoes) and animals (spiders). Toxicity is 50% inhibitory
growth impairment concentration (log LC50), with C representing molar concentra-
tion. Results are presented in tables 7 and 8, and as Supplementary Material (tables 7A
and 8A). Experimental data were obtained from Ren [84]; see also Junkes et al. [86].
Also in the present case the difference between the biparametric results for JX and JY is
smaller than for the boiling point correlation.
From all these QSPR and QSAR findings the same conclusion is obtained: in
monoparametric correlations, the Wiener index W outperforms the other indices (J, F,
and G) which were designed to be used only in multiparametric correlations, but on
including as a second descriptor the molecular weight (MW), the reverse is true.
Molecular descriptors were calculated with computer programs TRIPLET, POLLY
v2.3 [87], and Molconn-Z v3.5 [88].
7. Conclusions
The new second generation TIs introduced in this article (F and G, derived from
index J) present some interesting features: they inherit from index J both the low
Table 7. Alcohol tomato toxicity correlation results (acyclic compounds), where toxicity is 50% inhibitory
growth impairment concentration (log LC50) and C represents molar concentration.
J¼F 0.492 0.292 0.31 11.6
JX 0.521 0.343 0.30 13.0
JY 0.482 0.274 0.31 11.9
W 0.858 0.797 0.16 72.6
G 0.683 0.551 0.24 25.9
MW 0.878 0.841 0.15 76.8
(J ¼ F) þ MW 0.930 0.875 0.12 73.1
JX þ MW 0.928 0.872 0.12 70.4
JY þ MW 0.931 0.877 0.12 74.0
W þ MW 0.889 0.818 0.15 44.0
G þ MW 0.962 0.929 0.09 139
Table 8. Alcohol spider toxicity correlation results (acyclic compounds), where toxicity is 50% inhibitory
growth impairment concentration (log LC50) and C represents molar concentration.
J¼F 0.446 0.248 0.31 9.67
JX 0.474 0.299 0.30 10.4
JY 0.437 0.230 0.31 9.31
W 0.907 0.878 0.13 117
G 0.688 0.595 0.23 26.5
MW 0.877 0.843 0.15 85.5
(J ¼ F) þ MW 0.963 0.943 0.08 143
JX þ MW 0.961 0.939 0.09 135
JY þ MW 0.964 0.944 0.08 146
W þ MW 0.915 0.855 0.13 59.0
G þ MW 0.952 0.903 0.10 109
degeneracy and the correlation ability for molecular properties, in addition to the
possibility of including information on the presence of heteroatoms and multiple
bonding. Such properties of J were apparent in two recent examples, namely the
hundred-fold improvement of the biological activity of a lead compound (an
immunosuppressive decapeptide) [89], and the analysis of the RNA secondary structure
[90]. However, the new indices F and G allow the separation of graph size and cyclicity,
unlike the index J which had been designed to model mainly the branching (shape) of
chemical graphs. An interesting feature of index G is its high correlation with third
generation indices having extremely low degeneracy such as DN2S(4) and TOTOP,
which may be convenient for communication of molecular properties without disclosing
structures.
Indices F and G may find application also for describing molecular complexity, along
with other molecular descriptors [91–97].
Acknowledgements
The help of Dr. Greg Grunwald with the TRIPLET program is gratefully
acknowledged. Research reported in this paper was support, in part, by Grant
F49620-02-1-0138 from the United States Air Force and Cooperative Agreement
Number 572112 from the Agency for Toxic Substances and Disease Registry. This
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Supplementary Material
Table 4A. Normal b.p. of hydrocarbons.
Comp. No. Chemical name SMILES Class J Jx Jy F Fx Fy W G Gx
1 1 Butane CCCC Acyclic 1.97474 1.97474 1.97474 1.9747 1.97474 1.97474 10 6.3192 6.31917
2 2 2-Methylpropane CC(C)C Acyclic 2.32379 2.32379 2.32379 2.3238 2.32379 2.32379 9 7.4361 7.43613
3 3 Cyclobutane C1CCC1 Monocyclic 2 2 2 4 4 4 8 10.6667 10.66667
4 4 Methylcyclopropane CC1CC1 Monocyclic 2.1711 2.1711 2.1711 4.3422 4.3422 4.3422 8 11.5792 11.5792
90 5 Bicyclo[1.1.0]butane C12CC1C2 Bicyclic 2.48006 2.48006 2.48006 7.44018 7.44018 7.44018 7 17.00613 17.00613
5 7 Pentane CCCCC Acyclic 2.19061 2.19061 2.19061 2.1906 2.19061 2.19061 20 9.1275 9.12754
6 8 2-Methylbutane CC(C)CC Acyclic 2.53954 2.53954 2.53954 2.5395 2.53954 2.53954 18 10.5814 10.58142
7 9 2.2-Dimethylpropane CC(C)(C)C Acyclic 3.02372 3.02372 3.02372 3.0237 3.02372 3.02372 16 12.5988 12.59883
8 10 Cyclopentane C1CCCC1 Monocyclic 2.08333 2.08333 2.08333 4.1667 4.16666 4.16666 15 14.8809 14.88093
9 11 Methylcyclobutane CC1CCC1 Monocyclic 2.07967 2.07967 2.07967 4.1593 4.15934 4.15934 16 14.8548 14.85479
10 12 1.1-Dimethylcyclopropane CC1(C)CC1 Monocyclic 2.3822 2.3822 2.3822 4.7644 4.7644 4.7644 15 17.0157 17.01571
11 13 E-1.2-Dimethylcyclopropane CC1CC1C Monocyclic 2.20344 2.20344 2.20344 4.4069 4.40688 4.40688 16 15.7389 15.73886
12 14 Ethylcyclopropane CCC1CC1 Monocyclic 1.99894 1.99894 1.99894 3.9979 3.99788 3.99788 17 14.2781 14.27814
94 15 Bicyclo[2.1.0]cyclopentane C12CC1CC2 Bicyclic 2.19393 2.19393 2.19393 6.58179 6.58179 6.58179 14 20.56809 20.56809
92 18 Spiro[2.2]pentane C2CC12CC1 Bicyclic 2.29966 2.29966 2.29966 6.89898 6.89898 6.89898 14 21.55931 21.55931
93 19 Bicyclo[1.1.1]pentane C1C2CC1C2 Bicyclic 2.19089 2.19089 2.19089 6.57267 6.57267 6.57267 14 20.53959 20.53959
13 28 Hexane CCCCCC Acyclic 2.33909 2.33909 2.33909 2.3391 2.33909 2.33909 35 12.0296 12.02961
14 29 2-Methylpentane CC(C)CCC Acyclic 2.62721 2.62721 2.62721 2.6272 2.62721 2.62721 32 13.5114 13.51137
15 30 3-Methylpentane CCC(C)CC Acyclic 2.75418 2.75418 2.75418 2.7542 2.75418 2.75418 31 14.1644 14.16435
16 31 2.3-Dimethylbutane CC(C)C(C)C Acyclic 3.16849 2.9935 2.9935 3.1685 2.9935 2.9935 28 16.2951 15.39514
17 32 2.2-Dimethylbutane CC(C)(C)CC Acyclic 2.9935 3.16849 3.16849 2.9935 3.16849 3.16849 29 15.3951 16.29509
18 33 1.2.3-Trimethylcyclopropane CC1C(C)C1C Monocyclic 2.31136 2.31136 2.31136 4.6227 4.62272 4.62272 27 20.8022 20.80224
19 34 1.1.2-Trimethylcyclopropane CC1(C)CC1C Monocyclic 2.41329 2.41329 2.41329 4.8266 4.82658 4.82658 26 21.7196 21.71961
20 36 1-Ethyl-2-methylcyclopropane CCC1CC1C Monocyclic 2.09391 2.09391 2.09391 4.1878 4.18782 4.18782 29 18.8452 18.84519
21 37 Propylcyclopropane CCCC1CC1 Monocyclic 1.87629 1.87629 1.87629 3.7526 3.75258 3.75258 31 16.8866 16.88661
22 38 Isopropylcyclopeopane CC(C)C1CC1 Monocyclic 2.12947 2.12947 2.12947 4.2589 4.25894 4.25894 28 19.1652 19.16523
23 39 Ethylcyclobutane CCC1CCC1 Monocyclic 2.01427 2.01427 2.01427 4.0285 4.02854 4.02854 29 18.1284 18.12843
24 41 1.3-Dimethylcyclobutane CC1CC(C)C1 Monocyclic 2.11237 2.11237 2.11237 4.2247 4.22474 4.22474 28 19.0113 19.01133
25 42 1.2-Dimethylcyclobutane CC1CCC1C Monocyclic 2.2016 2.2016 2.2016 4.4032 4.4032 4.4032 27 19.8144 19.8144
26 43 Methylcyclopentane CC1CCCC1 Monocyclic 2.18411 2.18411 2.18411 4.3682 4.36822 4.36822 26 19.657 19.65699
27 44 Cyclohexane C1CCCCC1 Monocyclic 2 2 2 4 4 4 27 18 18
91 51 1-Methylbicyclo[2.1.0]pentane C2C1(C)CCC12 Bicyclic 2.21561 2.21561 2.21561 6.64683 6.64683 6.64683 24 26.58732 26.58732
98 54 2.4-Dimethyl-bicyclo C12C(C)C1C2C Bicyclic 2.05684 2.05684 2.05684 6.17052 6.17052 6.17052 27 24.68208 24.68208
[1.1.0]butane
97 56 Bicyclo[2.2.0]hexane C2C1CCC1C2 Bicyclic 2.02774 2.02774 2.02774 6.08322 6.08322 6.08322 25 24.33288 24.33288
96 57 Bicyclo[3.1.0]hexane C2C1CC1CC2 Bicyclic 2.09486 2.09486 2.09486 6.28458 6.28458 6.28458 24 25.13832 25.13832
95 58 Bis-cyclopropane C1CC1C2CC2 Bicyclic 1.91555 1.91555 1.91555 5.74665 5.74665 5.74665 27 22.9866 22.9866
99 59 Bicyclo[2.1.1]hexane C2C(C1)CCC12 Bicyclic 2.1625 2.1625 2.1625 6.4875 6.4875 6.4875 23 25.95 25.95
28 93 Heptane CCCCCCC Acyclic 2.44747 2.44747 2.44747 2.4475 2.44747 2.44747 56 14.9908 14.99075
29 94 2-Methylhexane CC(C)CCCC Acyclic 2.67826 2.67826 2.67826 2.6783 2.67826 2.67826 52 16.4043 16.40434
30 95 3-Methylhexane CCC(C)CCC Acyclic 2.83182 2.83182 2.83182 2.8318 2.83182 2.83182 50 17.3449 17.3449
31 96 2.4-Dimethylpentane CC(C)CC(C)C Acyclic 2.95322 2.95322 2.95322 2.9532 2.95322 2.95322 48 18.0885 18.08847
32 97 3-Ethylpentane CCC(CC)CC Acyclic 2.9923 2.9923 2.9923 2.9923 2.9923 2.9923 48 18.3278 18.32784
33 98 2.3-Dimethylpentane CC(C)C(C)CC Acyclic 3.14421 3.14421 3.14421 3.1442 3.14421 3.14421 46 19.2583 19.25829
34 99 2.2-Dimethylpentane CC(C)(C)CCC Acyclic 3.15449 3.15449 3.15449 3.1545 3.15449 3.15449 46 19.3213 19.32125
35 100 3.3-Dimethylpentane CCC(C)(C)CC Acyclic 3.36044 3.36044 3.36044 3.3604 3.36044 3.36044 44 20.5827 20.5827
36 101 2.2.3-Trimethylbutane CC(C)C(C)(C)C Acyclic 3.5412 3.5412 3.5412 3.5412 3.5412 3.5412 42 21.6899 21.68985
37 102 Octane CCCCCCCC Acyclic 2.53006 2.53006 2.53006 2.5301 2.53006 2.53006 84 17.9915 17.99154
38 103 2-Methylheptane CC(C)CCCCC Acyclic 2.71584 2.71584 2.71584 2.7158 2.71584 2.71584 79 19.3126 19.31264
39 104 3-Methylheptane CCC(C)CCCC Acyclic 2.86207 2.86207 2.86207 2.8621 2.86207 2.86207 76 20.3525 20.3525
40 105 4-Methylheptane CCCC(C)CCC Acyclic 2.91961 2.91961 2.91961 2.9196 2.91961 2.91961 75 20.7617 20.76167
2
Table 4A. Continued.
1 (J þ MW) 2 (Jx þ MW) 3 (Jy þ MW) 4 (W þ MW) 5 (G þ MW) 6 (Gx þ MW) 7 (Gy þ MW)
Calc Calc Calc Calc BP Calc Calc Calc

Gy DN2S(4) N R MW totop Exp BP BP Resid. BP Resid. BP Resid. ( C) Resid BP Resid. BP Resid BP Resid.
6.31917 14.1059 4 0 58.123 7.6483 0.1 15 15.1 15 15.1 15 15.1 14.8 14.9 10.3 10.4 10.3 10.4 10.3 10.4
7.43613 16.1558 4 0 58.123 7.7798 11.2 10.7 21.9 10.7 21.9 10.7 21.9 14.8 26 11.1 22.3 11.1 22.3 11.1 22.3
10.66667 20 4 1 56.107 11.3889 12.6 10.7 1.9 10.7 1.9 10.7 1.9 11.2 1.4 10.3 2.3 10.3 2.3 10.3 2.3
11.5792 22.0154 4 1 56.107 11.5574 0.7 8.6 7.9 8.5 7.8 8.5 7.8 11.2 10.5 11 10.3 11 10.3 11 10.3
17.00613 29.1852 4 2 54.091 16.37397 4.3 0.7 3.6 0.7 3.6 0.7 3.6 7.7 3.4 11.9 7.6 11.8 7.5 11.8 7.5
9.12754 18.455 5 0 72.15 10.5529 36.1 40.5 4.4 40.5 4.4 40.5 4.4 39.7 3.6 34.8 1.3 34.9 1.2 34.9 1.2
10.58142 20.8191 5 0 72.15 10.7935 27 36.3 9.3 36.2 9.2 36.2 9.2 39.7 12.7 35.9 8.9 35.9 8.9 35.9 8.9
12.59883 24.0703 5 0 72.15 11.0583 9.5 30.3 20.8 30.2 20.7 30.2 20.7 39.8 30.3 37.4 27.9 37.4 27.9 37.4 27.9
14.88093 25.8333 5 1 70.134 14.6361 49.3 37.8 11.5 37.8 11.5 37.8 11.5 36.2 13.1 35.9 13.4 35.9 13.4 35.9 13.4
14.85479 26.3617 5 1 70.134 14.984 36.3 37.8 1.5 37.9 1.6 37.9 1.6 36.2 0.1 35.9 0.4 35.9 0.4 35.9 0.4
17.01571 29.9076 5 1 70.134 15.3194 20.6 34.1 13.5 34.1 13.5 34.1 13.5 36.2 15.6 37.5 16.9 37.5 16.9 37.5 16.9
15.73886 28.1868 5 1 70.134 15.2749 33 36.3 3.3 36.3 3.3 36.3 3.3 36.2 3.2 36.6 3.6 36.6 3.6 36.6 3.6
14.27814 25.8889 5 1 70.134 14.8249 35.9 38.8 2.9 38.9 3 38.9 3 36.2 0.3 35.5 0.4 35.5 0.4 35.5 0.4
20.56809 33.67487 5 2 68.118 20.333 45.5 32.4 13.1 32.4 13.1 32.4 13.1 32.6 12.9 37 8.5 36.9 8.6 36.9 8.6
21.55931 35.42418 5 2 68.118 20.18504 39 31.1 7.9 31.1 7.9 31.1 7.9 32.6 6.4 37.7 1.3 37.7 1.3 37.7 1.3
20.53959 33.55433 5 2 68.118 20.47574 46 32.4 13.6 32.4 13.6 32.4 13.6 32.6 13.4 37 9 36.9 9.1 36.9 9.1
12.02961 22.7762 6 0 86.177 13.5229 68.8 66.9 1.9 66.9 1.9 66.9 1.9 64.4 4.4 59.4 9.4 59.5 9.3 59.5 9.3
13.51137 24.9765 6 0 86.177 13.8072 60.9 63.3 2.4 63.3 2.4 63.3 2.4 64.5 3.6 60.5 0.4 60.6 0.3 60.6 0.3
14.16435 26.0121 6 0 86.177 13.9209 63.3 61.8 1.5 61.8 1.5 61.8 1.5 64.5 1.2 61 2.3 61.1 2.2 61.1 2.2
15.39514 29.1928 6 0 86.177 14.294 58.1 56.7 1.4 58.8 0.7 58.8 0.7 64.6 6.5 62.6 4.5 62 3.9 62 3.9
16.29509 27.7239 6 0 86.177 14.16 49.8 58.9 9.1 56.6 6.8 56.6 6.8 64.6 14.8 62 12.2 62.7 12.9 62.7 12.9
20.80224 35.2972 6 1 84.161 19.3473 63 63.2 0.2 63.2 0.2 63.2 0.2 61 2 62.8 0.2 62.8 0.2 62.8 0.2
21.71961 36.4853 6 1 84.161 19.3796 54 61.9 7.9 61.9 7.9 61.9 7.9 61.1 7.1 63.5 9.5 63.5 9.5 63.5 9.5
18.84519 32.5498 6 1 84.161 18.7327 59 65.8 6.8 65.9 6.9 65.9 6.9 61 2 61.3 2.3 61.3 2.3 61.3 2.3
16.88661 29.5089 6 1 84.161 17.9935 69.1 68.5 0.6 68.6 0.5 68.6 0.5 60.9 8.2 59.9 9.2 59.9 9.2 59.9 9.2
19.16523 32.5627 6 1 84.161 18.4576 58.3 65.4 7.1 65.4 7.1 65.4 7.1 61 2.7 61.6 3.3 61.6 3.3 61.6 3.3
18.12843 31.1401 6 1 84.161 18.3798 70.8 66.8 4 66.9 3.9 66.9 3.9 61 9.8 60.8 10 60.8 10 60.8 10
19.01133 32.3816 6 1 84.161 18.8118 57.5 65.6 8.1 65.6 8.1 65.6 8.1 61 3.5 61.5 4 61.5 4 61.5 4
19.8144 33.3904 6 1 84.161 18.8868 59 64.5 5.5 64.5 5.5 64.5 5.5 61 2 62.1 3.1 62.1 3.1 62.1 3.1
19.65699 32.7274 6 1 84.161 18.3709 71.9 64.7 7.2 64.8 7.1 64.8 7.1 61.1 10.8 61.9 10 61.9 10 61.9 10
18 30 6 1 84.161 17.8967 80.8 67 13.8 67 13.8 67 13.8 61 19.8 60.7 20.1 60.7 20.1 60.7 20.1
26.58732 42.12589 6 2 82.145 25.09486 80 60.3 19.7 60.3 19.7 60.3 19.7 57.5 22.5 63.9 16.1 63.9 16.1 63.9 16.1
24.68208 40.548 6 2 82.145 25.51277 54.4 62.2 7.8 62.3 7.9 62.3 7.9 57.4 3 62.5 8.1 62.5 8.1 62.5 8.1
24.33288 38.69884 6 2 82.145 24.40979 80 62.6 17.4 62.6 17.4 62.6 17.4 57.5 22.5 62.2 17.8 62.2 17.8 62.2 17.8
25.13832 39.63475 6 2 82.145 24.14334 81 61.8 19.2 61.8 19.2 61.8 19.2 57.5 23.5 62.9 18.1 62.8 18.2 62.8 18.2
22.9866 37.23669 6 2 82.145 23.12237 76.2 64 12.2 64 12.2 64 12.2 57.4 18.8 61.2 15 61.2 15 61.2 15
25.95 40.5017 6 2 82.145 24.42163 71 60.9 10.1 61 10 61 10 57.6 13.4 63.5 7.5 63.4 7.6 63.4 7.6
14.99075 27.0827 7 0 100.203 16.5385 98.5 93.7 4.8 93.7 4.8 93.7 4.8 88.8 9.7 84.1 14.4 84.1 14.4 84.1 14.4
16.40434 29.0301 7 0 100.203 16.846 90.1 90.9 0.8 90.9 0.8 90.9 0.8 89 1.1 85.2 4.9 85.2 4.9 85.2 4.9
17.3449 30.4562 7 0 100.203 17.0048 91.8 89 2.8 89 2.8 89 2.8 89.1 2.7 85.9 5.9 85.9 5.9 85.9 5.9
18.08847 31.2886 7 0 100.203 17.1763 80.6 87.5 6.9 87.5 6.9 87.5 6.9 89.1 8.5 86.4 5.8 86.4 5.8 86.4 5.8
18.32784 31.8548 7 0 100.203 17.1618 93.5 87 6.5 87 6.5 87 6.5 89.1 4.4 86.6 6.9 86.6 6.9 86.6 6.9
19.25829 33.0705 7 0 100.203 17.4067 89.8 85.2 4.6 85.1 4.7 85.1 4.7 89.2 0.6 87.3 2.5 87.3 2.5 87.3 2.5
19.32125 33.2603 7 0 100.203 17.4218 79.2 85 5.8 85 5.8 85 5.8 89.2 10 87.3 8.1 87.4 8.2 87.4 8.2
20.5827 35.0656 7 0 100.203 17.6511 86.1 82.5 3.6 82.5 3.6 82.5 3.6 89.3 3.2 88.3 2.2 88.3 2.2 88.3 2.2
21.68985 36.4332 7 0 100.203 17.8913 81 80.3 0.7 80.2 0.8 80.2 0.8 89.3 8.3 89.1 8.1 89.1 8.1 89.1 8.1
17.99154 31.3804 8 0 114.23 19.588 125.6 120.8 4.8 120.9 4.7 120.9 4.7 113 12.6 108.8 16.8 108.8 16.8 108.8 16.8
19.31264 33.0884 8 0 114.23 19.9096 117.6 118.6 1 118.6 1 118.6 1 113.2 4.4 109.8 7.8 109.8 7.8 109.8 7.8
20.3525 34.5993 8 0 114.23 20.0921 118.9 116.8 2.1 116.8 2.1 116.8 2.1 113.3 5.6 110.6 8.3 110.6 8.3 110.6 8.3
20.76167 35.2215 8 0 114.23 20.1372 117.8 116.1 1.7 116.1 1.7 116.1 1.7 113.4 4.4 110.9 6.9 110.9 6.9 110.9 6.9
20.82005 34.9776 8 0 114.23 20.2416 109 116 7 116 7 116 7 113.4 4.4 110.9 1.9 110.9 1.9 110.9 1.9
3
Comp. No. Chemical name SMILES Class J Jx Jy F Fx Fy W G Gx
41 106 2.5-Dimethylhexane CC(C)CCC(C)C Acyclic 2.92782 2.92782 2.92782 2.9278 2.92782 2.92782 74 20.8201 20.82005
42 107 3-Ethylhexane CCC(CC)CCC Acyclic 3.07437 3.07437 3.07437 3.0744 3.07437 3.07437 72 21.8622 21.86219
43 108 2.4-Dimethylhexane CC(C)CC(C)CC Acyclic 3.09883 3.09883 3.09883 3.0988 3.09883 3.09883 71 22.0361 22.03612
44 109 2.2-Dimethylhexane CC(C)(C)CCCC Acyclic 3.11177 3.11177 3.11177 3.1118 3.11177 3.11177 71 22.1281 22.12814
45 110 2.3-Dimethylhexane CC(C)C(C)CCC Acyclic 3.17082 3.17082 3.17082 3.1708 3.17082 3.17082 70 22.5481 22.54805
46 111 3.4-Dimethylhexane CCC(C)C(C)CC Acyclic 3.29248 3.29248 3.29248 3.2925 3.29248 3.29248 68 23.4132 23.41319
47 112 3-Ethyl-2-methylpentane CC(C)C(CC)CC Acyclic 3.35488 3.35488 3.35488 3.3549 3.35488 3.35488 67 23.8569 23.85692
48 113 3.3-Dimethylhexane CCC(C)(C)CCC Acyclic 3.37338 3.37338 3.37338 3.3734 3.37338 3.37338 67 23.9885 23.98848
49 114 2.2.4-Trimethylpentane CC(C)(C)CC(C)C Acyclic 3.38892 3.38892 3.38892 3.3889 3.38892 3.38892 66 24.099 24.09899
50 115 2.3.4-Trimethylpentane CC(C)C(C)C(C)C Acyclic 3.46423 3.46423 3.46423 3.4642 3.46423 3.46423 65 24.6345 24.63452
51 116 3-Ethyl-3-methylpentane CCC(C)(CC)CC Acyclic 3.58321 3.58321 3.58321 3.5832 3.58321 3.58321 64 25.4806 25.4806
52 117 2.2.3-Trimethylpentane CC(C)(C)C(C)CC Acyclic 3.62328 3.62328 3.62328 3.6233 3.62328 3.62328 63 25.7656 25.76555
53 118 2.3.3-Trimethylpentane CC(C)C(C)(C)CC Acyclic 3.70832 3.70832 3.70832 3.7083 3.70832 3.70832 62 26.3703 26.37028
54 119 2.2.3.3-Tetramethylbutane CC(C)(C)C(C)(C)C Acyclic 4.02039 4.02039 4.02039 4.0204 4.02039 4.02039 58 28.5894 28.58944
55 120 Nonane CCCCCCCCC Acyclic 2.59508 2.59508 2.59508 2.5951 2.59508 2.59508 120 21.0202 21.02015
56 121 2-Methyloctane CC(C)CCCCCC Acyclic 2.74669 2.74669 2.74669 2.7467 2.74669 2.74669 114 22.2482 22.24819
57 122 3-Methyloctane CCC(C)CCCCC Acyclic 2.87662 2.87662 2.87662 2.8766 2.87662 2.87662 110 23.3006 23.30062
58 123 2.6-Dimethylheptane CC(C)CCCC(C)C Acyclic 2.91466 2.91466 2.91466 2.9147 2.91466 2.91466 108 23.6088 23.60875
59 124 4-Methyloctane CCCC(C)CCCC Acyclic 2.95482 2.95482 2.95482 2.9548 2.95482 2.95482 108 23.934 23.93404
60 125 2.5-Dimethylheptane CC(C)CCC(C)CC Acyclic 3.06082 3.06082 3.06082 3.0608 3.06082 3.06082 104 24.7926 24.79264
61 126 2.2-Dimethylheptane CC(C)(C)CCCCC Acyclic 3.07299 3.07299 3.07299 3.073 3.07299 3.07299 104 24.8912 24.89122
62 127 3-Ethylheptane CCC(CC)CCCC Acyclic 3.09225 3.09225 3.09225 3.0923 3.09225 3.09225 104 25.0472 25.04723
63 128 2.4-Dimethylheptane CC(C)CC(C)CCC Acyclic 3.15125 3.15125 3.15125 3.1513 3.15125 3.15125 102 25.5251 25.52513
64 129 2.3-Dimethylheptane CC(C)C(C)CCCC Acyclic 3.15528 3.15528 3.15528 3.1553 3.15528 3.15528 102 25.5578 25.55777
65 130 4-Ethylheptane CCCC(CC)CCC Acyclic 3.17534 3.17534 3.17534 3.1753 3.17534 3.17534 102 25.7203 25.72025
66 131 3.5-Dimethylheptane CCC(C)CC(C)CC Acyclic 3.22305 3.22305 3.22305 3.2231 3.22305 3.22305 100 26.1067 26.10671
67 132 2.2.5-Trimethylhexane CC(C)(C)CCC(C)C Acyclic 3.28071 3.28071 3.28071 3.2807 3.28071 3.28071 98 26.5738 26.57375
68 133 4-Ethyl-2-methylhexane CC(C)CC(CC)CC Acyclic 3.30739 3.30739 3.30739 3.3074 3.30739 3.30739 98 26.7899 26.78986
69 134 3.4-Dimethylheptane CCC(C)C(C)CCC Acyclic 3.32476 3.32476 3.32476 3.3248 3.32476 3.32476 98 26.9306 26.93056
70 135 3.3-Dimethylheptane CCC(C)(C)CCCC Acyclic 3.33007 3.33007 3.33007 3.3301 3.33007 3.33007 98 26.9736 26.97357
71 136 2.3.5-Trimethylhexane CC(C)C(C)CC(C)C Acyclic 3.3766 3.3766 3.3766 3.3766 3.3766 3.3766 96 27.3505 27.35046
72 137 3-Ethyl-2-methylhexane CC(C)C(CC)CCC Acyclic 3.41009 3.41009 3.41009 3.4101 3.41009 3.41009 96 27.6217 27.62173
73 138 4.4-Dimethylheptane CCCC(C)(C)CCC Acyclic 3.43105 3.43105 3.43105 3.4311 3.43105 3.43105 96 27.7915 27.79151
74 139 2.2.4-Trimethylhexane CC(C)(C)CC(C)CC Acyclic 3.46726 3.46726 3.46726 3.4673 3.46726 3.46726 94 28.0848 28.08481
75 140 3-Ethyl-4-methylhexane CCC(CC)C(C)CC Acyclic 3.49948 3.49948 3.49948 3.4995 3.49948 3.49948 94 28.3458 28.34579
76 141 2.3.4-Trimethylhexane CC(C)C(C)C(C)CC Acyclic 3.57583 3.57583 3.57583 3.5758 3.57583 3.57583 92 28.9642 28.96422
77 142 2.4.4-Trimethylhexane CC(C)CC(C)(C)CC Acyclic 3.57675 3.57675 3.57675 3.5768 3.57675 3.57675 92 28.9717 28.97168
78 143 2.2.3-Trimethylhexane CC(C)(C)C(C)CCC Acyclic 3.58873 3.58873 3.58873 3.5887 3.58873 3.58873 92 29.0687 29.06871
79 144 3-Ethyl-3-methylhexane CCC(C)(CC)CCC Acyclic 3.61739 3.61739 3.61739 3.6174 3.61739 3.61739 92 29.3009 29.30086
80 145 3-Ethyl-2.4-dimethylpentane CC(C)C(CC)C(C)C Acyclic 3.67762 3.67762 3.67762 3.6776 3.67762 3.67762 90 29.7887 29.78872
81 146 2.3.3-Trimethylhexane CC(C)C(C)(C)CCC Acyclic 3.70209 3.70209 3.70209 3.7021 3.70209 3.70209 90 29.9869 29.98693
82 147 2.2.4.4-Tetramethylpentane CC(C)(C)CC(C)(C)C Acyclic 3.74642 3.74642 3.74642 3.7464 3.74642 3.74642 88 30.346 30.346
83 148 3-Ethyl-2.2-dimethylpentane CC(C)(C)C(CC)CC Acyclic 3.79291 3.79291 3.79291 3.7929 3.79291 3.79291 88 30.7226 30.72257
84 149 3.3.4-Trimethylhexane CCC(C)(C)C(C)CC Acyclic 3.8024 3.8024 3.8024 3.8024 3.8024 3.8024 88 30.7994 30.79944
85 150 3.3-Diethylpentane CCC(CC)(CC)CC Acyclic 3.82468 3.82468 3.82468 3.8247 3.82468 3.82468 88 30.9799 30.97991
86 151 2.2.3.4-Tetramethylpentane CC(C)(C)C(C)C(C)C Acyclic 3.8776 3.8776 3.8776 3.8776 3.8776 3.8776 86 31.4086 31.40856
87 152 3-Ethyl-2.3-dimethylpentane CC(C)C(C)(CC)CC Acyclic 3.91921 3.91921 3.91921 3.9192 3.91921 3.91921 86 31.7456 31.7456
88 153 2.3.3.4-Tetramethylpentane CC(C)C(C)(C)C(C)C Acyclic 4.01374 4.01374 4.01374 4.0137 4.01374 4.01374 84 32.5113 32.51129
89 154 2.2.3.3-Tetramethylpentane CC(C)(C)C(C)(C)CC Acyclic 4.14473 4.14473 4.14473 4.1447 4.14473 4.14473 82 33.5723 33.57231
4
Calc Calc Calc Calc BP Calc Calc Calc

Gy DN2S4 N R MW totop Exp BP BP Resid. BP Resid. BP Resid. ( C) Resid BP Resid. BP Resid BP Resid.
20.82005 34.9776 8 0 114.23 20.2416 109 116 7 116 7 116 7 113.4 4.4 110.9 1.9 110.9 1.9 110.9 1.9
21.86219 36.6926 8 0 114.23 20.316 118.6 114.2 4.4 114.2 4.4 114.2 4.4 113.5 5.1 111.7 6.9 111.7 6.9 111.7 6.9
22.03612 36.7279 8 0 114.23 20.4478 108.9 113.9 5 113.9 5 113.9 5 113.5 4.6 111.8 2.9 111.8 2.9 111.8 2.9
22.12814 37.0142 8 0 114.23 20.5323 106.9 113.7 6.8 113.7 6.8 113.7 6.8 113.5 6.6 111.9 5 111.9 5 111.9 5
22.54805 37.5565 8 0 114.23 20.5646 115.9 113 2.9 113 2.9 113 2.9 113.6 2.3 112.2 3.7 112.2 3.7 112.2 3.7
23.41319 38.7162 8 0 114.23 20.7289 117.9 111.5 6.4 111.5 6.4 111.5 6.4 113.6 4.3 112.9 5 112.9 5 112.9 5
23.85692 39.2915 8 0 114.23 20.767 115.7 110.7 5 110.7 5 110.7 5 113.7 2 113.2 2.5 113.2 2.5 113.2 2.5
23.98848 39.6316 8 0 114.23 20.8528 112 110.5 1.5 110.5 1.5 110.5 1.5 113.7 1.7 113.3 1.3 113.3 1.3 113.3 1.3
24.09899 39.4498 8 0 114.23 20.9107 99.3 110.3 11 110.3 11 110.3 11 113.7 14.4 113.4 14.1 113.4 14.1 113.4 14.1
24.63452 40.2085 8 0 114.23 21.0178 113.7 109.4 4.3 109.4 4.3 109.4 4.3 113.7 0 113.8 0.1 113.8 0.1 113.8 0.1
25.4806 41.6165 8 0 114.23 21.1295 118.4 107.9 10.5 107.9 10.5 107.9 10.5 113.8 4.6 114.4 4 114.4 4 114.4 4
25.76555 41.8433 8 0 114.23 21.2626 110 107.5 2.5 107.4 2.6 107.4 2.6 113.8 3.8 114.6 4.6 114.6 4.6 114.6 4.6
26.37028 42.6852 8 0 114.23 21.3756 114.7 106.4 8.3 106.3 8.4 106.3 8.4 113.9 0.8 115.1 0.4 115.1 0.4 115.1 0.4
28.58944 45.5149 8 0 114.23 21.8632 106.5 102.6 3.9 102.5 4 102.5 4 114 7.5 116.8 10.3 116.7 10.2 116.7 10.2
21.02015 35.6724 9 0 128.257 22.6638 150.7 148.2 2.5 148.3 2.4 148.3 2.4 137 13.7 133.5 17.2 133.5 17.2 133.5 17.2
22.24819 37.1759 9 0 128.257 22.9946 143 146.3 3.3 146.4 3.4 146.4 3.4 137.2 5.8 134.4 8.6 134.4 8.6 134.4 8.6
23.30062 38.644 9 0 128.257 23.1914 143.9 144.7 0.8 144.8 0.9 144.8 0.9 137.3 6.6 135.2 8.7 135.2 8.7 135.2 8.7
23.60875 38.7891 9 0 128.257 23.3311 134.9 144.3 9.4 144.3 9.4 144.3 9.4 137.4 2.5 135.4 0.5 135.5 0.6 135.5 0.6
23.93404 39.5842 9 0 128.257 23.2603 141.9 143.8 1.9 143.8 1.9 143.8 1.9 137.4 4.5 135.7 6.2 135.7 6.2 135.7 6.2
24.79264 40.4139 9 0 128.257 23.5386 134.9 142.5 7.6 142.5 7.6 142.5 7.6 137.5 2.6 136.3 1.4 136.3 1.4 136.3 1.4
24.89122 40.7256 9 0 128.257 23.6457 131.9 142.3 10.4 142.4 10.5 142.4 10.5 137.5 5.6 136.4 4.5 136.4 4.5 136.4 4.5
25.04723 41.0104 9 0 128.257 23.4518 143.3 142.1 1.2 142.1 1.2 142.1 1.2 137.5 5.8 136.5 6.8 136.5 6.8 136.5 6.8
25.52513 41.519 9 0 128.257 23.6311 132.9 141.4 8.5 141.4 8.5 141.4 8.5 137.6 4.7 136.9 4 136.9 4 136.9 4
25.55777 41.6323 9 0 128.257 23.7028 139.9 141.3 1.4 141.4 1.5 141.4 1.5 137.6 2.3 136.9 3 136.9 3 136.9 3
25.72025 41.9303 9 0 128.257 23.5187 141.3 141.1 0.2 141.1 0.2 141.1 0.2 137.6 3.7 137 4.3 137 4.3 137 4.3
26.10671 42.2205 9 0 128.257 23.7708 135.6 140.5 4.9 140.5 4.9 140.5 4.9 137.7 2.1 137.3 1.7 137.3 1.7 137.3 1.7
26.57375 42.6734 9 0 128.257 24.0034 123.9 139.8 15.9 139.8 15.9 139.8 15.9 137.8 13.9 137.7 13.8 137.7 13.8 137.7 13.8
26.78986 43.1125 9 0 128.257 23.8329 133.8 139.5 5.7 139.5 5.7 139.5 5.7 137.8 4 137.8 4 137.8 4 137.8 4
26.93056 43.4692 9 0 128.257 23.9383 140.5 139.3 1.2 139.3 1.2 139.3 1.2 137.8 2.7 137.9 2.6 137.9 2.6 137.9 2.6
26.97357 43.6081 9 0 128.257 24.014 136.9 139.2 2.3 139.2 2.3 139.2 2.3 137.8 0.9 138 1.1 138 1.1 138 1.1
27.35046 43.752 9 0 128.257 24.0853 130.9 138.6 7.7 138.6 7.7 138.6 7.7 137.8 6.9 138.3 7.4 138.3 7.4 138.3 7.4
27.62173 44.3391 9 0 128.257 23.9951 138 138.2 0.2 138.2 0.2 138.2 0.2 137.8 0.2 138.5 0.5 138.5 0.5 138.5 0.5
27.79151 44.7453 9 0 128.257 24.1051 134.9 138 3.1 138 3.1 138 3.1 137.8 2.9 138.6 3.7 138.6 3.7 138.6 3.7
28.08481 44.7294 9 0 128.257 24.2593 126.5 137.5 11 137.5 11 137.5 11 137.9 11.4 138.8 12.3 138.8 12.3 138.8 12.3
28.34579 45.2576 9 0 128.257 24.1648 140.4 137.1 3.3 137.1 3.3 137.1 3.3 137.9 2.5 139 1.4 139 1.4 139 1.4
28.96422 45.9587 9 0 128.257 24.4195 138.9 136.2 2.7 136.2 2.7 136.2 2.7 138 0.9 139.5 0.6 139.5 0.6 139.5 0.6
28.97168 45.9761 9 0 128.257 24.4196 130.9 136.2 5.3 136.2 5.3 136.2 5.3 138 7.1 139.5 8.6 139.5 8.6 139.5 8.6
29.06871 46.2421 9 0 128.257 24.4976 133.1 136 2.9 136 2.9 136 2.9 138 4.9 139.5 6.4 139.5 6.4 139.5 6.4
29.30086 46.6711 9 0 128.257 24.4052 140.6 135.7 4.9 135.7 4.9 135.7 4.9 138 2.6 139.7 0.9 139.7 0.9 139.7 0.9
29.78872 47.0194 9 0 128.257 24.4974 136.7 134.9 1.8 134.9 1.8 134.9 1.8 138.1 1.4 140.1 3.4 140.1 3.4 140.1 3.4
29.98693 47.494 9 0 128.257 24.6551 137.1 134.6 2.5 134.6 2.5 134.6 2.5 138.1 1 140.2 3.1 140.2 3.1 140.2 3.1
30.346 47.5305 9 0 128.257 24.7705 122.3 134.1 11.8 134.1 11.8 134.1 11.8 138.1 15.8 140.5 18.2 140.5 18.2 140.5 18.2
30.72257 48.3109 9 0 128.257 24.7476 133.8 133.5 0.3 133.5 0.3 133.5 0.3 138.1 4.3 140.8 7 140.8 7 140.8 7
30.79944 48.4815 9 0 128.257 24.8266 140.2 133.4 6.8 133.4 6.8 133.4 6.8 138.1 2.1 140.9 0.7 140.8 0.6 140.8 0.6
30.97991 48.8002 9 0 128.257 24.7293 146.2 133.1 13.1 133.1 13.1 133.1 13.1 138.1 8.1 141 5.2 141 5.2 141 5.2
31.40856 49.0421 9 0 128.257 25.0046 133 132.5 0.5 132.4 0.6 132.4 0.6 138.2 5.2 141.3 8.3 141.3 8.3 141.3 8.3
31.7456 49.7047 9 0 128.257 24.9813 141.6 132 9.6 131.9 9.7 131.9 9.7 138.2 3.4 141.6 0 141.5 0.1 141.5 0.1
32.51129 50.5703 9 0 128.257 25.2335 141.5 130.8 10.7 130.8 10.7 130.8 10.7 138.3 3.2 142.1 0.6 142.1 0.6 142.1 0.6
33.57231 51.9849 9 0 128.257 25.4803 140.3 129.2 11.1 129.1 11.2 129.1 11.2 138.4 1.9 142.9 2.6 142.9 2.6 142.9 2.6
5
Table 5A. Normal b.p. of alcohols.
Model 1
(J þ MW)
No. Chemical name J¼F Fx ¼ Jx Fy ¼ Jy W G Gx Gy N R MW Exp BP ( C) Calc BP ( C) Residual
1 1-Butanol 2.19061 2.13232 2.20961 20 9.12754 8.88467 9.20671 5 0 74.12 117.6 123.3 5.7
2 2-Methyl-1-propanol 2.53954 2.47317 2.56118 18 10.58142 10.30488 10.67158 5 0 74.12 107.9 113.4 5.5
3 2-Butanol 2.53954 2.46242 2.56468 18 10.58142 10.26008 10.68617 5 0 74.12 99.5 113.4 13.9
4 2-Methyl-2-propanol 3.02372 2.93155 3.05376 16 12.59883 12.21479 12.724 5 0 74.12 82.4 99.6 17.2
5 1-Pentanol 2.33909 2.29163 2.35457 35 12.02961 11.78553 12.10922 6 0 88.15 137.5 137.4 0.1
6 3-Methyl-1-butanol 2.62721 2.57569 2.64401 32 13.51137 13.24641 13.59777 6 0 88.15 131 129.2 1.8
7 2-Pentanol 2.62721 2.56499 2.6475 32 13.51137 13.19138 13.61571 6 0 88.15 119.3 129.2 9.9
8 2-Methyl-1-butanol 2.75418 2.69782 2.77256 31 14.16435 13.8745 14.25888 6 0 88.15 128 125.6 2.4
9 3-Pentanol 2.75418 2.68471 2.77683 31 14.16435 13.80708 14.28084 6 0 88.15 116.2 125.6 9.4
10 3-Methyl-2-butanol 2.9935 2.92402 3.01615 29 15.39514 15.03782 15.51163 6 0 88.15 112.9 118.8 5.9
11 2.2-Dimethyl-1-propanol 3.16849 3.10627 3.18877 28 16.29509 15.9751 16.39939 6 0 88.15 113.1 113.8 0.7
12 2-Methyl-2-butanol 3.16849 3.08979 3.19415 28 16.29509 15.89035 16.42706 6 0 88.15 102.3 113.8 11.5
13 1-Hexanol 2.44747 2.40756 2.46048 56 14.99075 14.74631 15.07044 7 0 102.18 157 152.6 4.4
14 4-Methyl-1-pentanol 2.67826 2.63602 2.69203 52 16.40434 16.14562 16.48868 7 0 102.18 151.9 146.1 5.8
15 2-Hexanol 2.67826 2.62704 2.69496 52 16.40434 16.09062 16.50663 7 0 102.18 140 146.1 6.1
16 3-Methyl-1-pentanol 2.83182 2.78696 2.84644 50 17.3449 17.07013 17.43445 7 0 102.18 153 141.7 11.3
17 2-Methyl-1-pentanol 2.83182 2.784 2.84741 50 17.3449 17.052 17.44039 7 0 102.18 148 141.7 6.3
18 3-Hexanol 2.83182 2.77209 2.85129 50 17.3449 16.97905 17.46415 7 0 102.18 135 141.7 6.7
19 2-Ethyl-1-butanol 2.9923 2.94108 3.009 48 18.32784 18.01412 18.43013 7 0 102.18 146.5 137.2 9.3
20 4-Methyl-2-pentanol 2.95322 2.89808 2.9712 48 18.08847 17.75074 18.1986 7 0 102.18 132 138.3 6.3
21 3.3-Dimethyl-1-butanol 3.15449 3.10667 3.17008 46 19.32125 19.02835 19.41674 7 0 102.18 143 132.5 10.5
22 2.3-Dimethyl-1-butanol 3.14421 3.09299 3.16091 46 19.25829 18.94456 19.36057 7 0 102.18 144.5 132.8 11.7
23 2-Methyl-2-pentanol 3.15449 3.08932 3.17574 46 19.32125 18.92209 19.45141 7 0 102.18 121.5 132.5 11
24 3-Methyl-2-pentanol 3.14421 3.08448 3.16368 46 19.25829 18.89244 19.37754 7 0 102.18 134.3 132.8 1.5
25 2-Methyl-3-pentanol 3.14421 3.07903 3.16546 46 19.25829 18.85906 19.38844 7 0 102.18 129.5 132.8 3.3
26 2.2-dimethyl-1-butanol 3.36044 3.30529 3.37841 44 20.5827 20.2449 20.69276 7 0 102.18 136.5 126.7 9.8
27 3-Methyl-3-pentanol 3.36044 3.2887 3.38382 44 20.5827 20.14329 20.7259 7 0 102.18 123 126.7 3.7
30 1-Heptanol 2.53006 2.49567 2.54127 84 17.99154 17.74699 18.07125 8 0 116.2 176.4 168.6 7.8
31 5-Methyl-1-hexanol 2.71584 2.68 2.72753 79 19.31264 19.05778 19.39577 8 0 116.2 170 163.3 6.7
32 2-Heptanol 2.71584 2.67268 2.72991 79 19.31264 19.00572 19.41269 8 0 116.2 160.4 163.3 2.9
33 4-Methyl-1-hexanol 2.86207 2.82464 2.87427 76 20.3525 20.08633 20.43925 8 0 116.2 173.3 159.2 14.1
34 2-Methyl-1-hexanol 2.86207 2.821 2.87545 76 20.3525 20.06044 20.44764 8 0 116.2 164 159.2 4.8
35 3-Heptanol 2.86207 2.81106 2.87869 76 20.3525 19.98976 20.47068 8 0 116.2 157 159.2 2.2
36 3-Methyl-1-hexanol 2.91961 2.88045 2.93238 75 20.76167 20.4832 20.85248 8 0 116.2 169 157.5 11.5
37 4-Heptanol 2.91961 2.86531 2.93732 75 20.76167 20.37554 20.88761 8 0 116.2 156 157.5 1.5
38 5-Methyl-2-hexanol 2.92782 2.88233 2.94265 74 20.82005 20.49657 20.92551 8 0 116.2 151 157.3 6.3
39 2-Methyl-3-hexanol 3.17082 3.11275 3.18975 70 22.54805 22.13511 22.68267 8 0 116.2 145.5 150.4 4.9
40 2-Methyl-2-hexanol 3.11177 3.05746 3.12947 71 22.12814 21.74194 22.25401 8 0 116.2 143 152.1 9.1
41 2.4-Dimethyl-1-pentanol 3.09883 3.05566 3.1129 71 22.03612 21.72914 22.13618 8 0 116.2 159 152.4 6.6
42 5-Methyl-3-hexanol 3.09883 3.04452 3.11653 71 22.03612 21.64992 22.16199 8 0 116.2 148 152.4 4.4
43 3-Methyl-3-hexanol 3.37338 3.31097 3.39373 67 23.98848 23.54468 24.13319 8 0 116.2 143 144.6 1.6
44 2.4-Dimethyl-2-pentanol 3.38892 3.33085 3.40786 66 24.09899 23.68604 24.23367 8 0 116.2 133.1 144.2 11.1
46 3-Ethyl-3-pentanol 3.58321 3.51574 3.60521 64 25.4806 25.00082 25.63705 8 0 116.2 142 138.7 3.3
49 2.3.3-Trimethyl-2-butanol 4.02039 3.95292 4.04239 58 28.58944 28.10965 28.74588 8 0 116.2 130.5 126.2 4.3
50 3-Methyl-2-hexanol 3.17082 3.11981 3.18745 70 22.54805 22.18532 22.66631 8 0 116.2 151 150.4 0.6
51 1-Octanol 2.59508 2.56489 2.60492 120 21.02015 20.77561 21.09985 9 0 130.23 195.2 185.1 10.1
52 6-Methyl-1-heptanol 2.74669 2.71553 2.75685 114 22.24819 21.99579 22.33049 9 0 130.23 188.6 180.8 7.8
53 2-Octanol 2.74669 2.70956 2.7588 114 22.24819 21.94744 22.34628 9 0 130.23 180 180.8 0.8
54 3-Octanol 2.87662 2.83274 2.89093 110 23.30062 22.94519 23.41653 9 0 130.23 175 177.1 2.1
6
Model 2 Model 3 Model 4 Model 5 Model 6 Model 7

(Jx þ MW) (Jy þ MW) (W þ MW) (G þ MW) (Gx þ MW) (Gy þ MW)
Calc BP Calc BP Calc BP Calc Calc Calc

( C) Residual ( C) Residual ( C) Residual BP ( C) Residual BP ( C) Residual BP ( C) Residual
123.4 5.8 123.3 5.7 110.5 7.1 112.9 4.7 112.7 4.9 112.9 4.7
113.5 5.6 113.3 5.4 110.2 2.3 108 0.1 107.8 0.1 108 0.1
113.9 14.4 113.2 13.7 110.2 10.7 108 8.5 108 8.5 108 8.5
100.3 17.9 99.4 17 110 27.6 101.2 18.8 101.3 18.9 101.1 18.7
137.2 0.3 137.5 0 123.8 13.7 131.2 6.3 131 6.5 131.2 6.3
129.1 1.9 129.3 1.7 123.4 7.6 126.2 4.8 126 5 126.2 4.8
129.4 10.1 129.2 9.9 123.4 4.1 126.2 6.9 126.2 6.9 126.1 6.8
125.5 2.5 125.6 2.4 123.3 4.7 124 4 123.8 4.2 124 4
125.9 9.7 125.5 9.3 123.3 7.1 124 7.8 124.1 7.9 123.9 7.7
119 6.1 118.7 5.8 123 10.1 119.8 6.9 119.8 6.9 119.8 6.9
113.8 0.7 113.8 0.7 122.9 9.8 116.8 3.7 116.6 3.5 116.8 3.7
114.3 12 113.7 11.4 122.9 20.6 116.8 14.5 116.9 14.6 116.7 14.4
152.4 4.6 152.7 4.3 137.8 19.2 149.3 7.8 149.1 7.9 149.3 7.7
145.8 6.1 146.2 5.7 137.3 14.6 144.5 7.4 144.3 7.6 144.5 7.4
146.1 6.1 146.1 6.1 137.3 2.7 144.5 4.5 144.5 4.5 144.5 4.5
141.4 11.6 141.8 11.2 137 16 141.3 11.7 141.1 11.9 141.4 11.6
141.5 6.5 141.8 6.2 137 11 141.3 6.7 141.2 6.8 141.3 6.7
141.9 6.9 141.7 6.7 137 2 141.3 6.3 141.4 6.4 141.3 6.3
137 9.5 137.2 9.3 136.8 9.7 138 8.5 137.9 8.6 138 8.5
138.2 6.2 138.3 6.3 136.8 4.8 138.8 6.8 138.8 6.8 138.8 6.8
132.2 10.8 132.6 10.4 136.6 6.4 134.6 8.4 134.4 8.6 134.7 8.3
132.6 11.9 132.9 11.6 136.6 7.9 134.8 9.7 134.7 9.8 134.9 9.6
132.7 11.2 132.5 11 136.6 15.1 134.6 13.1 134.7 13.2 134.6 13.1
132.9 1.4 132.8 1.5 136.6 2.3 134.8 0.5 134.8 0.5 134.8 0.5
133 3.5 132.8 3.3 136.6 7.1 134.8 5.3 135 5.5 134.8 5.3
126.5 10 126.7 9.8 136.3 0.2 130.4 6.1 130.2 6.3 130.4 6.1
127 4 126.6 3.6 136.3 13.3 130.4 7.4 130.5 7.5 130.3 7.3
121.6 1.2 121.5 1.1 136.1 15.7 126.6 6.2 126.6 6.2 126.6 6.2
121.8 3.4 121.5 3.1 136.1 17.7 126.6 8.2 126.7 8.3 126.6 8.2
168.3 8.1 168.7 7.7 152.6 23.8 167.2 9.2 167.1 9.3 167.2 9.2
163 7 163.4 6.6 152 18 162.7 7.3 162.6 7.4 162.8 7.2
163.2 2.8 163.4 3 152 8.4 162.7 2.3 162.7 2.3 162.7 2.3
158.8 14.5 159.3 14 151.6 21.7 159.2 14.1 159 14.3 159.3 14
158.9 5.1 159.3 4.7 151.6 12.4 159.2 4.8 159.1 4.9 159.3 4.7
159.2 2.2 159.2 2.2 151.6 5.4 159.2 2.2 159.4 2.4 159.2 2.2
157.2 11.8 157.6 11.4 151.5 17.5 157.8 11.2 157.7 11.3 157.9 11.1
157.7 1.7 157.5 1.5 151.5 4.5 157.8 1.8 158 2 157.8 1.8
157.2 6.2 157.4 6.4 151.4 0.4 157.6 6.6 157.6 6.6 157.7 6.7
150.5 5 150.4 4.9 150.9 5.4 151.8 6.3 152 6.5 151.8 6.3
152.1 9.1 152.1 9.1 151 8 153.2 10.2 153.3 10.3 153.2 10.2
152.2 6.8 152.5 6.5 151 8 153.5 5.5 153.4 5.6 153.6 5.4
152.5 4.5 152.4 4.4 151 3 153.5 5.5 153.6 5.6 153.5 5.5
144.8 1.8 144.6 1.6 150.6 7.6 146.9 3.9 147.1 4.1 146.9 3.9
144.2 11.1 144.2 11.1 150.4 17.3 146.6 13.5 146.6 13.5 146.6 13.5
142.2 2.2 142 2 150.3 10.3 144.8 4.8 144.9 4.9 144.7 4.7
138.9 3.1 138.6 3.4 150.2 8.2 141.9 0.1 142.1 0.1 141.8 0.2
137.6 2.1 137.5 2.2 150.1 10.4 140.9 1.2 141 1.3 140.9 1.2
135.3 3.7 135 4 150 11 138.9 0.1 139 0 138.9 0.1
126.3 4.2 126.2 4.3 149.5 19 131.4 0.9 131.4 0.9 131.4 0.9
150.3 0.7 150.4 0.6 150.9 0.1 151.8 0.8 151.8 0.8 151.8 0.8
184.8 10.4 185.2 10 168.4 26.8 185.1 10.1 184.9 10.3 185.1 10.1
180.4 8.2 180.9 7.7 167.7 20.9 180.9 7.7 180.7 7.9 181 7.6
180.6 0.6 180.8 0.8 167.7 12.3 180.9 0.9 180.9 0.9 180.9 0.9
177.1 2.1 177.1 2.1 167.2 7.8 177.4 2.4 177.5 2.5 177.3 2.3
(continued )
7
Model 1
(J þ MW)
Calc BP
No. Chemical name J¼F Fx ¼ Jx Fy ¼ Jy W G Gx Gy N R MW Exp BP ( C) ( C) Residual
55 4-Methyl-1-heptanol 2.95482 2.92152 2.96568 108 23.93404 23.66431 24.02201 9 0 130.23 188 174.9 13.1
56 4-Octanol 2.95482 2.90653 2.97057 108 23.93404 23.54289 24.06162 9 0 130.23 176.3 174.9 1.4
57 2-Ethyl-1-hexanol 3.09225 3.05202 3.10536 104 25.04723 24.72136 25.15342 9 0 130.23 184.6 171 13.6
58 2-Methyl-2-heptanol 3.07299 3.02701 3.08798 104 24.89122 24.51878 25.01264 9 0 130.23 156 171.5 15.5
59 2.5-Dimethyl-1-hexanol 3.06082 3.02369 3.07293 104 24.79264 24.49189 24.89073 9 0 130.23 179.5 171.8 7.7
60 5-Methyl-2-heptanol 3.06082 3.02059 3.07393 104 24.79264 24.46678 24.89883 9 0 130.23 172 171.8 0.2
61 6-Methyl-3-heptanol 3.06082 3.01484 3.07581 104 24.79264 24.4202 24.91406 9 0 130.23 174 171.8 2.2
63 3-Methyl-2-heptanol 3.15528 3.11139 3.16959 102 25.55777 25.20226 25.67368 9 0 130.23 166.1 169.2 3.1
64 2-Methyl-3-heptanol 3.15528 3.10443 3.17186 102 25.55777 25.14588 25.69207 9 0 130.23 167.5 169.2 1.7
65 2-Methyl-4-heptanol 3.15125 3.1004 3.16783 102 25.52513 25.11324 25.65942 9 0 130.23 164 169.3 5.3
66 5-Methyl-3-heptanol 3.22305 3.17476 3.23879 100 26.10671 25.71556 26.2342 9 0 130.23 172 167.2 4.8
67 3-Methyl-3-heptanol 3.33007 3.27638 3.34758 98 26.97357 26.53868 27.1154 9 0 130.23 163 164.2 1.2
68 4-Methyl-3-heptanol 3.32476 3.27391 3.34134 98 26.93056 26.51867 27.06485 9 0 130.23 170 164.3 5.7
69 3-Methyl-4-heptanol 3.32476 3.27106 3.34227 98 26.93056 26.49559 27.07239 9 0 130.23 162 164.3 2.3
72 4-Methyl-4-heptanol 3.43105 3.37416 3.4496 96 27.79151 27.3307 27.94176 9 0 130.23 161 161.3 0.3
73 2.4.4-Trimethyl-1-heptanol 3.69905 3.66539 3.71003 168 37.29875 36.95935 37.40947 11 0 158.28 168.5 190.3 21.8
74 3-Ethyl-3-hexanol 3.61739 3.5569 3.63711 92 29.30086 28.81089 29.46059 9 0 130.23 160.5 156 4.5
75 2.3-Dimethyl-2-hexanol 3.58873 3.53504 3.60624 92 29.06871 28.63382 29.21054 9 0 130.23 160 156.8 3.2
78 3-Ethyl-2-methyl-2-pentanol 3.79291 3.73602 3.81145 88 30.72257 30.26176 30.87275 9 0 130.23 156 151 5
79 2.4.4-Trimethyl-2-pentanol 3.74642 3.69272 3.76392 88 30.346 29.91103 30.48775 9 0 130.23 147.5 152.3 4.8
85 6-Methyl-2-heptanol 2.91466 2.87604 2.92725 108 23.60875 23.29592 23.71073 9 0 130.23 174 176 2
86 3-Methyl-1-heptanol 2.95482 2.92034 2.96607 108 23.93404 23.65475 24.02517 9 0 130.23 186 174.9 11.1
87 3-Ethyl-2-methyl-3-pentanol 3.91921 3.85461 3.94027 86 31.7456 31.22234 31.91619 9 0 130.23 158 147.4 10.6
89 1-Nonanol 2.6476 2.62071 2.65637 165 24.06909 23.82464 24.14882 10 0 144.26 213.3 201.9 11.4
90 7-Methyl-1-octanol 2.77319 2.74562 2.78218 158 25.21082 24.96018 25.29255 10 0 144.26 206 198.3 7.7
91 2-Nonanol 2.77319 2.74069 2.78378 158 25.21082 24.91536 25.30709 10 0 144.26 198.5 198.3 0.2
92 3-Nonanol 2.88616 2.84796 2.89862 153 26.23782 25.89055 26.35109 10 0 144.26 195 195.1 0.1
93 4-Nonanol 2.96802 2.9253 2.98194 150 26.982 26.59364 27.10855 10 0 144.26 192.5 192.8 0.3
94 5-Nonanol 2.99842 2.95395 3.01292 149 27.25836 26.85409 27.39018 10 0 144.26 193 191.9 1.1
95 2-Methyl-2-octanol 3.04376 3.00416 3.05667 146 27.67055 27.31055 27.78791 10 0 144.26 178 190.6 12.6
96 2.6-Dimethyl-2-heptanol 3.20546 3.16436 3.21885 139 29.14055 28.76691 29.26227 10 0 144.26 173 186.1 13.1
98 2.6-Dimethyl-4-heptanol 3.33743 3.28898 3.35323 135 30.34027 29.89982 30.48391 10 0 144.26 174.5 182.3 7.8
100 2.2.3-Trimethyl-3-hexanol 4.10178 4.0427 4.12104 115 37.28891 36.75182 37.464 10 0 144.26 156 160.6 4.6
104 2-Methyl-3-ethyl-3-heptanol 3.88494 3.83208 3.90217 162 39.17315 38.64014 39.34688 11 0 158.28 177.5 185 7.5
105 2-Methyl-3-ethyl-1-heptanol 3.55688 3.52225 3.56816 174 35.86521 35.51602 35.97895 11 0 158.28 193 194.4 1.4
106 5-Methyl-3-ethyl-3-heptanol 3.85671 3.80608 3.87321 162 38.88849 38.37797 39.05487 11 0 158.28 172 185.9 13.9
107 2.4.4-Trimethyl-3-hexanol 4.03412 3.97812 4.05237 116 36.67382 36.16473 36.83973 10 0 144.26 170 162.5 7.5
108 3.4.4-Trimethyl-3-hexanol 4.28176 4.22268 4.30102 111 38.92509 38.388 39.10018 10 0 144.26 165.5 155.4 10.1
8


174.5 13.5 175 13 167 21 175.2 12.8 175 13 175.3 12.7

174.9 1.4 174.8 1.5 167 9.3 175.2 1.1 175.4 0.9 175.2 1.1
170.7 13.9 171 13.6 166.5 18.1 171.5 13.1 171.4 13.2 171.5 13.1
171.5 15.5 171.5 15.5 166.5 10.5 172 16 172.1 16.1 172 16
171.6 7.9 171.9 7.6 166.5 13 172.3 7.2 172.1 7.4 172.4 7.1
171.7 0.3 171.9 0.1 166.5 5.5 172.3 0.3 172.2 0.2 172.3 0.3
171.8 2.2 171.9 2.1 166.5 7.5 172.3 1.7 172.4 1.6 172.3 1.7
168.9 13.6 169.4 13.1 166.3 16.2 169.8 12.7 169.6 12.9 169.9 12.6
169 2.9 169.2 3.1 166.3 0.2 169.7 3.6 169.7 3.6 169.7 3.6
169.2 1.7 169.1 1.6 166.3 1.2 169.7 2.2 169.9 2.4 169.7 2.2
169.4 5.4 169.2 5.2 166.3 2.3 169.8 5.8 170 6 169.8 5.8
167.2 4.8 167.2 4.8 166 6 167.9 4.1 167.9 4.1 167.9 4.1
164.3 1.3 164.2 1.2 165.8 2.8 165 2 165.1 2.1 164.9 1.9
164.4 5.6 164.3 5.7 165.8 4.2 165.1 4.9 165.2 4.8 165.1 4.9
164.4 2.4 164.3 2.3 165.8 3.8 165.1 3.1 165.2 3.2 165 3
157 8.5 157.2 8.3 165.1 0.4 158.2 7.3 158.1 7.4 158.3 7.2
165.6 11.2 165.6 11.2 165.8 11.4 166.3 11.9 166.3 11.9 166.3 11.9
161.5 0.5 161.3 0.3 165.5 4.5 162.2 1.2 162.4 1.4 162.1 1.1
190 21.5 190.4 21.9 197.2 28.7 186.2 17.7 185.8 17.3 186.4 17.9
156.2 4.3 156 4.5 165.1 4.6 157.1 3.4 157.3 3.2 157 3.5
156.8 3.2 156.8 3.2 165.1 5.1 157.9 2.1 157.9 2.1 157.9 2.1
157.3 0.7 157.1 0.9 165.1 7.1 158.2 0.2 158.3 0.3 158.2 0.2
153.8 4.3 153.6 4.5 164.8 6.7 154.8 3.3 154.9 3.2 154.7 3.4
151 5 151 5 164.6 8.6 152.3 3.7 152.3 3.7 152.3 3.7
152.3 4.8 152.4 4.9 164.6 17.1 153.6 6.1 153.5 6 153.6 6.1
148.7 1.8 148.6 1.9 164.3 13.8 150 0.5 150 0.5 150 0.5
156.9 0.9 156.8 0.8 165.1 9.1 157.9 1.9 158 2 157.8 1.8
162.9 5.4 162.8 5.3 165.5 8 163.7 6.2 163.8 6.3 163.6 6.1
150.8 9.6 150.8 9.6 164.6 4.2 152 8.4 152 8.4 152 8.4
157 8.5 157.2 8.3 165.1 0.4 158.2 7.3 158.1 7.4 158.3 7.2
175.8 1.8 176.1 2.1 167 7 176.3 2.3 176.3 2.3 176.3 2.3
174.5 11.5 175 11 167 19 175.2 10.8 175 11 175.3 10.7
147.6 10.4 147.4 10.6 164.3 6.3 148.8 9.2 149 9 148.8 9.2
144.9 11.6 144.7 11.8 164.1 7.6 146.2 10.3 146.3 10.2 146.2 10.3
201.6 11.7 202 11.3 185.3 28 202.8 10.5 202.7 10.6 202.9 10.4
198 8 198.4 7.6 184.5 21.5 199 7 198.8 7.2 199 7
198.2 0.3 198.4 0.1 184.5 14 199 0.5 199 0.5 199 0.5
195.1 0.1 195.1 0.1 183.9 11.1 195.5 0.5 195.6 0.6 195.5 0.5
192.9 0.4 192.8 0.3 183.5 9 193 0.5 193.2 0.7 192.9 0.4
192 1 191.9 1.1 183.4 9.6 192.1 0.9 192.3 0.7 192 1
190.6 12.6 190.7 12.7 183 5 190.7 12.7 190.7 12.7 190.7 12.7
186 13 186.1 13.1 182.2 9.2 185.7 12.7 185.7 12.7 185.7 12.7
183.4 8.4 183.3 8.3 181.8 6.8 182.8 7.8 182.9 7.9 182.7 7.7
182.4 7.9 182.3 7.8 181.7 7.2 181.7 7.2 181.8 7.3 181.6 7.1
178.7 5.7 178.7 5.7 181.2 8.2 177.8 4.8 177.8 4.8 177.7 4.7
160.7 4.7 160.5 4.5 179.3 23.3 158.2 2.2 158.2 2.2 158.2 2.2
172.5 1.5 172.4 1.4 180.5 9.5 171 0 171.1 0.1 171 0
174 1 173.8 0.8 180.7 7.7 172.6 0.4 172.7 0.3 172.5 0.5
174.2 3.2 174.1 3.1 180.7 9.7 172.8 1.8 172.9 1.9 172.8 1.8
185.2 7.7 185 7.5 196.4 18.9 179.9 2.4 180 2.5 179.9 2.4
194.1 1.1 194.5 1.5 197.9 4.9 191.1 1.9 190.8 2.2 191.2 1.8
186 14 185.8 13.8 196.4 24.4 180.9 8.9 180.9 8.9 180.9 8.9
162.5 7.5 162.5 7.5 179.4 9.4 160.3 9.7 160.2 9.8 160.3 9.7
155.5 10 155.4 10.1 178.8 13.3 152.7 12.8 152.6 12.9 152.7 12.8
(continued )
9
Model 1
(J þ MW)
No. Chemical name J¼F Fx ¼ Jx Fy ¼ Jy W G Gx Gy N R MW Exp BP ( C) Calc BP ( C) Residual
109 4-Methyl-4-octanol 3.41751 3.36679 3.43405 134 31.06827 30.60718 31.21864 10 0 144.26 180 180 0
110 4-Ethyl-4-heptanol 3.69029 3.63429 3.70855 126 33.54809 33.039 33.71409 10 0 144.26 182 172.3 9.7
111 2-Methyl-2-octanol 3.04376 3.00416 3.05667 146 27.67055 27.31055 27.78791 10 0 144.26 178 190.6 12.6
112 1-Decanol 2.69092 2.66667 2.69882 220 27.13344 26.88892 27.2131 11 0 158.28 231.1 219 12.1
113 8-Methyl-1-nonanol 2.79642 2.77169 2.80449 212 28.19724 27.94787 28.27861 11 0 158.28 219.9 216 3.9
114 2-Decanol 2.79642 2.76757 2.80583 212 28.19724 27.90633 28.29212 11 0 158.28 211 216 5
115 4-Decanol 2.97258 2.9347 2.98493 202 29.97352 29.59156 30.09804 11 0 158.28 210.5 211 0.5
116 3.7-Dimethyl-1-octanol 3.09962 3.07144 3.10881 194 31.2545 30.97035 31.34717 11 0 158.28 212.5 207.4 5.1
117 2.7-Dimethyl-3-octanol 3.24187 3.20145 3.25504 186 32.68886 32.28129 32.82165 11 0 158.28 193.5 203.3 9.8
118 2.6-Dimethyl-4-octanol 3.42853 3.38359 3.44318 178 34.57101 34.11787 34.71873 11 0 158.28 195 198 3
119 2.3-Dimethyl-3-octanol 3.55135 3.50466 3.56657 174 35.80945 35.33866 35.96291 11 0 158.28 189 194.5 5.5
120 5-Methyl-5-nonanol 3.43403 3.38734 3.44925 180 34.62647 34.15568 34.77994 11 0 158.28 202 197.9 4.1
121 4-Methyl-1-nonanol 3.01712 2.99019 3.0259 200 30.42263 30.15108 30.51116 11 0 158.28 216 209.7 6.3
122 2-Methyl-3-nonanol 3.10483 3.06572 3.11758 194 31.30704 30.91268 31.4356 11 0 158.28 200 207.2 7.2
123 2.2.5.5-Tetramethyl-3-hexanol 3.98668 3.93606 4.00319 156 40.19902 39.68861 40.3655 11 0 158.28 170 182.2 12.2
124 4-Propyl-4-heptanol 3.79023 3.73737 3.80746 166 38.21815 37.68515 38.39189 11 0 158.28 191 187.7 3.3
125 2.4.6-Trimethyl-4-heptanol 3.79381 3.74318 3.81032 164 38.25425 37.74373 38.42073 11 0 158.28 181 187.6 6.6
126 3-Ethyl-3-octanol 3.5109 3.46422 3.52613 176 35.40158 34.93089 35.55514 11 0 158.28 199 195.7 3.3
127 3-Ethyl-2-methyl-3-heptanol 3.88494 3.83208 3.90217 162 39.17315 38.64014 39.34688 11 0 158.28 193 185 8
128 1-Undecanol 2.72724 2.70518 2.73444 286 30.20943 29.96507 30.28918 12 0 172.31 245 236.3 8.7
129 2-Undecanol 2.81702 2.7911 2.82547 277 31.20391 30.9168 31.29751 12 0 172.31 228 233.7 5.7
130 3-Undecanol 2.90185 2.87186 2.91163 270 32.14357 31.81137 32.2519 12 0 172.31 229 231.3 2.3
131 5-Undecanol 3.02388 2.98729 3.0358 262 33.49529 33.08998 33.62732 12 0 172.31 229 227.9 1.1
132 6-Undecanol 3.04176 3.00414 3.05402 261 33.69334 33.27663 33.82914 12 0 172.31 228 227.3 0.7
133 1-Dodecanol 2.75815 2.73791 2.76475 364 33.29481 33.05049 33.37448 13 0 186.34 261.9 253.7 8.2
134 2-Dodecanol 2.83541 2.8119 2.84307 354 34.22745 33.94365 34.31992 13 0 186.34 246 251.5 5.5
135 1-Tridecanol 2.78477 2.76607 2.79086 455 36.38766 36.14331 36.46724 14 0 200.36 276 271.3 4.7
136 1-Tetradecanol 2.80793 2.79056 2.81359 560 39.48652 39.24225 39.56611 15 0 214.39 289 289 0
137 1-Pentadecanol 2.82826 2.81205 2.83355 680 42.59027 42.34616 42.66993 16 0 228.42 304.9 306.7 1.8
138 1-Hexadecanol 2.84626 2.83105 2.85122 816 45.69829 45.45408 45.77792 17 0 242.44 312 324.5 12.5
10


180.1 0.1 180 0 181.6 1.6 179.2 0.8 179.4 0.6 179.2 0.8
172.4 9.6 172.2 9.8 180.6 1.4 170.8 11.2 171 11 170.8 11.2
190.6 12.6 190.7 12.7 183 5 190.7 12.7 190.7 12.7 190.7 12.7
218.8 12.3 219.1 12 203.4 27.7 220.6 10.5 220.5 10.6 220.6 10.5
215.8 4.1 216.1 3.8 202.5 17.4 217 2.9 216.8 3.1 217 2.9
215.9 4.9 216 5 202.5 8.5 217 6 217 6 217 6
211.1 0.6 211 0.5 201.3 9.2 211 0.5 211.2 0.7 210.9 0.4
207.1 5.4 207.5 5 200.3 12.2 206.7 5.8 206.4 6.1 206.7 5.8
203.4 9.9 203.3 9.8 199.3 5.8 201.8 8.3 201.9 8.4 201.8 8.3
198.1 3.1 198 3 198.4 3.4 195.5 0.5 195.6 0.6 195.4 0.4
194.6 5.6 194.5 5.5 197.9 8.9 191.3 2.3 191.4 2.4 191.3 2.3
198 4 197.8 4.2 198.6 3.4 195.3 6.7 195.4 6.6 195.2 6.8
209.5 6.5 209.8 6.2 201 15 209.5 6.5 209.2 6.8 209.5 6.5
207.3 7.3 207.2 7.2 200.3 0.3 206.5 6.5 206.6 6.6 206.4 6.4
182.2 12.2 182.1 12.1 195.7 25.7 176.5 6.5 176.4 6.4 176.5 6.5
187.9 3.1 187.7 3.3 196.9 5.9 183.1 7.9 183.3 7.7 183.1 7.9
187.8 6.8 187.6 6.6 196.7 15.7 183 2 183.1 2.1 183 2
195.8 3.2 195.6 3.4 198.1 0.9 192.7 6.3 192.8 6.2 192.6 6.4
185.2 7.8 185 8 196.4 3.4 179.9 13.1 180 13 179.9 13.1
236.1 8.9 236.3 8.7 222.9 22.1 238.3 6.7 238.2 6.8 238.3 6.7
233.7 5.7 233.8 5.8 221.8 6.2 234.9 6.9 234.9 6.9 234.9 6.9
231.3 2.3 231.3 2.3 220.9 8.1 231.7 2.7 231.8 2.8 231.7 2.7
228 1 227.8 1.2 220 9 227.2 1.8 227.4 1.6 227.1 1.9
227.5 0.5 227.3 0.7 219.8 8.2 226.5 1.5 226.8 1.2 226.4 1.6
253.7 8.2 253.8 8.1 243.7 18.2 255.9 6 255.8 6.1 256 5.9
251.5 5.5 251.5 5.5 242.5 3.5 252.8 6.8 252.8 6.8 252.8 6.8
271.3 4.7 271.3 4.7 266.2 9.8 273.6 2.4 273.5 2.5 273.6 2.4
289.1 0.1 288.9 0.1 290.3 1.3 291.2 2.2 291.1 2.1 291.2 2.2
306.9 2 306.6 1.7 316.2 11.3 308.8 3.9 308.7 3.8 308.8 3.9
324.9 12.9 324.4 12.4 344.1 32.1 326.4 14.4 326.3 14.3 326.4 14.4
11
Table 6A. Aqueous solubility of alcohols.
Model 1
(J þ MW)
Calc
No. Chemical name J¼F Fx ¼ Jx Fy ¼ Jy W G Gx Gy N R MW Exp log (1/S) log (1/S) Residual
1 Ethanol 1.63299 1.53344 1.66545 4 3.67423 3.45024 3.74726 3 0 46.07 1.1 1.01 0.1
2 1-Propanol 1.97474 1.90008 1.99909 10 6.31917 6.08026 6.39709 4 0 60.1 0.62 0.57 0.1
3 1-Butanol 2.19061 2.13232 2.20961 20 9.12754 8.88467 9.20671 5 0 74.12 0.03 0.06 0
4 2-Methyl-1-propanol 2.53954 2.47317 2.56118 18 10.58142 10.30488 10.67158 5 0 74.12 0.1 0.25 0.1
5 2-Butanol 2.53954 2.46242 2.56468 18 10.58142 10.26008 10.68617 5 0 74.12 0.47 0.25 0.2
6 1-Pentanol 2.33909 2.29163 2.35457 35 12.02961 11.78553 12.10922 6 0 88.15 0.59 0.49 0.1
7 3-Methyl-butanol 2.62721 2.57569 2.64401 32 13.51137 13.24641 13.59777 6 0 88.15 0.51 0.33 0.2
8 2-Pentanol 2.62721 2.56499 2.6475 32 13.51137 13.19138 13.61571 6 0 88.15 0.28 0.33 0.1
9 2-Methyl-1-butanol 2.75418 2.69782 2.77256 31 14.16435 13.8745 14.25888 6 0 88.15 0.46 0.26 0.2
10 3-Pentanol 2.75418 2.68471 2.77683 31 14.16435 13.80708 14.28084 6 0 88.15 0.21 0.26 0.1
11 3-Methyl-2-butanol 2.9935 2.92402 3.01615 29 15.39514 15.03782 15.51163 6 0 88.15 0.18 0.13 0
12 2-Methyl-2-butanol 3.16849 3.08979 3.19415 28 16.29509 15.89035 16.42706 6 0 88.15 0.15 0.04 0.2
13 1-Hexanol 2.44747 2.40756 2.46048 56 14.99075 14.74631 15.07044 7 0 102.18 1.21 1.06 0.1
14 4-Methyl-1-pentanol 2.67826 2.63602 2.69203 52 16.40434 16.14562 16.48868 7 0 102.18 1.14 0.94 0.2
15 2-Hexanol 2.67826 2.62704 2.69496 52 16.40434 16.09062 16.50663 7 0 102.18 0.87 0.94 0.1
16 2-Methyl-1-pentanol 2.83182 2.784 2.84741 50 17.3449 17.052 17.44039 7 0 102.18 1.11 0.85 0.3
17 3-Hexanol 2.83182 2.77209 2.85129 50 17.3449 16.97905 17.46415 7 0 102.18 0.8 0.85 0.1
18 2-Ethyl-1-butanol 2.9923 2.94108 3.009 48 18.32784 18.01412 18.43013 7 0 102.18 1.01 0.76 0.2
19 4-Methyl-pentanol 2.67826 2.63602 2.69203 52 16.40434 16.14562 16.48868 7 0 102.18 0.79 0.94 0.1
22 2-Methyl-2-pentanol 3.15449 3.08932 3.17574 46 19.32125 18.92209 19.45141 7 0 102.18 0.49 0.67 0.2
23 3-Methyl-2-pentanol 3.14421 3.08448 3.16368 46 19.25829 18.89244 19.37754 7 0 102.18 0.71 0.68 0
24 2-Methyl-3-pentanol 3.14421 3.07903 3.16546 46 19.25829 18.85906 19.38844 7 0 102.18 0.7 0.68 0
26 3-Methyl-3-pentanol 3.36044 3.2887 3.38382 44 20.5827 20.14329 20.7259 7 0 102.18 0.36 0.56 0.2
29 1-Heptanol 2.53006 2.49567 2.54127 84 17.99154 17.74699 18.07125 8 0 116.2 1.81 1.65 0.2
30 2-Heptanol 2.71584 2.67268 2.72991 79 19.31264 19.00572 19.41269 8 0 116.2 1.55 1.54 0
31 3-Heptanol 2.86207 2.81106 2.87869 76 20.3525 19.98976 20.47068 8 0 116.2 1.44 1.46 0
32 4-Heptanol 2.91961 2.86531 2.93732 75 20.76167 20.37554 20.88761 8 0 116.2 1.4 1.43 0
33 5-Methyl-2-hexanol 2.92782 2.88233 2.94265 74 20.82005 20.49657 20.92551 8 0 116.2 1.38 1.43 0
34 2-Methyl-3-hexanol 3.17082 3.11275 3.18975 70 22.54805 22.13511 22.68267 8 0 116.2 1.32 1.29 0
35 2-Methyl-2-hexanol 3.11177 3.05746 3.12947 71 22.12814 21.74194 22.25401 8 0 116.2 1.07 1.33 0.3
39 3-Methyl-3-hexanol 3.37338 3.31097 3.39373 67 23.98848 23.54468 24.13319 8 0 116.2 0.98 1.18 0.2
42 3-Ethyl-3-pentanol 3.58321 3.51574 3.60521 64 25.4806 25.00082 25.63705 8 0 116.2 0.83 1.07 0.2
44 2.3-Dimethyl-3-pentanol 3.70832 3.64085 3.73032 62 26.37028 25.89049 26.52672 8 0 116.2 0.84 1 0.2
48 1-Octanol 2.59508 2.56489 2.60492 120 21.02015 20.77561 21.09985 9 0 130.23 2.35 2.24 0.1
49 2-Octanol 2.74669 2.70956 2.7588 114 22.24819 21.94744 22.34628 9 0 130.23 2.09 2.16 0.1
50 2-Ethyl-1-hexanol 3.09225 3.05202 3.10536 104 25.04723 24.72136 25.15342 9 0 130.23 2.11 1.97 0.1
12

Calc Calc Calc Calc Calc Calc

log (1/S) Residual log (1/S) Residual log (1/S) Residual log (1/S) Residual log (1/S) Residual log (1/S) Residual
0.57 0.1 0.57 0.1 0.6 0 0.74 0.1 0.75 0.1 0.74 0.1
0.06 0 0.05 0 0.17 0.1 0.13 0.1 0.13 0.1 0.13 0.1
0.25 0.1 0.25 0.1 0.18 0.1 0.25 0.1 0.25 0.1 0.25 0.1
0.24 0.2 0.25 0.2 0.18 0.3 0.25 0.2 0.25 0.2 0.25 0.2
0.48 0.1 0.49 0.1 0.3 0.3 0.47 0.1 0.47 0.1 0.47 0.1
0.33 0.2 0.34 0.2 0.28 0.2 0.36 0.2 0.35 0.2 0.36 0.2
0.33 0.1 0.33 0.1 0.28 0 0.36 0.1 0.36 0.1 0.35 0.1
0.26 0.2 0.27 0.2 0.27 0.2 0.3 0.2 0.3 0.2 0.3 0.2
0.27 0.1 0.26 0.1 0.27 0.1 0.3 0.1 0.31 0.1 0.3 0.1
0.14 0 0.13 0 0.26 0.1 0.21 0 0.21 0 0.21 0
0.04 0.2 0.04 0.2 0.25 0.4 0.14 0.3 0.14 0.3 0.13 0.3
1.05 0.2 1.06 0.1 0.81 0.4 1.07 0.1 1.07 0.1 1.07 0.1
0.93 0.2 0.94 0.2 0.78 0.4 0.96 0.2 0.96 0.2 0.96 0.2
0.93 0.1 0.94 0.1 0.78 0.1 0.96 0.1 0.96 0.1 0.96 0.1
0.85 0.3 0.85 0.3 0.77 0.3 0.89 0.2 0.88 0.2 0.89 0.2
0.85 0.1 0.85 0.1 0.77 0 0.89 0.1 0.89 0.1 0.88 0.1
0.76 0.3 0.76 0.2 0.75 0.3 0.81 0.2 0.81 0.2 0.81 0.2
0.93 0.1 0.94 0.1 0.78 0 0.96 0.2 0.96 0.2 0.96 0.2
0.67 0.2 0.68 0.2 0.74 0.2 0.73 0.2 0.73 0.2 0.73 0.2
0.68 0.3 0.68 0.3 0.74 0.4 0.74 0.4 0.73 0.4 0.74 0.4
0.68 0.2 0.67 0.2 0.74 0.2 0.73 0.2 0.73 0.2 0.73 0.2
0.68 0 0.68 0 0.74 0 0.74 0 0.74 0 0.73 0
0.68 0 0.68 0 0.74 0 0.74 0 0.74 0 0.73 0
0.56 0.4 0.56 0.3 0.72 0.2 0.63 0.3 0.63 0.3 0.63 0.3
0.57 0.2 0.56 0.2 0.72 0.4 0.63 0.3 0.64 0.3 0.63 0.3
0.46 0.1 0.46 0.1 0.71 0.1 0.54 0.1 0.54 0.1 0.54 0.1
0.47 0.1 0.46 0.1 0.71 0.3 0.54 0.2 0.55 0.2 0.54 0.2
1.64 0.2 1.65 0.2 1.37 0.4 1.67 0.1 1.66 0.1 1.67 0.1
1.54 0 1.54 0 1.33 0.2 1.56 0 1.56 0 1.56 0
1.46 0 1.46 0 1.31 0.1 1.48 0 1.48 0 1.48 0
1.43 0 1.43 0 1.3 0.1 1.45 0 1.45 0.1 1.45 0
1.42 0 1.43 0 1.3 0.1 1.44 0.1 1.44 0.1 1.44 0.1
1.3 0 1.29 0 1.27 0.1 1.31 0 1.31 0 1.31 0
1.33 0.3 1.33 0.3 1.28 0.2 1.34 0.3 1.34 0.3 1.34 0.3
1.18 0.3 1.18 0.3 1.25 0.3 1.19 0.3 1.19 0.3 1.2 0.3
1.32 0.2 1.33 0.2 1.28 0.3 1.34 0.2 1.34 0.2 1.34 0.2
1.33 0.3 1.34 0.3 1.28 0.3 1.35 0.3 1.35 0.3 1.35 0.3
1.19 0.2 1.18 0.2 1.25 0.3 1.19 0.2 1.2 0.2 1.19 0.2
1.18 0.2 1.17 0.2 1.24 0.3 1.19 0.3 1.19 0.3 1.19 0.3
1.14 0.1 1.13 0.1 1.23 0 1.14 0.1 1.15 0.1 1.14 0.1
1.08 0.2 1.07 0.2 1.23 0.4 1.08 0.2 1.08 0.3 1.08 0.2
1.05 0.2 1.05 0.2 1.22 0.3 1.05 0.2 1.06 0.2 1.05 0.2
1.01 0.2 1 0.2 1.21 0.4 1.01 0.2 1.01 0.2 1.01 0.2
1.05 0.1 1.05 0.1 1.22 0.1 1.05 0.1 1.06 0.1 1.05 0.1
0.83 0.4 0.83 0.4 1.18 0.1 0.83 0.4 0.83 0.4 0.83 0.4
0.83 0.1 0.83 0.1 1.18 0.5 0.83 0.1 0.83 0.1 0.83 0.1
2.23 0.1 2.24 0.1 1.98 0.4 2.26 0.1 2.26 0.1 2.26 0.1
2.15 0.1 2.16 0.1 1.94 0.2 2.16 0.1 2.16 0.1 2.16 0.1
1.96 0.1 1.97 0.1 1.87 0.2 1.94 0.2 1.94 0.2 1.94 0.2
1.98 0.3 1.98 0.3 1.87 0.1 1.96 0.2 1.96 0.2 1.96 0.2
(continued )
13
Model 1
(J þ MW)
Calc
No. Chemical name J¼F Fx ¼ Jx Fy ¼ Jy W G Gx Gy N R MW Exp log (1/S) log (1/S) Residual
51 2-Methyl-2-heptanol 3.07299 3.02701 3.08798 104 24.89122 24.51878 25.01264 9 0 130.23 1.72 1.98 0.3
52 3-Methyl-3-heptanol 3.33007 3.27638 3.34758 98 26.97357 26.53868 27.1154 9 0 130.23 1.6 1.84 0.2
53 1-Nonanol 2.6476 2.62071 2.65637 165 24.06909 23.82464 24.14882 10 0 144.26 3.01 2.84 0.2
54 7-Methyl-1-octanol 2.77319 2.74562 2.78218 158 25.21082 24.96018 25.29255 10 0 144.26 2.49 2.77 0.3
55 2-Nonanol 2.77319 2.74069 2.78378 158 25.21082 24.91536 25.30709 10 0 144.26 2.74 2.77 0
56 3-Nonanol 2.88616 2.84796 2.89862 153 26.23782 25.89055 26.35109 10 0 144.26 2.66 2.71 0
57 4-Nonanol 2.96802 2.9253 2.98194 150 26.982 26.59364 27.10855 10 0 144.26 2.59 2.66 0.1
58 5-Nonanol 2.99842 2.95395 3.01292 149 27.25836 26.85409 27.39018 10 0 144.26 2.49 2.65 0.2
61 2.2-Diethyl-1-pentanol 3.87477 3.83031 3.88927 121 35.22518 34.821 35.357 10 0 144.26 2.42 2.17 0.3
62 1-Decanol 2.69092 2.66667 2.69882 220 27.13344 26.88892 27.2131 11 0 158.28 3.63 3.45 0.2
63 1-Dodecanol 2.75815 2.73791 2.76475 364 33.29481 33.05049 33.37448 13 0 186.34 4.67 4.67 0
Table 7A. Alcohol tomato toxicity.
Chemical
name Comp. No. SMILES J¼F Jx ¼ Fx Jy ¼ Fy W G Gx Gy DN2S4 N R MW totop
a
Methanol 1 1 CO 1 0.87807 1.03975 1 1.33333 1.17076 1.38633 2 0 32.042 6.55902
Ethanol 2 2 CCO 1.63299 1.53344 1.66545 4 3.67423 3.45024 3.74726 9.7 3 0 46.069 9.3835
1-Propanol 3 3 CCCO 1.97474 1.90008 1.99909 10 6.31917 6.08026 6.39709 14.10589 4 0 60.096 12.25427
2-Propanol 4 4 CC(O)C 2.32379 2.22934 2.35458 9 7.43613 7.13389 7.53466 16.15582 4 0 60.096 12.54257
1-Butanol 5 5 CCCCO 2.19061 2.13232 2.20961 20 9.12754 8.88467 9.20671 18.455 5 0 74.122 15.19027
2-Methyl-1-propanol 6 7 CC(C)CO 2.53954 2.47317 2.56118 18 10.58142 10.30488 10.67158 20.81907 5 0 74.122 15.47081
2-Methyl-1-propanol 7 8 CCC(O)C 2.53954 2.46242 2.56468 18 10.58142 10.26008 10.68617 20.81907 5 0 74.122 15.63435
Tert-Butanol 8 9 CC(O)(C)C 3.02372 2.93155 3.05376 16 12.59883 12.21479 12.724 24.07026 5 0 74.122 16.05197
1-Pentanol 9 10 CCCCCO 2.33909 2.29163 2.35457 35 12.02961 11.78553 12.10922 22.7762 6 0 88.149 18.17723
3-Methy-1-butanol 10 11 CC(C)CCO 2.62721 2.57569 2.64401 32 13.51137 13.24641 13.59777 24.97647 6 0 88.149 18.47704
2-Pentanol 11 12 CCCC(O)C 2.62721 2.56499 2.6475 32 13.51137 13.19138 13.61571 24.97647 6 0 88.149 18.68218
2-Methyl-1-butanol 12 13 CCC(C)CO 2.75418 2.69782 2.77256 31 14.16435 13.8745 14.25888 26.01209 6 0 88.149 18.6323
3-Pentanol 13 14 CCC(O)CC 2.75418 2.68471 2.77683 31 14.16435 13.80708 14.28084 26.01209 6 0 88.149 18.83972
Tert-Pentanol 14 15 CCC(C)(O)C 3.16849 3.08979 3.19415 28 16.29509 15.89035 16.42706 29.19276 6 0 88.149 19.37234
a
DN2S(4) cannot be calculated for compounds with fewer than three non-hydrogen atoms.
14

Calc Calc Calc Calc Calc Calc

log (1/S) Residual log (1/S) Residual log (1/S) Residual log (1/S) Residual log (1/S) Residual log (1/S) Residual
1.98 0.3 1.98 0.3 1.87 0.1 1.96 0.2 1.96 0.2 1.96 0.2
1.84 0.2 1.84 0.2 1.83 0.2 1.79 0.2 1.8 0.2 1.79 0.2
2.84 0.2 2.84 0.2 2.65 0.4 2.85 0.2 2.85 0.2 2.86 0.2
2.77 0.3 2.77 0.3 2.61 0.1 2.76 0.3 2.76 0.3 2.77 0.3
2.77 0 2.77 0 2.61 0.1 2.76 0 2.76 0 2.76 0
2.71 0.1 2.71 0 2.57 0.1 2.68 0 2.68 0 2.68 0
2.67 0.1 2.66 0.1 2.55 0 2.62 0 2.63 0 2.62 0
2.65 0.2 2.65 0.2 2.54 0.1 2.6 0.1 2.61 0.1 2.6 0.1
2.47 0.3 2.46 0.3 2.45 0.3 2.36 0.2 2.36 0.2 2.36 0.2
2.28 0.2 2.27 0.2 2.38 0.1 2.11 0.4 2.11 0.4 2.11 0.4
2.17 0.3 2.17 0.3 2.35 0.1 1.97 0.4 1.97 0.5 1.98 0.4
3.44 0.2 3.45 0.2 3.4 0.2 3.44 0.2 3.44 0.2 3.45 0.2
4.67 0 4.67 0 5.13 0.5 4.62 0 4.62 0.1 4.63 0
Exp. Tox. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid.
2.6 2.67 0.07 2.68 0.08 2.67 0.07 2.66 0.06 2.52 0.08 2.52 0.08 2.53 0.15
2.76 2.9 0.14 2.9 0.14 2.9 0.14 2.89 0.13 2.93 0.17 2.93 0.17 2.93 0.03
3.33 3.22 0.11 3.21 0.12 3.22 0.11 3.17 0.16 3.3 0.03 3.3 0.03 3.3 0.08
3.18 3.1 0.08 3.1 0.08 3.1 0.08 3.15 0.03 3.19 0.01 3.19 0.01 3.18 0.08
3.69 3.58 0.11 3.58 0.11 3.58 0.11 3.49 0.2 3.66 0.03 3.66 0.03 3.66 0.08
3.57 3.46 0.11 3.46 0.11 3.46 0.11 3.47 0.1 3.51 0.06 3.51 0.06 3.51 0.04
3.46 3.46 0 3.46 0 3.46 0 3.47 0.01 3.51 0.05 3.51 0.05 3.51 0.04
3.41 3.3 0.11 3.31 0.1 3.3 0.11 3.44 0.03 3.3 0.11 3.3 0.11 3.3 0
4.05 3.97 0.08 3.96 0.09 3.97 0.08 3.88 0.17 4 0.05 4 0.05 4 0.04
3.95 3.87 0.08 3.87 0.08 3.87 0.08 3.84 0.11 3.85 0.1 3.84 0.11 3.85 0.02
3.77 3.87 0.1 3.87 0.1 3.87 0.1 3.84 0.07 3.85 0.08 3.85 0.08 3.85 0.02
3.77 3.83 0.06 3.83 0.06 3.83 0.06 3.83 0.06 3.78 0.01 3.78 0.01 3.78 0.04
3.69 3.83 0.14 3.83 0.14 3.83 0.14 3.83 0.14 3.78 0.09 3.79 0.1 3.78 0.04
3.51 3.69 0.18 3.69 0.18 3.69 0.18 3.79 0.28 3.56 0.05 3.56 0.05 3.56 0.13
15
Table 8A. Alcohol spider toxicity.
Chemical
name Comp. No. SMILES J¼F Jx ¼ Fx Jy ¼ Fy W G Gx Gy DN2S4 N R MW totop
Methanol 1 1 COa 1 0.87807 1.03975 1 1.33333 1.17076 1.38633 2 0 32.042 6.55902

Ethanol 2 2 CCO 1.63299 1.53344 1.66545 4 3.67423 3.45024 3.74726 9.7 3 0 46.069 9.3835
1-Propanol 3 3 CCCO 1.97474 1.90008 1.99909 10 6.31917 6.08026 6.39709 14.10589 4 0 60.096 12.25427
2-Propanol 4 4 CC(O)C 2.32379 2.22934 2.35458 9 7.43613 7.13389 7.53466 16.15582 4 0 60.096 12.54257
1-Butanol 5 5 CCCCO 2.19061 2.13232 2.20961 20 9.12754 8.88467 9.20671 18.455 5 0 74.122 15.19027
2-Methyl-1-propanol 6 7 CC(C)CO 2.53954 2.47317 2.56118 18 10.58142 10.30488 10.67158 20.81907 5 0 74.122 15.47081
2-Methyl-1-propanol 7 8 CCC(O)C 2.53954 2.46242 2.56468 18 10.58142 10.26008 10.68617 20.81907 5 0 74.122 15.63435
tert-Butanol 8 9 CC(O)(C)C 3.02372 2.93155 3.05376 16 12.59883 12.21479 12.724 24.07026 5 0 74.122 16.05197
1-Pentanol 9 10 CCCCCO 2.33909 2.29163 2.35457 35 12.02961 11.78553 12.10922 22.7762 6 0 88.149 18.17723
3-Methy-1-butanol 10 11 CC(C)CCO 2.62721 2.57569 2.64401 32 13.51137 13.24641 13.59777 24.97647 6 0 88.149 18.47704
2-Pentanol 11 12 CCCC(O)C 2.62721 2.56499 2.6475 32 13.51137 13.19138 13.61571 24.97647 6 0 88.149 18.68218
2-Methyl-1-butanol 12 13 CCC(C)CO 2.75418 2.69782 2.77256 31 14.16435 13.8745 14.25888 26.01209 6 0 88.149 18.6323
3-Pentanol 13 14 CCC(O)CC 2.75418 2.68471 2.77683 31 14.16435 13.80708 14.28084 26.01209 6 0 88.149 18.83972
tert-Pentanol 14 15 CCC(C)(O)C 3.16849 3.08979 3.19415 28 16.29509 15.89035 16.42706 29.19276 6 0 88.149 19.37234
a
DN2S(4) cannot be calculated for compounds with fewer than three non-hydrogen atoms.
16
Exp Tox Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid. Calc. Tox. Resid.
2.8 2.84 0.04 2.84 0.04 2.84 0.04 2.86 0.06 2.67 0.13 2.67 0.13 2.67 0.13
3 3.03 0.03 3.03 0.03 3.03 0.03 3.03 0.03 3.06 0.06 3.06 0.06 3.06 0.06
3.32 3.35 0.03 3.34 0.02 3.35 0.03 3.27 0.05 3.42 0.1 3.42 0.1 3.42 0.1
3.26 3.2 0.06 3.2 0.06 3.2 0.06 3.24 0.02 3.31 0.05 3.32 0.06 3.31 0.05
3.77 3.72 0.05 3.71 0.06 3.72 0.05 3.6 0.17 3.76 0.01 3.76 0.01 3.76 0.01
3.72 3.57 0.15 3.56 0.16 3.57 0.15 3.55 0.17 3.62 0.1 3.62 0.1 3.62 0.1
3.62 3.57 0.05 3.57 0.05 3.57 0.05 3.55 0.07 3.62 0 3.63 0.01 3.62 0
3.28 3.36 0.08 3.37 0.09 3.36 0.08 3.5 0.22 3.43 0.15 3.44 0.16 3.43 0.15
4.09 4.11 0.02 4.11 0.02 4.11 0.02 4.05 0.04 4.1 0.01 4.09 0 4.1 0.01
4.09 3.99 0.1 3.99 0.1 3.99 0.1 3.97 0.12 3.95 0.14 3.95 0.14 3.96 0.13
3.9 3.99 0.09 3.99 0.09 3.99 0.09 3.97 0.07 3.95 0.05 3.95 0.05 3.95 0.05
3.96 3.94 0.02 3.94 0.02 3.94 0.02 3.95 0.01 3.89 0.07 3.89 0.07 3.89 0.07
3.81 3.94 0.13 3.94 0.13 3.94 0.13 3.95 0.14 3.89 0.08 3.89 0.08 3.89 0.08
3.75 3.76 0.01 3.77 0.02 3.76 0.01 3.88 0.13 3.69 0.06 3.69 0.06 3.69 0.06

Complexity of Chemical Graphs in Terms of Size, Branching, and Cyclicity

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Complexity of Chemical Graphs in Terms of Size, Branching, and Cyclicity

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SAR and QSAR in Environmental Research

Vol. 17, No. 4, August 2006, 429–450

Complexity of chemical graphs in terms of size,

(Received 9 November 2005; in final form 1 June 2006)

Complexity is a fuzzy notion that has recently begun to be treated scientifically by

*Corresponding author. Email: balabana@tamug.edu

SAR and QSAR in Environmental Research

2. On cyclicity and centricity

3. Molecular descriptors that separate size, cyclicity, and branching

The index J is the distance-based average connectivity [18–21]. It is related to the

Table 1. Alkanes C7–C9 and their topological indices: W and J.

No. SMILES Code Alkane name Abbreviated name W J

1 CCCCCCC Heptane C7 56 2.4475

No. N R W J F G DN2S(4) TOTOP

1 4 0 10 1.97474 1.9747 6.3192 14.1059 7.6483

No. N R W J F G DN2S(4) TOTOP

55 6 2 25 2.21365 6.6410 26.5638 42.6333 25.5267

No. N R W J F G DN2S(4) TOTOP

19 8 0 68 3.29248 3.2925 23.4132 38.7162 20.7289

Table 3. LOVIs for non-equivalent carbons in hexane and heptane isomers.

Alkane DN2N2 DN2S S Smiles notation

C6 0.818 0.182 9 CCCCCC

Alkane DN2N2 DN2S S Smiles notation

2,4-MM-C5 0.827 0.173 11 CC(C)CC(C)C

4. Influence of structure on the TIs discussed here

DN2S(4) vs J for all C4-C6 DN2S(4) vs G for all C4-C6

DN2S(4) vs F for all C4-C6 TOTOP vs F for all C4-C6

indices lead to quasi-parallel lines in the corresponding diagram similarly to the

DN2S(4) vs G for alkanes C7-C9

DN2S(4) vs J = F for alkanes C7-C9 TOTOP vs J = F for alkanes C7-C9

the practically linear correlation between their corresponding LOVIs, evidenced by

5. Degeneracy of the TIs discussed here

DðWÞ>DðJÞ ¼ DðFÞ ¼ DðGÞ>DðDN2 Sð4ÞÞ DðTOTOPÞ

The ‘‘desirable’’ features of J (inherited by derived indices F and especially G) are

6. QSAR and QSPR

6.1 Normal boiling points of alkanes and cycloalkanes

Independent variables r2 r2c:v: s F

Independent variables r2 r2c:v: S F

6.2 Normal boiling points of alcohols

Independent variables r2 r2c:v: s F

6.3 Aqueous solubility of alcohols

6.4 Toxicity of alcohols

Independent variables r2 r2c:v: s F

Independent variables r2 r2c:v: s F

[31] A.T. Balaban, T.S. Balaban. J. Math. Chem., 8, 383 (1991).

Table 4A. Normal b.p. of hydrocarbons.

Comp. No. Chemical name SMILES Class J Jx Jy F Fx Fy W G Gx

Table 4A. Continued.

Calc Calc Calc Calc BP Calc Calc Calc

Table 4A. Continued.

Comp. No. Chemical name SMILES Class J Jx Jy F Fx Fy W G Gx

Table 4A. Continued.

Calc Calc Calc Calc BP Calc Calc Calc

Table 5A. Normal b.p. of alcohols.

No. Chemical name J¼F Fx ¼ Jx Fy ¼ Jy W G Gx Gy N R MW Exp BP ( C) Calc BP ( C) Residual

Table 5A. Continued.

Model 2 Model 3 Model 4 Model 5 Model 6 Model 7

Calc BP Calc BP Calc BP Calc Calc Calc

Table 5A. Continued.

Table 5A. Continued.

Model 2 Model 3 Model 4 Model 5 Model 6 Model 7

Calc BP Calc BP Calc BP Calc Calc Calc

174.5 13.5 175 13 167 21 175.2 12.8 175 13 175.3 12.7