1

CONTENTS
Relative Atomic Masses of the Elements 2
Units, Symbols and Constants
The International System of Units (SI) 4
Recommended Values of Physical Constants 7
Selected Spectroscopic Data
Infrared
Characteristic Wavenumbers of Absorptions of
Organic Functional Groups 8
Anions and Cations 11
Coordination Compounds 11
Nuclear Magnetic Resonance
Properties of Selected NMR-Active Nuclides 12
Chemical Shifts of Common Functional Groups
13
C nuclei 13
1
H nuclei attached to saturated linkages 14
1
H nuclei attached to unsaturated linkages 15
1
H nuclei attached to heteroatoms 15
Additivity Table for 1H Chemical Shifts of Methylene Groups 15
SpinSpin Coupling Constants: 1H1H 16
Ultraviolet and Visible
Absorption Maxima of Substituted Benzene Rings 17
WoodwardFieser Rules for the Prediction of max Values 18
Electronic Absorption Characteristics of Transition Metal Complexes 19
Spectrochemical and Trans-Effect Series 19
Mass Spectrometry
Common Fragmentations and Fragment Ions 20
Symbols and Abbreviations Commonly Encountered in Organic Chemistry 21
The Proteinogenic Amino Acids 22
Group Theory
Symmetry Point Group Flow Diagram 23
Character Tables 24
Physical Definitions and Formulae 27
Mathematical Definitions and Formulae 28
The Greek Alphabet 31
The Periodic Table 32
2

RELATIVE ATOMIC MASSES Ar(E) ('ATOMIC WEIGHTS')

OF THE ELEMENTS
(Scaled to Ar(12C) = 12)
The atomic weights of many elements are not invariant but depend on the origin and treatment of the
material. The footnote to this Table elaborates the types of variation to be expected for individual
elements. The values of Ar(E) given here apply to elements as they exist naturally on Earth.

1 Hydrogen H 1.00794 a,b,c 21 Scandium Sc 44.955910

2 Helium He 4.002602 a,c 22 Titanium Yi 47.88
3 Lithium Li 6.941 a,b,c 23 Vanadium V 50.9415
4 Beryllium Be 9.01218 24 Chromium Cr 51.9961
5 Boron B 10.811 a,b,c 25 Manganese Mn 54.93805
6 Carbon C 12.011 c 26 Iron Fe 55.847
7 Nitrogen N 14.00674 a,c 27 Cobalt Co 58.93320
8 Oxygen O 15.9994 a,c 28 Nickel Ni 58.69
9 Fluorine F 18.9984032 29 Copper Cu 63.546 c
10 Neon Ne 20.1797 a,b 30 Zinc Zn 65.39
11 Sodium Na 22.989768 31 Gallium Ga 69.723
12 Magnesium 24.3050 32 Germanium Ge 72.61
13 Aluminium Al 26.98154 33 Arsenic As 74.9216
14 Silicon Si 29.0855 c 34 Selenium Se 78.96
15 Phosphorus P 30.973762 35 Bromine Br 79.904
16 Sulfur S 32.066 c 36 Krypton Kr 83.80 a,b
17 Chlorine Cl 35.4527 37 Rubidium Rb 85.4678 a
18 Argon Ar 39.948 a,c 38 Strontium Sr 87.62 a,c
19 Potassium K 39.0983 39 Yttrium Y 88.90585
20 Calcium Ca 40.078 a 40 Zirconium Zr 91.224 a
J. Emsley. The Elements, 3rd Edition, OUP, 1998.
a Geologically exceptional specimens are known in which the element has an isotopic composition
outside the limits for normal material. The difference between the atomic weight of the element in
such specimens and that given in the Table may exceed considerably the implied uncertainty.
b Modified isotopic compositions may be found in commercially available material because it has
been subjected to an undisclosed or inadvertent isotopic separation. Substantial deviations in atomic
weight of the element from that given in the Table can occur.
c Range in isotopic composition of normal terrestrial material prevents a more precise Ar(E) being
given; tabulated Ar(E) value should be applicable to any normal material.
 3

41 Niobium Nb 92.90638 73 Tantalum Ta 180.9479

42 Molybdenum Mo 95.94 74 Tungsten W 183.85
43 Technetium* Tc 98.9062 e 75 Rhenium Re 186.207
44 Ruthenium Ru 101.07 a 76 Osmium Os 190.2 a
45 Rhodium Rh 102.90550 77 Iridium Ir 192.22
46 Palladium Pd 106.42 a 78 Platinum Pt 195.08
47 Silver Ag 107.8682 a 79 Gold Au 196.96654
48 Cadmium Cd 112.411 a 80 Mercury Hg 200.59
49 Indium In 114.82 81 Thallium Tl 204.3833
50 Tin Sn 118.710 82 Lead Pb 207.2 a,c
51 Antimony Sb 121.75 83 Bismuth Bi 208.9804
52 Tellurium Te 127.60 84 Polonium* Po 209 d
53 Iodine I 126.90447 a 85 Astatine* At 210 d
54 Xenon Xe 131.29 a,b 86 Radon* Rn 222 d
55 Caesium Cs 132.9054 87 Francium* Fr 223 d
56 Barium Ba 137.327 88 Radium Ra 226.0254 d
57 Lanthanum La 138.9055 a 89 Actinium* Ax 227 d
58 Cerium Ce 140.115 a 90 Thorium* Th 232.0381 a,c,e
59 Praseodymium Pr 140.90765 91 Protactinium* Pa 231.03588 e
60 Neodymium Nd 144.24 a 92 Uranium* U 238.0289 a,b,e
61 Promethium* Pm 145 d 93 Neptinium* Np 237.0482
62 Samarium Sm 150.36 a 94 Plutonium* Pu 244 d
63 Europium Eu 151.965 a 95 Americium* Am 243 d
64 Gadolinium Gd 157.25 a 96 Curium* Cm 247 d
65 Terbium Tb 158.92534 97 Berkelium* Bk 247 d
66 Dysprosium Dy 162.50 a 98 Californium* Cf 251 d
67 Holmium Ho 164.93032 99 Eisteinium* Es 254 d
68 Erbium Er 167.26 a 100 Fermium* Fm 257 d
69 Thulium Tm 168.93421 101 Mendelevium* Md 258 d
70 Ytterbium Yb 173.04 a 102 Nobelium* No 259 d
71 Lutetium Lu 174.967 a 103 Lawrencium* Lr 260 d
72 Hafnium Hf 178.49

d Radioactive element that lacks a characteristic terrestrial isotopic composition.

e An element, without stable nuclide(s), exhibiting a range of characteristic terrestrial compositions of
long-lived radio-nuclide(s) such that a meaningful atomic weight can be given.
* Element has no stable nuclides.
4

UNITS and CONSTANTS

The International System of Units (SI)

Physical Quantity Name of Unit Symbol Expression in terms of

SI base units

SI base units

length metre m
mass kilogram kg
time second s
electric current ampere A
thermodynamic temperature kelvin K
amount of substance mole mol
SI derived units

energy, work, heat joule J m2 kg s2

force newton N m kg s2 = J m1
pressure, stress pascal Pa m1 kg s2 = N m2 = J m3
power watt W m2 kg s3 = J s1
electric charge coulomb C sA
electric potential volt V m2 kg s3 A1 = J A1 s1
electric resistance ohm m2 kg s3 A2 = V A1
electric conductance siemens S m2 kg1 s3 A2 = 1
electric capacitance farad F m2 kg1 s4 A2 = A s V1
magnetic flux weber Wb m2 kg s2 A1 = V s
inductance henry H m2 kg s2 A2 = V s A1
magnetic flux density tesla T kg s2 A1 = V s m2
frequency hertz Hz s1
/ (T/K 273.15)

Celsius temperature () degree Celsius C
plane angle radian rad
solid angle steradian sr
 5

SI Prefixes

Fraction Prefix Symbol Multiple Prefix Symbol

101 deci d 10 deca da

102 centi c 102 hecto h
3 3
10 milli m 10 kilo k

6 6
10 micro 10 mega M
109 nano n 109 giga G
1012 pico p 1012 tera T
1015 femto f 1015 peta P
1018 atto 1018 exa E

Decimal Fractions and Multiples of SI Units Having Special Names

Physical Quantity Name of Unit Symbol Definition

length ngstrm 1010 m = 101 nm = 100 pm

area barn b 1028 m2
volume litre l 1203 m3 = 1 dm3 = 1000 cm3
force dyne dyn 105 N
pressure bar bar 105 Pa
energy erg erg 107 J
kinematic viscosity stokes St 104 m2 s1
(dynamic) viscosity poise P 101 N s m2
magnetic flux maxwell Mx 108 Wb
magnetic flux density gauss G 104 T
concentration M 103 mol m3 = mol dm3
6

Units Defined Exactly in Terms of the SI Units

Physical Quantity Name of Unit Symbol Definitiona

length inch in 0.0254 m

mass pound lb 0.453 592 37 kg
time minute min 60 s
time hour h 3600 s
plane angle degree (/180) rad
force kilogram-force kgf 9.806 65 N
pressure standard atmosphere atm 101 325 Pa
pressure conventional millimetre mmHg 13.5951 9.806 65 Pa =
of mercuryb 133.322 Pa

pressure torr Torr (101 523/760) Pa = 133.322 Pa

pressure bar bar 105 Pa
pressure pounds per square inch psi 6894.757 Pa
energy kilowatt hour kW h 3.6 106 J
energy thermochemical calorie calth 4.184 J
electric dipole moment debye D 3.335 64 1030 C m
a
These definitions are exact.
The difference between 1 mmHg and 1 Torr is less than 2 107 Torr.
b
 7

Recommended Values of Fundamental Constants

Fundamental Constant Symbol Value

Avogadro constant L, NA 6.022 1367 1023 mol1

gas constant R 8.314 510 J K1 mol1
Boltzmann constant k, kB 1.380 658 1023 J K1
Faraday constant at T = 298.15 K F 9.648 5309 104 C mol1
( RT/F ) 0.025 693 V
elementary charge e 1.602 177 33 1019 C
electron volt eV 1.602 18 1019 J
LeV = FV 9.648 547 104 J mol1
Planck constant h 6.626 0755 1034 J s
h = h/2 1.054 5726 1034 J s
speed of light in vacuuma c 2.997 924 58 108 m s1
permeability of a vacuuma o 4 107 A2
permittivity of a vacuuma o 8.854 187 816 1012 F m1
rest mass of electron me 9.109 3897 1031 kg
rest mass of proton mp 1.672 6231 1027 kg
Hartree energy Eh 4.359 7482 1018 J
Bohr radius a0 5.291 772 49 1011 m
Bohr magneton B = eh/4 me 9.274 0154 1024 J T1
nuclear magneton = eh/4 mp 5.050 7866 1027 J T1
Rydberg constant R 109 737.315 34 cm1
unified atom mass unit u 1.660 54 1027 kg
gravitational constant G 6.67259 1011 m3 kg1
standard acceleration due to gravitya g 9.806 55 m s2
a
These values are exact.
 SPECTROSCOPIC DATA
INFRARED
Characteristic Wavenumbers, ~ , of Fundamental Absorptions of Organic Functional Groups

~ /cm1
1. OH stretching
free sharp 36503590
intramolecular hydrogen-bonded single bridges sharp 36003450
(excluding chelates)
intermolecular hydrogen bonded polymeric associations broad 34003200
intermolecular chelates and carboxylic acids broad 32002500

2. NH stretching (hydrogen bonding lowers as in OH stretching)

primary amides two bands ~3500 and 3400
primary amines two bands 35003300
secondary amides 34603400
secondary amines 34503300

3. CH stretching
alkynes 3300
alkenes and aryls 30403010
methyls and methylenes two or three bands 29602850
aldehydes 29002700

4. CX stretching
nitriles 22602220
alkynes 22602100

5. X=Y=Z stretching
allenes C=C=C ~1950
azides RN=N+=N 21602120
carbon dioxide O=C=O antisymmetric 2349

6. C=O stretching
(a) Aldehydes
saturated 17401720
aryl 17001650
,-unsaturated 17051680

table continued on next page

 9

Characteristic wavenumbers, ~ , of fundamental absorptions of organic functional groups (continued)

C=O stretching continued ~ /cm1

(b) Ketones
four ring ~1780
five ring 17501740
saturated acyclic, alicyclic six-ring and larger, and ,-unsaturated five ring 17251705
aryl 17001680
,-unsaturated 16851660
(c) Carboxylic acids
saturated 17251700
,-unsaturated 17151690
aryl 17001680
most carboxylate anions 16101550
(d) Esters and lactones
esters of phenols or enols 18001750
five-ring lactones 17801760
,-unsaturated five-ring lactones 17701740
saturated esters and six-ring and larger lactones 17501735
esters of aromatic or ,-unsaturated acids 17301715
(e) Amides and lactams
primary amides two bands ~1690 and 1600
primary amides (solid phase) two bands 1650 and 1640
secondary amides two bands 17001670 and 15501510
secondary amides (solid phase) two bands 16801630 and 15701515
tertiary amides 16701630
four-ring lactams ~1745
five-ring lactams ~1700
six ring and large lactams ~1670
(f) Anhydrides
saturated two bands 18501800 and 17901740
aryl and ,-unsaturated two bands 18301780 and 17701710
(g) Acid chlorides
saturated 18151790
aryl and ,-unsaturated 17901750

7. C=N stretching
imines and oximes variable and of little diagnostic value ~16901640

table continued on next page

10

Characteristic wavenumbers, ~ , of fundamental absorptions of organic functional groups (continued)

~ /cm1
8. C=C stretching
isolated variable 16801620
conjugated one or two bands 16501590
aromatic two bands ~1600 and 1500
aromatic weak or absent when ring is not further conjugated 1580

9. N=O stretching
Nitro compounds asymmetric 15551540
symmetric 13851350

10. Carbonhalogen stretching

CF 14001000
CCl 800 600
CBr 600500
CI 500

11. CH deformations
i-propyl 13851380 13701365
11751165 11701140
t-butyl 13951385 1365
12551245 12501200
RCH=CH2 995985 915905
RCH=CHR (trans) 970960
R2C=CH 895885
R2C=CHR 840790
RCH=CHR (cis) ~690
RCCH ~630

12. NH bend
primary amines and amides 16501560

13. PX stretching
PH 24402350
PPh 1440
POR 12401030
P=O 13001250

14. BH stretching
terminal BH 26502450
bridging BH 20901600
 11

Characteristic Wavenumbers, ~ , of Fundamental Absorptions of Anions and Cations

~ /cm1
ammonium [NH4] + 33003030 14301390

cyanide [CN] 22002000
thiocyanate [SCN] CN stretch 21502050
acetate [CH3CO2] COO antisymmetric stretch 15801550

acetate [CH3CO2] COO symmetric stretch 14301410
2
carbonate [CO3] 14901410
nitrate [NO3] 13801350

perchlorate [ClO4] 11701050
2
sulfate [SO4] 11301080
phosphate [PO4] 3 11001000
2
chromate [CrO4] 885
N-bonded thiocyanate CS stretch 860780
S-bonded thiocyanate CS stretch 720690

Characteristic Wavenumbers, ~ , of Fundamental Absorptions in Coordination Compounds

~ /cm1
Transition metal carbonyls: Wavenumber ranges of these CO stretching
vibrations apply only to unsubstituted, neutral species. Actual values depend
also on the compound and the nature of other ligands attached to the metal.
terminal CO 21501900
bridging CO 19001750
triply bridging or capping CO 18001600

MetalX stretching modes

MH 22501700
M=O 1050950
MF 750500
MCl 400200
MBr 300200
MI 200100
12

NUCLEAR MAGNETIC RESONANCE

Properties of Selected NMR-Active Nuclides

Nuclide Natural Abundance I / 107 rad T1 s1 Relative Receptivity

C values for I= nuclei
are 3C
1
H 99.985% 1/2 26.75 1.00
2
H, D 0.015% 1 4.11 1.45 106
10
B 19.58% 3 2.87 3.93 103
11
B 80.42% 3/2 8.58 0.133
13
C 1.108% 1 6.73 1.76 104
14
N 99.63% 1 1.93 1.00 103
15
N 0.37% 1/2 2.71 3.85 106
17
O 0.037% 5/2 3.63 1.08 105
19
F 100% 1/2 25.18 0.834
23
Na 100% 3/2 7.08 9.27 102
27
Al 100% 5/2 6.98 0.207
29
Si 4.70% 1/2 5.32 3.69 104
31
P 100% 1/2 10.84 0.067
77
Se 7.58% 1/2 5.12 5.30 104
103
Rh 100% 1/2 0.85 3.16 105
107
Ag 51.82% 1/2 1.09 3.48 105
109
Ag 48.18% 1/2 1.25 4.92 105
117
Sn 7.61% 1/2 9.58 3.49 103
119
Sn 8.58% 1/2 10.02 4.51 103
129
Xe 26.44% 1/2 7.44 5.69 103
183
W 14.40% 1/2 1.12 1.06 105
195
Pt 33.8% 1/2 5.77 3.39 103
199
Hg 16.84% 1/2 4.82 9.82 104
 13

Chemical Shifts of Common Functional Groups

Positions of 1H- and 13C-NMR signals in the following tables are given as chemical shifts, ,
expressed as parts per million, ppm, relative to tetramethylsilane, TMS. Usual ranges of values
for 1H-NMR are 015, except that most MH shifts are < 0. For 1H-NMR, values are usually
within 0.2 of those quoted unless inductive, anisotropic or steric effects associated with functional
groups operate. Chemical shifts for 13C-NMR are usually 0250.

Chemical Shifts of 13C Nuclei in Common Functional Groups

Alkanes Ethers
Cyclopropanes 08 CH3O 4560
Cycloalkanes 525 RCH2O 4270
RCH3 525 R2CHO 6577
RCH2R 2245 R3CO 7083
R2CHR 3058
R3CR 2850 Amines
CH3N 1045
Carbonyls RCH2N 4555
RCOOR 160177 R2CH2N 5070
RCOOH 162183 R3CN 6075
RCHO 185205
RCOR 190220 Other Heteroatoms
RCH2S 2242
Halogens RCH2P 1025
CH3X 525 ArP 120130
RCH2X 538 ArN 130138
R2CHX 3962 ArO 130150
R3CX 3575 RCN 118123

Unsaturated Compounds
Aromatics 110133
Alkenes 100143
Alkynes 7595
14

Chemical Shifts of Methyl, Methylene and Methine Protons Attached to Saturated Linkages

Methyl Methylene Methine

CH3C 0.9
CH3CC=C 1.1
CH3CO 1.4 CH2C 1.4 >CHC 1.5
CH3C=C 1.6 CH2CC=C 1.7
CH3CONR 2.0 CH2CO 1.9 >CHCO
CH3C=CCO 2.0
CH3COOR 2.0
CH3S 2.1
CH3COR 2.2 CH2COOR 2.2
CH3I 2.2 CH2CONR 2.2
CH3CHO 2.2 CH2CHO 2.2
CH3Ar 2.3 CH2C=C 2.2
CH3N 2.3 CH2CN 2.3
CH3COOAr 2.4 CH2COR 2.4
CH2S 2.4 >CHCHO 2.4
CH2C=CCO 2.4
CH2N 2.5
CH3COAr 2.6 CH2Ar 2.6
CH3Br 2.6
>CHCOR 2.7
>CHCN 2.7
>CHN 2.8
CH3NCOR 2.9
CH3NAr 3.0
CH3Cl 3.0 >CHAr 3.0
CH2I 3.2 >CHS 3.2
CH3OR 3.3 >CHCOAr 3.3
+
CH3N 3.3
CH3OH 3.4 CH2OR 3.4
CH2Br 3.5
CH2Cl 3.6
CH2OH 3.6
CH3OCOR 3.7 >CHOR 3.7
CH3OAr 3.8 >CHOH 3.9
CH3OC=C 3.8 >CHCl 4.0
CH2OCOR 4.1 >CHBr 4.1
>CHI 4.2
CH2OAr 4.3
>CHOCOR 4.8
 Chemical Shift Ranges of Protons Attached to Unsaturated Linkages

Proton Proton
CCH 1.83.1 C=CHO 6.08.1
CH=CN 3.75.0 Aromatic protons 6.09.0
CH=C=O 4.05.0 CH=CCO 6.57.8
C=CH 4.56.0 HCOO, HCON 8.08.2
C=CHN 5.78.0 RCHO, ArCHO 9.410.5
C=CHCO 5.86.7

Chemical Shift Ranges of MH, OH and NH Protons

Group Range

MH (M = Transition metal) 300 Diagnostic of metal hydride

ROH 210 H-bonded enols usually in range 1116
RNH2 RNHR' 25 Position depends strongly on solvent
ArNH2, ArNHR' 3.56 or larger
RCONH2 58.5 Often very broad (sometimes unobservable)
RCONHCOR' 9ca. 12 Often very broad
RCO2H 10ca. 13

Additivity Table for Estimation of the 1H Chemical Shifts of Methylene Groups

(CH2X1X2) = 1.25 + X1 + X2

substituent Xn substituent Xn sustituent Xn

alkyl 0.0 OCOR 2.7 SH, SR 1.0
vinyl 0.8 NH2, NR2 1.0 SO2R 1.7
alkynyl 0.9 NO2 3.0 -CHO 1.2
phenyl 1.3 F 2.1 -COR 1.2
OH 1.7 Cl 2.0 -CO2H 0.8
OR 1.5 Br 1.9 -CO2R 0.7
OPh 2.3 I 1.4 -CN 1.2
16

1
H1H SpinSpin Coupling Constants

J / Hz J / Hz

C 8 to 18a CH CH O 03
H

CH CH 68b CH C CH 13

H 3C CH2 68b CH C CH 46

H3C

CH 68b CH C C CH 02
H3C

Ha H
aa 813 ortho 69

Heq
ae 26 meta 13
Heq
H
ee 26 para 01
Ha

H H
C CH CH 411 cis 512

C CH CH C 613 trans 1218

H

H
C CH CH O 3 to
58 gem
+3a
H

a
The sign of J is unimportant for first-order spectra.
b
Assumes free rotation.
 17

ULTRAVIOLET and VISIBLE

Absorption band intensities are expressed in terms of the molar absorption coefficient
A
=
cl
where A = dimensionless absorbance, c = molar concentration, and l = path length of the
absorbing species. Units of may therefore be mol1 dm3 cm1 or 103 cm2 mol1.
Absorption bands with maxima, max, below 215 nm are observable only as end absorption.
Compounds containing unconjugated -bands show only end absorption. Saturated aldehydes
and ketones do, however, show a low-intensity band with max = 1030 mol1 dm3 cm1 in the
range 275295 nm.

Absorption Maxima of Substituted Benzenes PhR

solvent: H2O or MeOH

R max max max max max max

/ nm / mol1 / nm / mol1 / nm / mol1
dm3 cm1 dm3 cm1 dm3 cm1

H 203 7400 254 204

+
NH3 203 7500 254 160
Me 206 7000 261 225
Cl, Br 210 7700 262 190
OH 210 6200 270 1450
OMe 217 6400 269 1480
SO2NH2 217 9700 264 740
CN 224 13000 271 1000

CO2 224 8700 268 560
CO2H 230 11600 273 970
NH2 230 8600 280 1430

O 235 9400 287 2600
NHAc 238 10500
CH=CH2 248 1400 282 750 291 500
NO2 268 7800
(E)-CH=CHCO2H 273 21000
18

WoodwardFieser Rules for the Prediction of max Values for * Transitions

of Dienes, Polyenes and ,-Unsaturated Aldehydes, Ketones and Acids
Basic Chromophore: Diene max (EtOH) / nm
Diene 214
Increment / nm
Each additional double bond extending the conjugation 30
a
Each homoannular diene 39
b
The exocyclic nature of any double bond 5
Each alkyl group or ring residue 5
Each auxochrome: OAcyl 0
OAlkyl 6
SAlkyl 30
Cl, Br 5
NAlkyl2 60

Basic Chromophore: , -unsaturated Aldehydes, Ketones and Acids max (EtOH) / nm

Six-ring or acyclic ,-unsaturated ketone 215
Five-ring ,-unsaturated ketone 202
,-unsaturated aldehyde 209
,-unsaturated acid 197

Increment / nm
Each additional double bond extending the conjugation 30
a
Each homoannular diene 39
b
The exocyclic nature of any double bond 5
Each alkyl group or ring residue 10
12
for aldehydes and ketones only 18
Each auxochrome: OH 35
30
50
OAcyl , , 6
OAlkyl 35
30
17
31
SAlkyl 85
Cl 15
12
Br 25
30
NAlkyl2 95

a b
Homoannular diene: Exocyclic double bond:
 19

Typical Electronic Absorption Intensities of Transition Metal Complexes

Type of Transition max / mol1 dm3 cm1

Spin-forbidden, Laporte forbidden 0.011.0

Spin-allowed, Laporte forbidden 1.0100
Spin-allowed, Laporte forbidden, but with dp mixing (Td symmetry)
1001000
and/or intensity stealing
Spin-allowed, Laporte allowed; charge transfer > 1000

Spectrochemical Series
Common Ligands
I < Br <Cl < S2~ SCN <F < OH < O2 ~ H2O < NCS < py < NH3
< ethylenediamine (en) < bipyridine (bipy), PR3 < CH3 < CN CO
Metal Ions
Mn2+ < Ni2+ < Co2+ < Fe2+ < V2+ < Fe3+ < Cr3+ < V3+ < Co3+
< Mn4+ < Mo3+ < Rh3+ < Ru3+ < Pd4+ < Ir3+ < Re4+ < Pt4+

o values for metals of the first transition series are typically in the ranges M2+: 700016000 cm1
and M3+: 1300026000 cm1 for all but the strongest ligands.
In any group o increases with atomic mass of the metal, i.e. 3d < 4d < 5d.
For tetrahedral complexes, t 4
9
o .

(3+ ion) 23 (2+ ion) for isoelectronic ions.

The Trans-Effect Series

CN , CO > PR3, H > CH3 > C6H5 > NO2 , I > Br > Cl > py, NH3 > OH > H2O
20

MASS SPECTROMETRY
Common Fragmentations and Fragment Ions in Mass Spectrometry

Common Fragmentations

m/z Fragment Lost Inference

M 3 to M 14 highest mass peak observed is itself a fragment and not a molecular ion
M 15 CH3
M 17 OH alcohol or carboxylic acid
NH3 primary amine, odd molecular weight
M 18 H2O alcohol, aldehyde, ketone
M 26 C2H2
CN nitrile, odd molecular weight
M 31 CH3O methyl ester or ether
M 35 or M 37 Cl a molecular ion consisting of two peaks of intensity 3:1, two mass
units apart, indicates a monochloro compound
M 43 CH3CO methyl ketone
M 58 CH2=C(OH)CH3 McLafferty rearrangement, methyl ketone with -hydrogen
M 77 C6H5 monosubstituted
M 79 or M 81 Br a molecular ion consisting of two peaks of equal intensity, two mass
units apart, indicates a monobromo compound
M 91 C7H7 benzylic
M 105 C6H5CO aromatic ketone or ester
M 127 I

Fragment Ions

m/z Fragment Inference

18 H2O+
28 CO+, C2H4+, N2+
30 CH2NH2+ primary amine, odd molecular weight
31 CH2OH+ primary alcohol
+
57 C4H9 tert-butyl group
58 CH2=C(OH)CH3 methyl ketone
65 C5H5+ secondary fragment from tropylium ion
+
77 C6H5 monsubstituted aromatic
+
91 C7H7 tropylium ion, usually the base peak
SYMBOLS AND ABBREVIATIONS COMMONLY ENCOUNTERED IN ORGANIC CHEMISTRY

Groups
R alkyl generalised alkyl group
Me methyl CH3
Et ethyl CH2CH3
Pr propyl CH2CH2CH3
i-Pr isopropyl CH(CH3) 2
Bu, n-Bu butyl CH2CH2CH2CH3
i-Bu isobutyl CH2CH(CH3) 2
s-Bu, sec-Bu sec-butyl CH(CH3)CH2CH3
t-Bu, tert-Bu tert-butyl C(CH3)3
Ar aryl generalised aromatic ring
Ph () phenyl C6H5
Ac acetyl (ethanoyl) COCH3
Bn benzyl CH2C6H5
Boc, BOC or t-Boc t-butoxycarbonyl COOC(CH3)3
Bz benzoyl COC6H5
Ms mesyl (methanesulfonyl) SO2CH3
Tf triflyl (trifluoromethanesulfonyl) SO2CF3
Ts tosyl (toluenesulfonyl) SO2C6H4CH3 (para)
TMS trimethylsilyl (or tetramethylsilane in NMR) Si(CH3)3
TBDPS tert-butyldiphenylsilyl SiPh2C(CH3)3
TBS tert-butyldimethylsilyl (also seen as TBDMS) Si(CH3)2C(CH3)3
THP tetrahydropyranyl
Z benzyloxycarbonyl or Cbz C6H5CH2OCO

Reagents, Solvents and Others

aq. aqueous HMPA hexamethylphosphoramide
n-BuLi or nBuLi n-butyllithium h light
cat. catalyst or catalytic IR infrared
D deuterium LDA lithium diisopropylamide
DIBAL diisobutylaluminium hydride mCPBA meta-chloroperoxybenzoic acid
DMAP 4-dimethylaminopyridine NMR nuclear magnetic resonance
DMF N,N-dimethylformamide PCC pyridinium chlorochromate
DMSO dimethyl sulfoxide PDC pyridinium dichromate
DCM dichloromethane TBAF tetra-n-butylammonium fluoride
Et2O diethyl ether TFA trifluoroacetic acid
EI electron impact (ionisation) THF tetrahydrofuran
FAB fast-atom bombardment heat
 THE PROTEINOGENIC AMINO ACIDS
R H R H
For the generalised L-amino acid structure: or in zwitterionic form
H2N CO2H H3N CO2
All have S absolute configuration except cysteine which is R

Amino Acid R Amino Acid R

HS
Glycine (Gly or G) H- Cysteine (Cys or C)

Alanine (Ala or A) CH3- Methionine (Met or M) H3CS

HN
H3C CH3
Valine (Val or V) Histidine (His or H) N

CH3
Leucine (Leu or L) Lysine (Lys or K) H2N
H3C

CH3 H
H3C H2N N
Isoleucine (Ile or I) H Arginine (Arg or R)
NH

HO2C
Phenylalanine (Phe or F) Aspartic acid (Asp or D)

HN
Tryptophan (Trp or W) Glutamic acid (Glu or E) HO2C

O
HO
Serine (Ser or S) Asparagine (Asn or N) H2N

CH3 H2N
H OH
Threonine (Thr or T) Glutamine (Gln or Q)
O
HO

Tyrosine (Tyr or Y)

L-Proline:

H H
Proline (Pro or P): or
N CO2 H N CO2
H H2
23
24

GROUP THEORY
Character Tables

CS = Ch E h
A' 1 1 x, y, Rz x2, y2, z2, xy
A" 1 1 z, Rx, Ry yz, xz

C2v E C2 v(xz) 'v(yz)

A1 1 1 1 1 z x2 , y2 , z2
A2 1 1 1 1 Rz xy
B1 1 1 1 1 x, Ry xz
B2 1 1 1 1 y, Rx yz

C3v E 2C3 3v
A1 1 1 1 z x2 + y 2 , z2
A2 1 1 1 Rz
E 2 1 0 (x, y), (Rx, Ry) (x2 y2, xy) (xz, yz)

C4v E 2C4 C2 2v 2d
A1 1 1 1 1 1 z x2 + y 2 , z2
A2 1 1 1 1 1 Rz
B1 1 1 1 1 1 x2 y2
B2 1 1 1 1 1 xy
E 2 0 2 0 0 (x, y), (Rx, Ry) (xz, yz)

C5v E 2C5 2C52 5v

A1 1 1 1 1 z x2 + y 2 , z2
A2 1 1 1 1 Rz
E1 2 2 cos 72 2 cos 144 0 (x, y), (Rx, Ry) (xz, yz)
E2 2 2 cos 144 2 cos 72 0 (x2 y2, 2xy)
 25

D2h E C2(z) C2(y) C2(x) i v(xy) v(xz) v(yz)

Ag 1 1 1 1 1 1 1 1 x2 , y2 , z2
B1g 1 1 1 1 1 1 1 1 Rz xy
B2g 1 1 1 1 1 1 1 1 Ry xz
B3g 1 1 1 1 1 1 1 1 Rx yz
Au 1 1 1 1 1 1 1 1
B1u 1 1 1 1 1 1 1 1 z
B2u 1 1 1 1 1 1 1 1 y
B3u 1 1 1 1 1 1 1 1 x

D3h E 2C3 3C2 h 2S3 3v

A'1 1 1 1 1 1 1 x2 + y2 , z2
A'2 1 1 1 1 1 1 Rz
E' 2 1 0 2 1 0 (x, y) (x2 y2 , 2xy)
A"1 1 1 1 1 1 1
A"2 1 1 1 1 1 1 z
E" 2 1 0 2 1 0 (Rx, Ry) (xz, yz)

D4h E 2C4 C 2 2C'2 2C"2 i 2S4 h 2v 2d

A1g 1 1 1 1 1 1 1 1 1 1 x2 + y 2 , z2
A2g 1 1 1 1 1 1 1 1 1 1 Rz
B1g 1 1 1 1 1 1 1 1 1 1 x2 y2
B2g 1 1 1 1 1 1 1 1 1 1 xy
Eg 2 0 2 0 0 2 0 2 0 0 (Rx, Ry) (xz, yz)
A1u 1 1 1 1 1 1 1 1 1 1
A2u 1 1 1 1 1 1 1 1 1 1 z
B1u 1 1 1 1 1 1 1 1 1 1
B2u 1 1 1 1 1 1 1 1 1 1
Eu 2 0 2 0 0 2 0 2 0 0 (x, y)
26

D2d = Vd E 2S4 C2 2C'2 2d

A1 1 1 1 1 1 x2 + y 2 , z2
A2 1 1 1 1 1 Rz
B1 1 1 1 1 1 x2 y2
B2 1 1 1 1 1 z xy
E 2 0 2 0 0 (x, y), (Rx, Ry) (xz, yz)

Cv E C2 2C v
A1 + 1 1 1 1 z x2 + y2 , z2
A2 1 1 1 1 Rz
E1 2 2 2 cos 0 (x, y), (Rx, Ry) (xz, yz)
E2 2 2 2 cos 2 0 (x2 y2, xy)
E3 2 2 2 cos 3 0

Dh E 2C v i 2S C2
g +
1 1 1 1 1 1 x2 + y 2 , z2
g 1 1 1 1 1 1 Rz
g 2 2 cos 0 2 2 cos 0 (Rx, Ry) (xz, yz)
g 2 2 cos 2 0 2 2 cos 2 0 (x2 y2, 2xy)

u +
1 1 1 1 1 1 z
u
1 1 1 1 1 1
u 2 2 cos 0 2 2 cos 0 (x, y)
u 2 2 cos 2 0 2 2 cos 2 0

 27

PHYSICAL DEFINITIONS AND FORMULAE

Classical Mechanics

F =m a Newtons Second Law F = force, m = mass, a = acceleration

W =F x W = work done, F = force, x = distance moved
p=m v p = momentum, m = mass, v = velocity
p2 T = kinetic energy, m = mass, v = velocity,
T = 12 m v 2 =
2m p = momentum
F
P= P = pressure, F = force, A = area
A
mg P = pressure, m = mass,
P=
A g = acceleration due to gravity, A = area
m
= = density, m = mass, V = volume
V

mg V g P = pressure exerted by a column of density and

P= = =gh height h where g = acceleration due to gravity,
A A
A = area, V = volume

Electrical Energy

V =I R Ohms Law V = electrical potential I = current, R = resistance

V2t 2 E = energy, V = electrical potential I = current,
E =V I t = = I Rt
R t = time, R = resistance
E
W= W = power, E = energy, t = time
t

Electrostatics

q1 q2 V = potential energy of two charges q1 and q2

V= Coulombs Law
4 0 r separated by r, for a medium of permittivity, 0
q1 q2 F = force acting between two charges q1 and q2
F=
4 0 r 2 separated by r, for a medium of permittivity, 0






   


 
  
  
   






























 























































 






































               













































































































 
    
         



 
                

 
    
  




































































   

























    





































  

  
 



  













 


  
              
 
   
              
  
  
 

     





  

    
 





 
 

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32

PERIODIC TABLE OF THE ELEMENTS

1 2

H He
3 4 5 6 7 8 9 10

Li Be B C N O F Ne
11 12 13 14 15 16 17 18

Na Mg Al Si P S Cl Ar
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54

Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86

Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
87 88 89 104 105 106 107 108 109

Fr Ra Ac Rf Db Sg Bh Hs Mt
58 59 60 61 62 63 64 65 66 67 68 69 70 71

Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
90 91 92 93 94 95 96 97 98 99 100 101 102 103

Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr