Neopentane

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Neopentane, also called 2,2-dimethylpropane, is a

double-branched-chain alkane with five carbon atoms.
Neopentane is an extremely flammable gas at room
temperature and pressure which can condense into a
highly volatile liquid on a cold day, in an ice bath, or
when compressed to a higher pressure.

Neopentane

Neopentane is the simplest alkane with a quaternary

carbon. It is one of the three structural isomers with the
molecular formula C5H12 (pentanes), the other two
being n-pentane and isopentane.

Contents
1 Nomenclature
2 Physical properties
2.1 Boiling and melting points
2.2 NMR spectrum
3 References
4 External links

Names
IUPAC name
2,2-Dimethylpropane[1]

Nomenclature
IUPAC nomenclature retains the trivial name
neopentane.[3][4] The systematic name is 2,2dimethylpropane, but the substituent numbers are
superfluous because it is the only possible
"dimethylpropane."

A neopentyl
group attached
to a generic
group R.

Identifiers
CAS Registry 463-82-1
Number
Beilstein
1730722
Reference
ChEBI

CHEBI:30358

ChemSpider 9646

A neopentyl substituent, often

symbolized by "Np", has the
structure Me3C-CH2- for
instance neopentyl alcohol
(Me3CCH2OH or NpOH). As

EC number

207-343-7

Gmelin
Reference

1850

Jmol-3D

Image

Np also symbolises the element

neptunium (atomic number 93)
one should use this abbreviation
with care.

images

(http://chemapps.stolaf.edu/jmol/jmol.php?
model=CC%28C%29%28C%29C)

MeSH

neopentane

PubChem

10041

InChI

Physical properties

SMILES

Boiling and melting points

Chemical
formula

Properties
C5 H12

The boiling point of neopentane is only 9.5 C,

significantly lower than those of isopentane (27.7 C)
and normal pentane (36.0 C). Therefore, neopentane
is a gas at room temperature and atmospheric
pressure, while the other two isomers are (barely)
liquids.

Molar mass

The melting point of neopentane (-16.6 C), on the

other hand, is 140 degrees higher than that of
isopentane (-159.9 C) and 110 degrees higher than
that of n-pentane (-129.8 C). This anomaly has been
attributed to the better solid-state packing assumed to
be possible with the tetrahedral neopentane molecule;
but this explanation has been challenged on account of
it having a lower density than the other two isomers.
Moreover, its enthalpy of fusion is lower than the
enthalpies of fusion of both n-pentane and isopentane,
thus indicating that its high melting point is due to an
entropy effect. Indeed, the entropy of fusion of
neopentane is about 4 times lower than that of npentane and isopentane.[2]

Boiling point 9.0 to 10.0 C; 48.1 to 49.9 F; 282.1 to

283.1 K

NMR spectrum
Neopentane has Td symmetry. As a result, all protons
are chemically equivalent leading to a single NMR
chemical shift = 0.902 when dissolved in carbon
tetrachloride.[5] In this respect, neopentane is similar to
its silane analog, tetramethylsilane, whose single
chemical shift is zero by convention.
The symmetry of the neopentane molecule can be
broken if some hydrogen atoms are replaced by
deuterium atoms. In particular, if each methyl group has
a different number of substituted atoms (0, 1, 2, and
3), one obtains a chiral molecule. The chirality in this
case arises solely by the mass distribution of its nuclei,
while the electron distribution is still essentially
achiral.[6]

References

72.15 gmol1

Appearance Colorless gas

Odor

Odorless

Density

586 mg mL1[2]

Melting point 21 to 15 C; 6 to 5 F; 252 to 258 K

Henry's law 4.7 nmol Pa1 kg1

constant (k H)
Thermochemistry
Specific
121.07120.57 J K1 mol1
heat capacity
(C)
Std molar
217 J K1 mol1
entropy
(So 298 )
Std enthalpy 168.5167.3 kJ mol1
of
formation
(fHo 298 )
Std enthalpy 3.515063.51314 MJ mol1
of
combustion
(cHo 298 )
Hazards
EU Index

601-005-00-6

EU
classification

F+

R-phrases

R12, R51/53

S-phrases

(S2), S16, S33

NFPA 704

4
1

Related compounds
Related
alkanes

2,2-Dimethylbutane
2,3-Dimethylbutane
Triptane
Tetramethylbutane

1. "neopentane - Compound Summary"

Except where otherwise noted, data are given for

materials in their standard state (at 25 C [77 F],
100 kPa).
verify (what is: / ?)
Infobox references

2.
3.
4.
5.

6.

(http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10041&loc=ec_rcs#x291). PubChem
Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and
Related Records. Retrieved 8 March 2012.
James Wei (1999), Molecular Symmetry, Rotational Entropy, and Elevated Melting Points. Ind. Eng. Chem.
Res., volume 38 issue 12, pp. 50195027 doi:10.1021/ie990588m (https://dx.doi.org/10.1021%2Fie990588m)
Table 19(a) Acyclic and monocyclic hydrocarbons. Parent hydrocarbons
(http://www.acdlabs.com/iupac/nomenclature/93/r93_679.htm)
Panico, R.; & Powell, W. H. (Eds.) (1994). A Guide to IUPAC Nomenclature of Organic Compounds 1993.
Oxford: Blackwell Science. ISBN 0-632-03488-2.
Spectral Database for Organic Compounds, Proton NMR spectrum of neopentane
(http://www.aist.go.jp/RIODB/SDBS/cgi-bin/cre_frame_disp.cgi?spectrum_type=hnmr&sdbsno=5425),
accessed 19 Nov 2006.
Nature. 2007 Mar 29. Absolute configuration of chirally deuterated neopentane. Haesler Jacques, Schindelholz
Ivan, Riguet Emmanuel, Bochet Christian G, Hug Werner.

External links
Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database
Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov
IUPAC Nomenclature of Organic Chemistry (http://www.acdlabs.com/iupac/nomenclature/) (online
version of the "Blue Book")
Retrieved from "https://en.wikipedia.org/w/index.php?title=Neopentane&oldid=668336512"
Categories: Alkanes
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