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Neopentane



Neopentane
General
IUPAC preferred name neopentane
Systematic name 2,2-dimethylpropane
Molecular formula C5H12
SMILES CC(C)(C)C
Molar mass 72.15 g mol−1
Appearance colorless gas
CAS number [463-82-1]
Properties
Density and phase  ? g/l, gas
Solubility in water  ? g/100 ml (? °C)
Melting point −18 °C (255 K)
Boiling point 10 °C (283 K)
Thermodynamic data
Std enthalpy change
of formation
, ΔfHogas
−168 kJ/mol
Std enthalpy change
of combustion
, ΔcH°gas
−3514 kJ/mol
Standard molar
entropy
, S°liquid
217 J·K−1·mol−1
Hazards
MSDS External MSDS
EU classification Highly flammable (F+)
Dangerous for
the environment (N)
NFPA 704
4
1
0
 
R-phrases R12, R51/53
S-phrases (S2), S9, S16, S33, S61
Flash point flammable gas
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related alkanes Pentane
Isopentane
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Neopentane, also called dimethylpropane or 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.

Additional recommended knowledge

Contents

Nomenclature

IUPAC nomenclature retains the trivial name neopentane.[1] Dimethylpropane is the systematic name. The respective substituent numbers (the 2,2-) are unnecessary because there can be no isomers of this molecule with dimethylpropane as part of their names.

A neopentyl substituent or a neopentyl compound has the structure Me3C-CH2- for instance neopentyl alcohol.

Isomers

Neopentane is one of three structural isomers with the molecular formula C5H12, the others being pentane and isopentane.

Proton NMR spectrum

Neopentane has Td symmetry. As a result, all protons are chemically equivalent leading to a single chemical shift at δ 0.902 in carbon tetrachloride.[2] This is similar to the silane analog, tetramethylsilane which has a single chemical shift, defined as δ 0 by convention.

Related

Chirally deuterated neopentane ([2H1,2H2,2H3]-neopentane) is an interesting molecule. The neopentane is rendered chiral by the isotopic substitution of hydrogen . Its chirality arises solely by the mass distribution of its nuclei, while its electron distribution is completely achiral.

References

  1. ^ http://www.acdlabs.com/iupac/nomenclature/93/r93_679.htm
  2. ^ Spectral Database for Organic Compounds, Proton NMR spectrum of neopentane, accessed 19 Nov 2006.
  • Panico, R.; & Powell, W. H. (Eds.) (1994). A Guide to IUPAC Nomenclature of Organic Compounds 1993. Oxford: Blackwell Science. ISBN 0-632-03488-2. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Neopentane". A list of authors is available in Wikipedia.
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