Neopentane


Neopentane
Neopentane
Identifiers
CAS number 463-82-1 YesY
PubChem 10041
ChemSpider 9646 YesY
EC number 207-343-7
MeSH Neopentane
ChEBI CHEBI:30358 YesY
Jmol-3D images Image 1
Properties
Molecular formula C5H12
Molar mass 72.15 g mol−1
Exact mass 72.093900384 g mol−1
Appearance Colorless gas
Density 0.627 g cm-3
Melting point

−17 °C, 256 K, 1 °F

Boiling point

10 °C, 283 K, 50 °F

Thermochemistry
Std enthalpy of
formation
ΔfHo298
−168 kJ mol-1
Std enthalpy of
combustion
ΔcHo298
−3514 kJ mol-1
Standard molar
entropy
So298
217 J K−1 mol−1
Hazards
EU Index 601-005-00-6
EU classification Flammable F+Dangerous for the Environment (Nature) N
R-phrases R12, R51/53
S-phrases (S2), S9, S16, S33, S61
NFPA 704
NFPA 704.svg
4
1
0
Related compounds
Related Tetraalkylcarbons Tetra-tert-butylmethane
Related compounds Tetramethylsilane

Tetramethyltin

 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Neopentane, also called 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 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

Nomenclature

IUPAC nomenclature retains the trivial name neopentane.[1][2] The systematic name is 2,2-dimethylpropane, but the substituent numbers are unnecessary because it is the only possible "dimethylpropane".

A neopentyl group attached to a generic group R.

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

Physical properties

Boiling and melting points

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.

The melting point of neopentane (-16.6°C), on the other hand, is some 140 degrees higher than that of isopentane (-159.9°C) and some 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 n-pentane and isopentane.[3]

NMR spectrum

Neopentane has Td symmetry. As a result, all protons are chemically equivalent leading to a single NMR chemical shift δ = 0.902 when dissolved in carbon tetrachloride.[4] 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.

References

  1. ^ Table 19(a) Acyclic and monocyclic hydrocarbons. Parent hydrocarbons
  2. ^ Panico, R.; & Powell, W. H. (Eds.) (1994). A Guide to IUPAC Nomenclature of Organic Compounds 1993. Oxford: Blackwell Science. ISBN 0-632-03488-2. 
  3. ^ James Wei (1999), Molecular Symmetry, Rotational Entropy, and Elevated Melting Points. Ind. Eng. Chem. Res., volume 38 issue 12, pp. 5019–5027 doi:10.1021/ie990588m
  4. ^ Spectral Database for Organic Compounds, Proton NMR spectrum of neopentane, accessed 19 Nov 2006.

External links


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Look at other dictionaries:

  • néopentane — ● néopentane nom masculin Dénomination courante du tétraméthylméthane (CH3)4C …   Encyclopédie Universelle

  • Néopentane — 2,2 diméthylpropane Néopentane Structure du néopentane …   Wikipédia en Français

  • neopentane — neopentanas statusas T sritis chemija formulė C(CH₃)₄ atitikmenys: angl. neopentane rus. неопентан ryšiai: sinonimas – 2,2 dimetilpropanas …   Chemijos terminų aiškinamasis žodynas

  • neopentane — noun The aliphatic hydrocarbon dimethylpropane; isomeric with pentane and isopentane …   Wiktionary

  • neopentane — neo·pentane …   English syllables

  • neopentane — |nē(ˌ)ō+ noun Etymology: ne + pentane : a gaseous or very volatile liquid hydrocarbon (CH3)4C found in small amounts in petroleum and natural gas; dimethyl propane or tetramethyl methane …   Useful english dictionary

  • 2,2-diméthylpropane — Néopentane Structure du néopentane Général …   Wikipédia en Français

  • Pentane — n Pentane …   Wikipedia

  • 463-82-1 — 2,2 diméthylpropane Néopentane Structure du néopentane …   Wikipédia en Français

  • Diméthylpropane — 2,2 diméthylpropane Néopentane Structure du néopentane …   Wikipédia en Français


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