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Neopentane
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Neopentane
Names
Preferred IUPAC name
2,2-Dimethylpropane[2]
Other names
Neopentane
Tetramethylmethane[1]
Identifiers
CAS Number  463-82-1
3D model (JSmol)  Interactive image
Beilstein Reference 1730722
ChEBI  CHEBI:30358
ChemSpider  9646
ECHA InfoCard 100.006.677
EC Number  207-343-7
Gmelin Reference 1850
MeSH neopentane
PubChem CID  10041
UNII  M863R1J0BP
CompTox Dashboard (EPA)  DTXSID6029179
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InChI
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SMILES
Properties
Chemical formula C5H12
Molar mass 72.151 g·mol−1
Appearance Colorless gas
Odor Odorless
Density 3.255 kg/m3 (gas, 9.5 °C)
601.172 kg/m3 (liquid, 9.5 °C)
Melting point −16.5 °C (2.3 °F; 256.6 K)
Boiling point 9.5 °C (49.1 °F; 282.6 K)
Vapor pressure 146 kPa (at 20 °C)[3]
Henry's law 4.7 nmol Pa−1 kg−1

constant (kH)
Thermochemistry
Heat capacity (C) 121.07–120.57 J K−1 mol−1
Std molar 217 J K−1 mol−1

entropy (So298)
Std enthalpy of −168.5–−167.3 kJ mol−1

formation (ΔfH ⦵
298 )
Std enthalpy of −3.51506–−3.51314 MJ mol−1
combustion (ΔcH⦵298)
Hazards
EU classification (DSD) (outdated)
F+ N
R-phrases (outdated) R12, R51/53
S-phrases (outdated) (S2), S16, S33
NFPA 704 (fire diamond)
1
4
0
Related compounds
Related alkanes  2,2-Dimethylbutane
 2,3-Dimethylbutane
 Triptane
 Tetramethylbutane
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
Neopentane, also called 2,2-dimethylpropane, is a double-branched-

chain alkane with five carbon atoms. Neopentane is a 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, and has
achiral tetrahedral symmetry. It is one of the three structural isomers with
the molecular formula C5H12 (pentanes), the other two being n-
pentane and isopentane. Out of these three, it is the only one to be a gas at standard
conditions; the others are liquids.
Contents
 1Nomenclature
 2Physical properties
o 2.1Boiling and melting points
o 2.21H NMR spectrum
 3References
 4External links
Nomenclature[edit]
The traditional name neopentane was still retained in the
1993 IUPAC recommendations,[4][5] but is no longer recommended according to the
2013 recommendations.[2] The preferred IUPAC name is the systematic name 2,2-
dimethylpropane, but the substituent numbers are superfluous because it is the only
possible “dimethylpropane”.[citation needed]
A neopentyl group attached to a generic group R.
A neopentyl substituent, often symbolized by "Np", has the structure Me 3C–CH2– for

instance neopentyl alcohol (Me3CCH2OH or NpOH). As Np also symbolises the
element neptunium (atomic number 93) one should use this abbreviation with care.
The obsolete name tetramethylmethane is also used, especially in older sources. [6][7]
Physical properties[edit]
Boiling and melting points[edit]
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 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 resulting from higher molecular symmetry. Indeed,
the entropy of fusion of neopentane is about four times lower than that of n-pentane
and isopentane.[8]
H NMR spectrum[edit]
1
Because of neopentane's full tetrahedral symmetry, all protons are chemically

equivalent, leading to a single NMR chemical shift δ = 0.902 when dissolved
in carbon tetrachloride.[9] 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.[10]
References[edit]
1. ^ Aston, J.G.; Messerly, G.H., Heat Capacities and Entropies of Organic Compounds II.
Thermal and Vapor Pressure Data for Tetramethylmethane from 13.22K to the Boiling
Point. The Entropy from its Raman Spectrum, J. Am. Chem. Soc., 1936, 58, 2354.
2. ^ Jump up to:a b "Front Matter". Nomenclature of Organic Chemistry : IUPAC
Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal
Society of Chemistry. 2014. p. 652. doi:10.1039/9781849733069-FP001. ISBN 978-0-
85404-182-4.
3. ^ https://pubchem.ncbi.nlm.nih.gov/compound/neopentane#section=Vapor-Pressure
4. ^ Table 19(a) Acyclic and monocyclic hydrocarbons. Parent hydrocarbons
5. ^ Panico, R. & Powell, W. H., eds. (1994). A Guide to IUPAC Nomenclature of Organic
Compounds 1993. Oxford: Blackwell Science. ISBN 978-0-632-03488-8.
6. ^ Whitmore, Frank C.; Fleming, Geo. H. (1934-09-01). "Preparation of
Tetramethylmethane (Neopentane) and Determination of its Physical
Constants1". Journal of the American Chemical Society. 55 (9): 3803–
3806. doi:10.1021/ja01336a058. ISSN 0002-7863.
7. ^ LaCoste, Lucien J. B. (1934-10-15). "The Rotational Wave Equation of
Tetramethylmethane for Zero Potential and a Generalization". Physical Review. 46 (8):
718–724. doi:10.1103/PhysRev.46.718.
8. ^ Wei, James (1999). "Molecular Symmetry, Rotational Entropy, and Elevated Melting
Points". Ind. Eng. Chem. Res. 38 (12): 5019–5027. doi:10.1021/ie990588m.
9. ^ Spectral Database for Organic Compounds, Proton NMR spectrum of neopentane,
accessed 4 Jun 2018.
10. ^ Haesler, Jacques; Schindelholz, Ivan; Riguet, Emmanuel; Bochet, Christian G.; Hug,
Werner (2007). "Absolute configuration of chirally deuterated
neopentane" (PDF). Nature. 446 (7135): 526–
529. doi:10.1038/nature05653. PMID 17392783. S2CID 4423560.
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Neopentane

From Wikipedia, the free encyclopedia

Preferred IUPAC name

CAS Number  463-82-1

3D model (JSmol)  Interactive image

Beilstein Reference 1730722

ECHA InfoCard 100.006.677

Gmelin Reference 1850

CompTox Dashboard (EPA)  DTXSID6029179

Chemical formula C5H12

Molar mass 72.151 g·mol−1

Appearance Colorless gas

Density 3.255 kg/m3 (gas, 9.5 °C)

601.172 kg/m3 (liquid, 9.5 °C)

Melting point −16.5 °C (2.3 °F; 256.6 K)

Boiling point 9.5 °C (49.1 °F; 282.6 K)

Vapor pressure 146 kPa (at 20 °C)[3]

Henry's law 4.7 nmol Pa−1 kg−1

Heat capacity (C) 121.07–120.57 J K−1 mol−1

Std molar 217 J K−1 mol−1

Std enthalpy of −168.5–−167.3 kJ mol−1

Related alkanes  2,2-Dimethylbutane

Except where otherwise noted, data are given for materials in

verify (what is ?)

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

A neopentyl group attached to a generic group R.

A neopentyl substituent, often symbolized by "Np", has the structure Me 3C–CH2– for

Because of neopentane's full tetrahedral symmetry, all protons are chemically

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