Neopentane

Last updated
Neopentane
2,2-dimethylpropane.png
Neopentane.PNG
Ball and stick model of neopentane Neopentane-3D-balls.png
Ball and stick model of neopentane
Spacefill model of neopentane Neopentane-3D-vdW.png
Spacefill model of neopentane
Names
Preferred IUPAC name
2,2-Dimethylpropane [1]
Other names
Neopentane
Tetramethylmethane [2]
Identifiers
3D model (JSmol)
1730722
ChEBI
ChemSpider
ECHA InfoCard 100.006.677 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-343-7
1850
MeSH neopentane
PubChem CID
UNII
UN number 2044
  • InChI=1S/C5H12/c1-5(2,3)4/h1-4H3 Yes check.svgY
    Key: CRSOQBOWXPBRES-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C)C
Properties
C5H12
Molar mass 72.151 g·mol−1
AppearanceColorless 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]
4.7 nmol Pa−1 kg−1
Thermochemistry
121.07–120.57 J K−1 mol−1
Std molar
entropy
(S298)
217 J K−1 mol−1
−168.5–−167.3 kJ mol−1
−3.51506–−3.51314 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-pollu.svg
Danger
H220, H411
P210, P273, P377, P381, P391, P403, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
4
0
Related compounds
Related alkanes
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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.

It was first synthesized by Russian chemist Mikhail Lvov  [ ru ] in 1870. [4]

Nomenclature

The traditional name neopentane, coined by William Odling in 1876, [5] was still retained in the 1993 IUPAC recommendations, [6] [7] but is no longer recommended according to the 2013 recommendations. [1] The preferred IUPAC name is the systematic name 2,2-dimethylpropane, but the substituent numbers are superfluous because it is the only possible “dimethylpropane”.

A neopentyl group attached to a generic group R. Neopentyl-group-2D-skeletal.png
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). 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. [8] [9]

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 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. [10]

1H NMR spectrum

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. [11] 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. [12]

Derivatives

The alcohol pentaerythritol can be described as the result of replacing one hydrogen in each of the four methyl groups by a hydroxyl (–OH) group.

A linear polymer with alternating neopentane and orthocarbonate groups, which can be described as an ester (pentaerythritol orthocarbonate) with formula [(−CH2)2C(CH2−)2 (−O)2C(O−)2]n, was synthesized in 2002. [13]

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Alkene</span> Hydrocarbon compound containing one or more C=C bonds

In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.

<i>Cis</i>–<i>trans</i> isomerism Pairs of molecules with same chemical formula showing different spatial orientations

Cistrans isomerism, also known as geometric isomerism, describes certain arrangements of atoms within molecules. The prefixes "cis" and "trans" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, cis indicates that the functional groups (substituents) are on the same side of some plane, while trans conveys that they are on opposing (transverse) sides. Cistrans isomers are stereoisomers, that is, pairs of molecules which have the same formula but whose functional groups are in different orientations in three-dimensional space. Cis and trans isomers occur both in organic molecules and in inorganic coordination complexes. Cis and trans descriptors are not used for cases of conformational isomerism where the two geometric forms easily interconvert, such as most open-chain single-bonded structures; instead, the terms "syn" and "anti" are used.

In chemistry, a structural isomer of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metamer was formerly used for the same concept.

<span class="mw-page-title-main">Pentaerythritol</span> Chemical compound

Pentaerythritol is an organic compound with the formula C(CH2OH)4. The molecular structure can be described as a neopentane with one hydrogen atom in each methyl group replaced by a hydroxyl (–OH) group. It is therefore a polyol, specifically a tetrol.

<span class="mw-page-title-main">Enantiomer</span> Stereoisomers that are nonsuperposable mirror images of each other

In chemistry, an enantiomer – also called optical isomer, antipode, or optical antipode – is one of two stereoisomers that are nonsuperposable onto their own mirror image. Enantiomers of each other are much like one's right and left hands; without mirroring one of them, hands cannot be superposed onto each other. It is solely a relationship of chirality and the permanent three-dimensional relationships among molecules or other chemical structures: no amount of re-orientiation of a molecule as a whole or conformational change converts one chemical into its enantiomer. Chemical structures with chirality rotate plane-polarized light. A mixture of equal amounts of each enantiomer, a racemic mixture or a racemate, does not rotate light.

<span class="mw-page-title-main">Stereocenter</span> Atom which is the focus of stereoisomerism in a molecule

In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups creates a new stereoisomer. Stereocenters are also referred to as stereogenic centers.

<span class="mw-page-title-main">Pentane</span> Alkane with 5 carbon atoms

Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer, in which case pentanes refers to a mixture of them; the other two are called isopentane (methylbutane) and neopentane (dimethylpropane). Cyclopentane is not an isomer of pentane because it has only 10 hydrogen atoms where pentane has 12.

In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula −C4H9, derived from either of the two isomers (n-butane and isobutane) of butane.

<span class="mw-page-title-main">Chirality (chemistry)</span> Geometric property of some molecules and ions

In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality. The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.

<span class="mw-page-title-main">Axial chirality</span> Type of symmetry in molecules

In chemistry, axial chirality is a special case of chirality in which a molecule contains two pairs of chemical groups in a non-planar arrangement about an axis of chirality so that the molecule is not superposable on its mirror image. The axis of chirality is usually determined by a chemical bond that is constrained against free rotation either by steric hindrance of the groups, as in substituted biaryl compounds such as BINAP, or by torsional stiffness of the bonds, as in the C=C double bonds in allenes such as glutinic acid. Axial chirality is most commonly observed in substituted biaryl compounds wherein the rotation about the aryl–aryl bond is restricted so it results in chiral atropisomers, as in various ortho-substituted biphenyls, and in binaphthyls such as BINAP.

<span class="mw-page-title-main">Isopentane</span> Chemical compound

Isopentane, also called methylbutane or 2-methylbutane, is a branched-chain saturated hydrocarbon with five carbon atoms, with formula C
5
H
12
or CH(CH
3
)
2
(C
2
H
5
)
.

<span class="mw-page-title-main">Orthocarbonic acid</span> Hypothetical compound with formula C(OH)4

Orthocarbonic acid, carbon hydroxide, methanetetrol is the name given to a hypothetical compound with the chemical formula H4CO4 or C(OH)4. Its molecular structure consists of a single carbon atom bonded to four hydroxyl groups. It would be therefore a fourfold alcohol. In theory it could lose four protons to give the hypothetical oxocarbon anion orthocarbonateCO4−4, and is therefore considered an oxoacid of carbon.

<span class="mw-page-title-main">Pentyl group</span> Chemical compound

Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane.

<span class="mw-page-title-main">2,2-Dimethylbutane</span> Chemical compound

2,2-Dimethylbutane, trivially known as neohexane at William Odling's 1876 suggestion, is an organic compound with formula C6H14 or (H3C-)3-C-CH2-CH3. It is therefore an alkane, indeed the most compact and branched of the hexane isomers — the only one with a quaternary carbon and a butane (C4) backbone.

<span class="mw-page-title-main">Binary silicon-hydrogen compounds</span>

Silanes are saturated chemical compounds with the empirical formula SixHy. They are hydrosilanes, a class of compounds that includes compounds with Si−H and other Si−X bonds. All contain tetrahedral silicon and terminal hydrides. They only have Si−H and Si−Si single bonds. The bond lengths are 146.0 pm for a Si−H bond and 233 pm for a Si−Si bond. The structures of the silanes are analogues of the alkanes, starting with silane, SiH4, the analogue of methane, continuing with disilane Si2H6, the analogue of ethane, etc. They are mainly of theoretical or academic interest.

Heat of formation group additivity methods in thermochemistry enable the calculation and prediction of heat of formation of organic compounds based on additivity. This method was pioneered by S. W. Benson.

<span class="mw-page-title-main">Chirality</span> Difference in shape from a mirror image

Chirality is a property of asymmetry important in several branches of science. The word chirality is derived from the Greek χείρ (kheir), "hand", a familiar chiral object.

Bromopentanes are a group of bromoalkanes consisting of pentane isomers with one or more hydrogen atoms replaced by bromine atoms. They have the formula C5H12–nBrn, where n = 1–12 is the number of bromine atoms. They are colorless liquids.

In chemical nomenclature, a descriptor is a notational prefix placed before the systematic substance name, which describes the configuration or the stereochemistry of the molecule. Some of the listed descriptors should not be used in publications, as they no longer accurately correspond with the recommendations of the IUPAC. Stereodescriptors are often used in combination with locants to clearly identify a chemical structure unambiguously.

References

  1. 1 2 "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.
  2. 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.
  3. "Neopentane | C5H12 - PubChem".
  4. Zeitschrift für Chemie (in German). Quandt & Händel. 1870.
  5. Philosophical Magazine. Taylor & Francis. 1876.
  6. Table 19(a) Acyclic and monocyclic hydrocarbons. Parent hydrocarbons
  7. 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.
  8. 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.
  9. 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. Bibcode:1934PhRv...46..718L. doi:10.1103/PhysRev.46.718.
  10. Wei, James (1999). "Molecular Symmetry, Rotational Entropy, and Elevated Melting Points". Ind. Eng. Chem. Res. 38 (12): 5019–5027. doi:10.1021/ie990588m.
  11. Spectral Database for Organic Compounds, Proton NMR spectrum of neopentane, accessed 4 Jun 2018.
  12. Haesler, Jacques; Schindelholz, Ivan; Riguet, Emmanuel; Bochet, Christian G.; Hug, Werner (2007). "Absolute configuration of chirally deuterated neopentane" (PDF). Nature . 446 (7135): 526–529. Bibcode:2007Natur.446..526H. doi:10.1038/nature05653. PMID   17392783. S2CID   4423560.
  13. Vodak, David T.; Braun, Matthew; Iordanidis, Lykourgos; Plévert, Jacques; Stevens, Michael; Beck, Larry; Spence, John C. H.; O'Keeffe, Michael; Yaghi, Omar M. (2002). "One-Step Synthesis and Structure of an Oligo(spiro-orthocarbonate)". Journal of the American Chemical Society. 124 (18): 4942–4943. doi:10.1021/ja017683i. PMID   11982342.