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 | ||
EC Number |
| ||
1850 | |||
MeSH | neopentane | ||
PubChem CID | |||
UNII | |||
UN number | 2044 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
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 constant (kH) | 4.7 nmol Pa−1 kg−1 | ||
Thermochemistry | |||
Heat capacity (C) | 121.07–120.57 J K−1 mol−1 | ||
Std molar entropy (S⦵298) | 217 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) | −168.5–−167.3 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | −3.51506–−3.51314 MJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H220, H411 | |||
P210, P273, P377, P381, P391, P403, P501 | |||
NFPA 704 (fire diamond) | |||
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). |
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.
It was first synthesized by Russian chemist Mikhail Lvov in 1870. [4]
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 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]
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]
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]
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]
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.
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.
Cis–trans 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. Cis–trans 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.
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.
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.
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.
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.
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.
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.
Isopentane, also called methylbutane or 2-methylbutane, is a branched-chain saturated hydrocarbon with five carbon atoms, with formula C
5H
12 or CH(CH
3)
2(C
2H
5).
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.
Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane.
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.
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.
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.