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Introduction to Butane Conformations

The hydrocarbon butane has a more complex and larger set of conformations that are related with its constitution than ethane. Of specific importance and interest are the conformations produced by rotation about the central carbon-carbon bond. Along with these we shall concentrate on two staggered conformers (i.e. A & C) and two eclipsed conformers (i.e. B & D), shown below in the diagram various stereo-representations. Like the staggered conformers are more stable than the eclipsed conformers with 2.8 to 4.5 kcal/mol in case of ethane. Since the staggered conformers represent the major components of a butane sample they have been given the identifying prefix designations anti for A and gauche for C.

Four Conformers of Butane

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The diagram demonstrates the change in potential energy that occurs with rotation about the C2-C3 bond. The model is displayed in conformation D, and via clicking on any of the colored data points on the potential energy curve, it will change to the conformer consequent to that point. The full rotation will be shown by turning the animation on.

It is useful to summarize some significant features of conformational stereoisomerism at this time.

(i)   At room temperature several conformational interconversions in simple molecules occur swiftly.                                                  Subsequently, isolation of pure conformers is usually not possible.
(ii)   Particular conformers need special nomenclature terms like staggered, eclipsed, and gauche and anti when they are selected.
(iii)   Particular conformers may also be designated by dihedral angles. The dihedral angles formed by the two methyl groups about the central double bond are: A 180º, B 120º, C 60º & D0º in the butane conformers that are shown above in the diagram.
(iv)   Than the corresponding eclipsed conformations the staggered conformations about carbon-carbon single bonds are more stable (have a lower potential energy). Eclipsing strain is The higher energy of eclipsed bonds.
(v)   Than the anti-conformer in butane the gauche-conformer is less stable, by about 0.9 kcal/mol. This is because of a crowding of the two methyl groups in the gauche structure, and is called steric hindrance or steric strain.
(vi)   Butane conformers B & C have non-identical mirror image structures in which the clockwise dihedral angles are 300º & 240º correspondingly.

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