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The anti conformer is, therefore, the most stable (≈ 0 kcal/mol). The three eclipsed conformations with dihedral angles of 0°, 120°, and 240° are transition states between conformers. [ 6 ]
In the study of conformational isomerism, the gauche effect is an atypical situation where a gauche conformation (groups separated by a torsion angle of approximately 60°) is more stable than the anti conformation (180°). [2] Relative conformation energy diagram of butane as a function of dihedral angle. [3]
These six conformations can be represented in a relative energy diagram. Butane molecule represented on a staggered and eclipsed Newman projection down a carbon-carbon bond Butane molecule and all of its possible Newman conformations represented on a relative energy diagram. The diagram takes staggered and eclipsed conformations, as well as ...
More complex molecules, such as butane, have more than one possible staggered conformation. The anti conformation of butane is approximately 0.9 kcal mol −1 (3.8 kJ mol −1) more stable than the gauche conformation. [1] Both of these staggered conformations are much more stable than the eclipsed conformations.
Conformations form when butane rotates about one of its single covalent bond. Torsional/dihedral angle is shown on x-axis. Conformations (according to IUPAC): A: antiperiplanar, anti or trans B: synclinal or gauche C: anticlinal or eclipsed D: synperiplanar or cis Valleys of the pink graph are conformations lowest in energy (shown as A & B).
This conformation is more specifically referred to as the gauche conformation of butane. This is due to the fact that the methyl groups are staggered, but only 60° from one another. This conformation is more energetically favored than the eclipsed conformation, but it is not the most energetically favorable conformation.
Butane is the most commonly abused volatile substance in the UK, and was the cause of 52% of solvent related deaths in 2000. [36] By spraying butane directly into the throat, the jet of fluid can cool rapidly to −20 °C (−4 °F) by expansion, causing prolonged laryngospasm . [ 37 ] "
Juxtaposing the designations produces the following terms for the conformers of butane (see Alkane stereochemistry for an explanation of conformation nomenclature): gauche butane is syn-clinal (+sc or −sc, depending on the enantiomer), anti butane is anti-periplanar, and eclipsed butane is syn-periplanar. [2]