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The two have equal free energy; neither is more stable, so neither predominates compared to the other. A negative difference in free energy means that a conformer interconverts to a thermodynamically more stable conformation, thus the equilibrium constant will always be greater than 1.
Cyclohexane is the most stable of the cycloalkanes, due to the stability of adapting to its chair conformer. [4] This conformer stability allows cyclohexane to be used as a standard in lab analyses. More specifically, cyclohexane is used as a standard for pharmaceutical reference in solvent analysis of pharmaceutical compounds and raw materials.
The gauche effect is very sensitive to solvent effects, due to the large difference in polarity between the two conformers.For example, 2,3-dinitro-2,3-dimethylbutane, which in the solid state exists only in the gauche conformation, prefers the gauche conformer in benzene solution by a ratio of 79:21, but in carbon tetrachloride, it prefers the anti conformer by a ratio of 58:42. [9]
One category of reactions under Curtin–Hammett control includes transformations in which the more stable conformer reacts more quickly. This occurs when the transition state from the major intermediate to its respective product is lower in energy than the transition state from the minor intermediate to the other possible product.
When two fluorine atoms are in vicinal (i.e., adjacent) carbons, as in 1,2-difluoroethane (H 2 FCCFH 2), the gauche conformer is more stable than the anti conformer—this is the opposite of what would normally be expected and to what is observed for most 1,2-disubstituted ethanes; this phenomenon is known as the gauche effect. [9]
The chair conformation of six-membered rings have a dihedral angle of 60° between adjacent substituents thus usually making it the most stable conformer. Since there are two possible chair conformation steric and stereoelectronic effects such as the anomeric effect, 1,3-diaxial interactions, dipoles and intramolecular hydrogen bonding must be taken into consideration when looking at relative ...
Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of many conformers of comparable energy". The boat-chair conformation (below) is the most stable form. [4] This conformation was confirmed by Allinger and co-workers. [5] The crown conformation (below) [6] is
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.