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The staggered conformation is more stable by 12.5 kJ/mol than the eclipsed conformation, which is the energy maximum for ethane. In the eclipsed conformation the torsional angle is minimised. staggered conformation left, eclipsed conformation right in Newman projection
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]
The conformation which places the methyl group in the equatorial position is 3.16 kcal/mol more stable than the axial conformation. [7] The product ratio of 95:5 indicates that the more stable conformer leads to the major product.
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.
After much controversy during the 1950s–1970s, the equatorial conformation was found to be more stable by 0.72 kcal/mol in the gas phase. [20] In nonpolar solvents , a range between 0.2 and 0.6 kcal/mol has been estimated, but in polar solvents the axial conformer may be more stable. [ 21 ]
The most stable conformer of 1,3-butadiene is the s-trans conformation, in which the molecule is planar, with the two pairs of double bonds facing opposite directions. This conformation is most stable because orbital overlap between double bonds is maximized, allowing for maximum conjugation, while steric effects are minimized.
Due to the anomeric effect, dimethoxymethane has a preference toward the gauche conformation with respect to each of the C–O bonds, instead of the anti conformation. Since there are two C–O bonds, the most stable conformation is gauche - gauche , which is around 7 kcal/mol more stable than the anti - anti conformation, while the gauche ...
Chemical substances or states can persist indefinitely even though they are not in their lowest energy state if they experience metastability - a state which is stable only if not disturbed too much. A substance (or state) might also be termed "kinetically persistent" if it is changing relatively slowly (and thus is not at thermodynamic ...