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The existence of specific conformations is due to hindered rotation around sigma bonds, although a role for hyperconjugation is proposed by a competing theory. The importance of energy minima and energy maxima is seen by extension of these concepts to more complex molecules for which stable conformations may be predicted as minimum-energy forms.
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]
In everyday language, and often in materials science, a chemical substance is said to be "stable" if it is not particularly reactive in the environment or during normal use, and retains its useful properties on the timescale of its expected usefulness. In particular, the usefulness is retained in the presence of air, moisture or heat, and under ...
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.
In 1,2-difluoroethane, the gauche conformation is more stable than the anti conformation by 2.4 to 3.4 kJ/mole in the gas phase. This effect is not unique to the halogen fluorine, however; the gauche effect is also observed for 1,2-dimethoxyethane. A related effect is the alkene cis effect. For instance, the cis isomer of 1,2-difluoroethylene ...
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 Curtin–Hammett principle is a principle in chemical kinetics proposed by David Yarrow Curtin and Louis Plack Hammett.It states that, for a reaction that has a pair of reactive intermediates or reactants that interconvert rapidly (as is usually the case for conformational isomers), each going irreversibly to a different product, the product ratio will depend both on the difference in ...
Though butadienes are typically more stable in the s-trans conformation, for most cases energy difference is small (~2–5 kcal/mol). [ 26 ] A bulky substituent at the C2 or C3 position can increase reaction rate by destabilizing the s- trans conformation and forcing the diene into the reactive s- cis conformation. 2- tert -butyl-buta-1,3-diene ...