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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]
For example, the complex [Ni(dien) 2)] 2+ is more stable than the complex [Ni(en) 3)] 2+; both complexes are octahedral with six nitrogen atoms around the nickel ion, but dien (diethylenetriamine, 1,4,7-triazaheptane) is a tridentate ligand and en is bidentate. The number of chelate rings is one less than the number of donor atoms in the ligand.
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
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.
Hyperconjugation can be used to rationalize a variety of chemical phenomena, including the anomeric effect, the gauche effect, the rotational barrier of ethane, the beta-silicon effect, the vibrational frequency of exocyclic carbonyl groups, and the relative stability of substituted carbocations and substituted carbon centred radicals, and the thermodynamic Zaitsev's rule for alkene stability.
The structure was found, using a cluster expansion method, to be the most stable of all the possible hydrogenation ratios of graphene. [4] In 2007, researchers found that the compound is more stable than other compounds containing carbon and hydrogen, such as benzene, cyclohexane and polyethylene. [1]
In the chair conformation, the reference plane is chosen such that the lowest-numbered atom (usually C-1) is exoplanar. In the skew conformation, the plane contains three adjacent atoms and one other with the atom with the lowest possible number exoplanar. [6] Atoms above the plane are written before the conformer label, as a superscript
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 ...