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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]
To name conformations of pyranose, first the conformer is determined. The common conformers are similar to those found in cyclohexane, and these form the basis of the name. Common conformations are chair (C), boat (B), skew (S), half-chair (H) or envelope (E). The ring atoms are then numbered; the anomeric, or hemiacetal, carbon is always 1 ...
Eclipsed conformation (image right in Newman projection) Staggered conformation. In chemistry an eclipsed conformation is a conformation in which two substituents X and Y on adjacent atoms A, B are in closest proximity, implying that the torsion angle X–A–B–Y is 0°. [1]
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 two conformers interconvert rapidly through nitrogen inversion ; the free energy activation barrier for this process, estimated at 6.1 kcal/mol, is substantially lower than the 10.4 kcal/mol for ...
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 ...
Such a resonance structure is called a Clar structure. In other words, a polycyclic aromatic hydrocarbon with a given number of π-sextets is more stable than its isomers with fewer π-sextets. [1] [2] In 1984, Glidewell and Lloyd provided an extension of Clar's rule to polycyclic aromatic hydrocarbons containing rings of any size. [3]
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.