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The conformational equilibrium of the amino group

โœ Scribed by E.L. Eliel; E.W. Della; T.H. Williams

Publisher
Elsevier Science
Year
1963
Tongue
French
Weight
218 KB
Volume
4
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Williams of Notre Dame, AMONG the numerous conformational equilibrium values reported in the literature 1,2 that of the amino group is conspicuously missing. Tich;, Jon;; and Sicher3 some years ago determined pK data which indicate a qualitatively that the -dG value for the equilibrium is comparable in magnitude with that for methyl (1.7 kcal./mole4) and these indications are now quantitatively supported as shown in the accompanying letter. 5

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Studies in the field of conformational snalyeis have led to the assignment of ccnfozmational free energy differences (-AFx) to a large number of substituents.' No information has appeared on the oonfonnatlcmal equilibrium of the trifluoromethyl group, whioh is of interest caupared vith other syuveet

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## Recent investigations of a variety of substituted N-methylpiperidines indicate that the N-methyl group of g-methylpiperidine prefers the equatorial over the axial orientation by about -2.5 to 3.0 kcal/mol,1-5 a value considerably higher then that found in methylcyclohexane. 6,7 we now report on