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Low temperature 13C NMR study of 1-(3-pentyloxyphenylcarbamoyloxy)-2-dialkyl- aminocyclohexanes

✍ Scribed by V. Mlynárik; L. Beneš

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
209 KB
Volume
14
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Cyclohexane and piperidine ring reversal in 1‐(3‐pentyloxyphenylcarbamoyloxy)‐2‐dialkylaminocyclohexanes was investigated by ^13^C NMR. An unusually low conformational energy Δ__G__ = 0.59 kJ mol^−1^ and activation parameters Δ__G__^≠^~218~ = 43.8 ± 0.4 kJ mol^−1^, Δ__H__^≠^ = 48.9 ± 2.5 kJ mol^−1^ and Δ__S__^≠^ = 23 ± 9 J mol^−1^ K^−1^ were found for the diequatorial to diaxial transition of the cyclohexane ring in the trans‐pyrrolidinyl derivative. In the trans‐piperidinyl derivative, Δ__G__~222~ = 44.7 ± 0.5 KJ mol^−1^, Δ__H__^≠^ = 55.7 ± 6.3 kJ mol^−1^ and Δ__S__^≠^ = 51 ± 21 J mol^−1^ K^−1^ was found for the piperidine ring reversal from the non‐equivalence of the α‐carbons.

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