Conformational analysis of some 1 R ,4 S ‐2‐arylidene‐ p ‐menthan‐3‐ones by  1 H NMR spectroscopy and molecular simulation | Zendy

Pivnenko Nikolay S. | Zendy; Drushlyak Tatyana G. | Zendy; Kutulya Lidiya A. | Zendy; Vashchenko Valeriy V. | Zendy; Doroshenko Andrey O. | Zendy; Goodby John W. | Zendy

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Conformational analysis of some 1 R ,4 S ‐2‐arylidene‐ p ‐menthan‐3‐ones by 1 H NMR spectroscopy and molecular simulation

Author(s) -

Pivnenko Nikolay S.,

Drushlyak Tatyana G.,

Kutulya Lidiya A.,

Vashchenko Valeriy V.,

Doroshenko Andrey O.,

Goodby John W.

Publication year - 2002

Publication title -

magnetic resonance in chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0749-1581

DOI - 10.1002/mrc.1068

Subject(s) - chemistry , conformational isomerism , substituent , cyclohexane conformation , isopropyl , ring (chemistry) , cyclohexanone , stereochemistry , crystallography , benzene , alkyl , nuclear magnetic resonance spectroscopy , computational chemistry , molecule , medicinal chemistry , hydrogen bond , organic chemistry , catalysis

Based on 1 H NMR spectral analysis combined with molecular simulation, conformational states of the cyclohexanone ring were studied for some 1 R ,4 S ‐2‐(4‐X‐benzylidene)‐ p ‐menthan‐3‐ones (X = COOCH 3 or C 6 H 5 ) in CDCl 3 and C 6 D 6 . The co‐existence of chair conformers with an axial orientation of both alkyl substituents and twist‐boat forms was established for the compounds studied at room temperature (22–23° C). The substituent X does not influence appreciably the ratio of these conformers, but the fraction of twist‐boat forms increases noticeably in benzene solutions as compared with CDCl 3 solutions. Rotameric states of the isopropyl fragment were also characterised for the compounds studied. Distinctions in conformational states for the 1 R ,4 S ‐2‐arylidene‐ p ‐menthan‐3‐ones and (−)‐menthone were revealed and are discussed. Copyright © 2002 John Wiley & Sons, Ltd.

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