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A proton magnetic resonance study of the conformation of the seven‐membered ring in benzocycloheptene
Author(s) -
StJacques Maurice,
Vaziri Cambyse
Publication year - 1972
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270040110
Subject(s) - ring (chemistry) , cyclohexane , coupling constant , chemistry , cyclohexane conformation , coupling (piping) , computational chemistry , stereochemistry , hydrogen bond , physics , molecule , quantum mechanics , organic chemistry , materials science , metallurgy
The computer analysis of the PMR spectra of several partially deuterated benzocycloheptene derivatives at −120° provides values for all the coupling constants about the C 3 C 4 bond. An interpretaion using the Karplus equation shows unambiguously that the seven‐membered ring exists as a chair conformation. The relationship between the coupling constants determined shows that the form of the Karplus equation established empirically for cyclohexane is applicable to this seven‐membered ring. A comparison of coupling constants shows that the benzocycloheptene chair is more puckered than the cyclohexane chair.