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Ring distortion effect on δ 13 C values of bicyclo[4. n .0] alkanes
Author(s) -
Metzger P.,
Cabestaing C.,
Casadevall E.,
Casadevall A.
Publication year - 1982
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.1270190307
Subject(s) - cyclohexane , ring (chemistry) , bicyclic molecule , chemistry , ring size , ring strain , distortion (music) , cyclohexane conformation , stereochemistry , cycloalkane , chemical shift , crystallography , materials science , molecule , organic chemistry , hydrogen bond , catalysis , amplifier , optoelectronics , cmos
The 13 C NMR spectra of trans ‐ and cis ‐fused bicyclo[4. n .0]alkanes, where n =4, 3 and 2, were determined. The distortion of the six membered ring, which is due to the strain arising from the 1,2 fusion of cyclohexane with a smaller ring, is apparent mainly for the chemical shifts of the ring junction carbons. Both for the trans ‐and for the cis ‐fused hydrocarbons the results support a cyclohexane in a chair conformation, distorted to a different degree according to the size of the other ring. The geometries of the different compounds in the series were calculated.