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The conformations of bicyclo[3.1.0]hexane derivatives by 1 H and 13 C NMR
Author(s) -
Rees John C.,
Whittaker David
Publication year - 1981
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.1270150410
Subject(s) - dihedral angle , substituent , bicyclic molecule , ring (chemistry) , buckle , chemistry , twist , crystallography , stereochemistry , materials science , geometry , organic chemistry , molecule , mathematics , hydrogen bond , composite material
The 1 H and 13 C spectra of bicyclo[3.1.0]hexanes and thujanes have been recorded and assigned. Application of the Karplus equation has yielded dihedral angles, and a computer calculation of the angle of ring buckle as a function of the main dihedral angles has been carried out. The calculated angles of ring buckle agree well with known values in the bicyclo[3.1.0]hexanes, but for 1‐methylbicyclo[3.1.0]hexanes and thujanes the results are not self consistent. It is suggested that the bridgehead substituent causes the boat to twist, although the twist can be reduced by an axial methyl substituent on C‐4.