Abstract
The torsional angles in 30 N-substituted benzamides and related
compounds have been estimated by the use of the 13C substituent
chemical shifts of the meta and para carbon
atoms. Steric interaction between the N-substituted
groups and the ortho
hydrogen atoms of the benzene ring is the major determinant of non-planarity in
these systems. A linear relationship between steric substituent constants of
the N-substituted groups of some
benzamides and the torsional angles is proposed. Dynamic processes involving rotation
about the C-N bond, nitrogen inversion and ring inversion contribute a dynamic
steric effect to the overall steric interaction. The preferred conformations of
some N-substituted groups is also
discussed.
Cited by
27 articles.
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