
%0 Journal Article
%A Herrmann, RI 
%A Rae, ID 
%T The effects of electronic buttressing on the conformations of some orthodisubstituted benzenes
%J Australian Journal of Chemistry
%D 1972/04/01
%V 25
%N 4
%P 811-815
%K 
%R https://doi.org/10.1071/CH9720811
%U https://www.publish.csiro.au/paper/CH9720811 
%X When one of a pair of substituents ortho to each other on a benzene ring is conjugated with an appropriate para substituent, it is pulled towards coplanarity with the aromatic ring and the other substituent has to take a greater share of the twisting necessary to avert steric conflict. This effect, termed electronic buttressing, is demonstrated in the proton magnetic resonance spectra of 5-dimethylamino-2- nitroanilines, 5-substituted methyl 2-nitrobenzoates, and 4-substituted 1,2-dinitrobenzenes. In this latter group the size of the effect is shown to depend on the conjugative ability of the 4-substituent. 
