Molecular mechanics (MM3) study of the conformations of ethyl esters of diastereoisomeric 3-substituted 4,4,4-trichloro-2-cyano-butanoic acids

Molecular mechanics calculation (MM3 force field) were used to study the conformations of diastereoisomeric pairs of ethyl esters of 3-substituted 4,4,4-trichloro-2-cyano-butanoic acids in order to test an assumption from 1H NMR spectra about their preferred conformations. On the basis of the most probable preferred conformation in each case, an assignment of the relative configurations of these newly synthesized compounds was made in the earlier study. The present computed most favorable conformations are in accord with the earlier qualitative considerations in all cases, thus validating the assignment of the configurations of the diastereoisomers made previously.