Natural bond orbital analysis of hyperconjugative stabilization effects in the transition states of cyclohexanone reduction with LiAlH4

Abstract

Natural bond orbital (NBO) analysis of the transition states of cyclohexanone reduction with LiAlH₄ located at the B3LYP/6-31+G(d) level along the intrinsic reaction coordinate (IRC) strongly indicate that the antiperiplanar effect involving the incipient bond may not be important as a controlling factor of π-facial selection in carbonyl reduction.