Abstract
Ab initio calculations employing both minimal (STO–4G) and split valence (4–31G) basis sets have been used to study the conformational energy surface of N‐benzylideneaniline (NBA). The former indicate that the minimum energy conformation of NBA corresponds to a rotation about the N–phenyl bond of ≊ 45° and a rotation about the CH–phenyl bond of 0°. These results are in close correspondence with those from spectroscopic and x‐ray diffraction studies. This represents a significant improvement over the results obtained from most semiempirical methods which in general have not been able to account for the rotation about the exocyclic bonds. The compounds N‐ethylideneaniline and N‐methylbenzylidenimine were also studied and found to be good models for determining the energetics about the two exocyclic single bonds using both the minimal and extended (4‐31G) basis sets. A partitioning of the results for these two model compounds yields information which permits an analysis of the origin of the barrier to a plan...
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