Structure of 1,6-Bis(p-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene: A Compound with a Highly Electrophilic N-Acetyl Group

Article abstract of DOI:10.1021/jo00342a032

The crystal structure of title compound (1) shows it to consist of two planar halves, related by C₂ symmetry, in which an extremely long N to acetyl bond (1.403 Angstroem) and a short carbonyl bond (1.200 Angstroem) are the most striking features.These bond lengths, and unusually high carbonyl stretching frequency (1755, 1742 cm^-1), point to strong electrophilic character in the acetyl group of 1.Acetylation by 1 of variety of aliphatic amines occurs cleanly and with a selectivity which is based on both steric factors and amine basicity.Acetates are formed from alkoxides or phenoxides.