Benzylideneaniline. I. Structure and Ultraviolet Absorption Spectrum of Benzylideneaniline

The ultraviolet absorption spectra of benzylideneanilines, as well as of their conjugate acids, have been measured. These spectra can not be explained with the ever believed stilbene-type planar structures of these molecules. An alternative structure is proposed for benzylideneaniline with the benzene ring of aniline part nearly perpendicular to the rest of the molecule. This structure also adequately explains many experimental evidences, which have been investigated previously but are not accounted for by the planar structure.