Photochemical properties and structures ofN-amino andN-azomethine derivatives of 2,4,6-triphenylpyridinium perchlorates

The molecular structures of the initial compounds and the products of photocyclization involving amino and azomethine groups in perchlorates ofN-amino (1) andN-azomethine (2) derivatives of 2,4,6-triphenylpyridinium cations were studied. Cations1 and2 have an essentially non-coplanar arrangement of the -Ph rings, and the product of photocyclization of2, cation3, is characterized by a flattened structure. It was found that the orientation of the lone electron pair of the N atom with respect to one of the planes of the -Ph rings in molecule1 is more favorable for monocyclization involving the amino group. The structure of molecule2 allows two routes of the photoreaction,viz., O N proton transfer and monocyclization with an -Ph ring. However, the structural features of molecule2 are more favorable for photocyclization.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 296–301, February, 1995.