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Substituent Effects on the n and ? Molecular Orbitals of Methanimines. Photoelectron Spectra and Electronic Structures of Some Aliphatic Non-conjugated Diimines with Implications for Their Photochemistry
Bittner, Andreas J.,Rademacher, Paul
, p. 555 - 580 (2007/10/02)
The electronic structures of methanimine (1) and all possible methyl-, trifluoromethyl-, methoxy-, fluoro-, and chloro-substituted methanimines (2) - (26) have been studied by semiempirical quantum chemical calculations with special consideration of the energies of the two highest occupied molecular orbitals.By the same methods, the non-conjugated dimines (27a) - (30c) with one to four methylene groups separating the imino functions and different numbers of methyl groups have been investigated.The linear dialdimines (31) - (33) and diketimines (34) - (36)of 1,2 diaminoethane, 1,3 diaminopropane, and 1,4 diaminobutane have been prepared and characterized.The electronic structures of these compounds have been studied by photoelectron spectroscopy and semiempirical quantum chemical calculations.Acording to these results, photochemical -cycloadditions of alkyl-substituted imines are unlikely to occur.Photolysis of the diimines (31), (32), (34), and (35) only in the presence of a Lewis acid afforded products of Norrish type I reactions.
