F. Stunnenberg, H. Cerfontain, A. Terpstra
Sep 2, 2010
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Recueil des Travaux Chimiques des Pays-Bas
Abstract
The experimental (PES) and calculated (MNDO) ionization potentials of the three geometric isomers of 3,3,4,4-tetramethyl-1,2-bis(methoxyimino)cyclobutane [E,E)-, (E,Z)- and (Z,Z)-1] are reported. The derived electronic structures are compared with those of the three isomeric five-membered ring homologues 2. The three different orientations of the two methoxy groups in 1 have only a small effect on the energy of the π levels since the three isomers of 1 are planar [or, as in the (Z, Z)-isomer, almost so], but they have a significant effect on the order of the n+ and n− levels. The variations in the lone-pair order are discussed in terms of through-bond and through-space interactions.