Electronic interactions in triatomic cyclic compounds. Charge-transfer complexes between epoxide donors and ICl as acceptor

Abstract

Charge-transfer (c.t.) complexes between epoxide donors and ICl as acceptor have been studied spectrophotometrically. It was found that the basicity in the 3-, 4-, 5- and 6-membered rings depends on the size of the ring, following in the order 4 > 5 > 6 > 3 atoms. This is principally caused by the different ∠ COC bond angles and the consequent different types of hybridization of the oxygen orbitals in the various compounds.

K _ct data show that in the styrene oxides a small conjugative effect is present between the phenyl and oxiran rings. However, this classic conjugation is completely absent in both cis- and trans-stilbene oxides.