The effects of σC—Se–π hyperconjugation in 1-methoxy- and 1-nitro-4-[(phenylselanyl)methyl]benzene

Abstract

The structures of 1-methoxy-4-[(phenylselanyl)methyl]benzene, C14H14OSe, (1), and 1-nitro-4-[(phenylselanyl)methyl]benzene, C13H11NO2Se, (2), were determined at 130 K. The two structures, which differ in that (1) contains an electron-rich aromatic ring and (2) contains an electron-deficient aromatic ring, both adopt conformations which allow for σC—Se–π hyperconjugation. However, although there are significant differences in the77Se chemical shifts for these two compounds, they do not display significantly different H2C—Se or H2C—Carbond lengths, suggesting that the effects of σC—Se–π hyperconjugation in (1) and (2) are not strong enough to be manifested in measurable differences in the structural parameters.