The effects of σc - Se-π hyper-conjugation in 1-meth-oxy- and 1-nitro-4-[(phenyl-selan-yl)meth-yl]benzene

Abstract

The structures of 1-meth-oxy-4-[(phenyl-selan-yl)meth-yl]ben-zene, C14H14OSe, (1), and 1-nitro-4-[(phenyl-selan-yl)meth-yl]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 σ C - Se-π hyperconjugation. However, although there are sig-nificant differences in the 77Se chemical shifts for these two compounds, they do not display significantly different H2C - Se or H2C - Car bond lengths, suggesting that the effects of σ C - Se-π hyperconjugation in (1) and (2) are not strong enough to be manifested in measurable di..