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The effects of σC—Se–π hyperconjugation in 1‐methoxy‐ and 1‐nitro‐4‐[(phenylselanyl)methyl]benzene
Authors:Jonathan Michael White  Paul Blanc
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 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 σC—Se–π hyperconjugation in (1) and (2) are not strong enough to be manifested in measurable differences in the structural parameters.
Keywords:organoselenium compounds  hyperconjugation  low‐temperature crystallography  crystal structure  stereoelectronic effects
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