title: The effects of σ(C-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 σ(C-Se)-π hyperconjugation. However, although there are significant differences in the (77)Se chemical shifts for these two compounds, they do not display significantly different H2C-Se or H2C-C(ar) 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 differences in the structural parameters.
authors.affiliation: School of Chemistry and BIO-21 Institute, University of Melbourne, Parkville 3010, Melbourne, Australia.
authors.forename: Jonathan Michael
authors.initials: JM
authors.lastname: White
authors.affiliation: School of Chemistry and BIO-21 Institute, University of Melbourne, Parkville 3010, Melbourne, Australia.
authors.forename: Paul
authors.initials: P
authors.lastname: Blanc
mesh_terms: D018360:Crystallography, X-Ray; D004583:Electrons; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000737:chemistry*; D011789:Quantum Theory; D018036:Selenium Compounds / Q000737:chemistry*
chemical_list: C000595615:1-methoxy-4-((phenylselanyl)methyl)benzene; C000595614:1-nitro-4-((phenylselanyl)methyl)benzene; D016566:Organoselenium Compounds; D018036:Selenium Compounds
keywords: crystal structure; hyperconjugation; low-temperature crystallography; organoselenium compounds; stereoelectronic effects