Počet záznamů: 1

Does 2-Methylacetophenone Comply with Steric Inhibition of Resonance? A Direct Experimental Proof of Its Nonplanar Conformation from a Joint Ab Initio/Electron Diffraction Analysis

  1. 1.
    0355541 - UACH-T 2011 RIV US eng J - Článek v odborném periodiku
    Hnyk, Drahomír - Samdal, S. - Exner, Otto - Wann, D. A. - Rankin, D. W. H.
    Does 2-Methylacetophenone Comply with Steric Inhibition of Resonance? A Direct Experimental Proof of Its Nonplanar Conformation from a Joint Ab Initio/Electron Diffraction Analysis.
    Journal of Organic Chemistry. Roč. 75, č. 15 (2010), s. 4939-4943 ISSN 0022-3263
    Grant ostatní: EPSRC(GB) EP/F037317
    Výzkumný záměr: CEZ:AV0Z40320502; CEZ:AV0Z40550506
    Klíčová slova: substituted benzoic-acids * nuclear-magnetic-resonance * gas-phase
    Kód oboru RIV: CA - Anorganická chemie
    Impakt faktor: 4.002, rok: 2010

    The GED results, supported by the calculations that involve long-range correlation, are in a good agreement with C-13 NMR spectroscopic investigations, UV spectra, and dipole moment studies. However, previous claims that assumed steric inhibition of resonance caused by a significantly nonplanar conformation with phi close to 90 degrees have been disproved. Steric crowding is evident from the geometrical parameters, particularly from the C(1)-C(2) bond length and from the C(1)-C(2)-C(H-3) and C(2)-C(1)-C(O) bond angles. It is concluded that any explanation of reactivity by steric inhibition of resonance and by other steric factors must be supported by experimental and/or theoretical investigation of the actual molecular shape.
    Trvalý link: http://hdl.handle.net/11104/0194288