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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
- 1.0355541 - ÚACH 2011 RIV US eng J - Journal Article
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. E-ISSN 1520-6904
Grant - others:EPSRC(GB) EP/F037317
Institutional research plan: CEZ:AV0Z40320502; CEZ:AV0Z40550506
Keywords : substituted benzoic-acids * nuclear-magnetic-resonance * gas-phase
Subject RIV: CA - Inorganic Chemistry
Impact factor: 4.002, year: 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.
Permanent Link: http://hdl.handle.net/11104/0194288
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