A DFT investigation of base-catalyzed beta-elimination reactions in water solution for systems activated by the pyridine ring: Theory vs. experiment (Articolo in rivista)

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  • A DFT investigation of base-catalyzed beta-elimination reactions in water solution for systems activated by the pyridine ring: Theory vs. experiment (Articolo in rivista) (literal)
Anno
  • 2008-01-01T00:00:00+01:00 (literal)
Alternative label
  • Mosconi, E.; De Angelis, F.; Tarantelli, F.; Alunni, S.; Sgamellotti, A. (2008)
    A DFT investigation of base-catalyzed beta-elimination reactions in water solution for systems activated by the pyridine ring: Theory vs. experiment
    in Chemical physics letters (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Mosconi, E.; De Angelis, F.; Tarantelli, F.; Alunni, S.; Sgamellotti, A. (literal)
Pagina inizio
  • 100 (literal)
Pagina fine
  • 107 (literal)
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  • 460 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#note
  • DOI: 10.1016/j.cplett.2008.05.055 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Titolo
  • A DFT investigation of base-catalyzed beta-elimination reactions in water solution for systems activated by the pyridine ring: Theory vs. experiment (literal)
Abstract
  • We report a theoretical investigation of beta-elimination reactions in systems activated by the pyridine ring. The investigated reaction, the acetohydroxamate-induced beta-elimination in protonated N-[ 2-(2-pyridyl) ethyl] quinuclidinium, offers a unique opportunity to test computational methodologies since detailed kinetic experimental data are available. We calculated the pK(a)s of the acetohydroxamic acid and the substrate and thoroughly characterized the reactive free-energy profile. The reaction proceeds via a stable carbanion intermediate. Except a discrepancy in the reproduction of the pK(a)s of the acetohydroxamic acid, the calculated free-energy profile is in excellent agreement with the experiment, showing the general reliability of the present approach. (C) 2008 Elsevier B. V. All rights reserved. (literal)
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