DFT-HSAB Prediction of Regioselectivity in 1,3-Dipolar Cycloadditions: Behaviour of (4-Substituted)benzonitrile Oxides towards Methyl Propiolate (Articolo in rivista)

Type
Label
  • DFT-HSAB Prediction of Regioselectivity in 1,3-Dipolar Cycloadditions: Behaviour of (4-Substituted)benzonitrile Oxides towards Methyl Propiolate (Articolo in rivista) (literal)
Anno
  • 2006-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/chem.200500739 (literal)
Alternative label
  • Ponti A., Molteni G. (2006)
    DFT-HSAB Prediction of Regioselectivity in 1,3-Dipolar Cycloadditions: Behaviour of (4-Substituted)benzonitrile Oxides towards Methyl Propiolate
    in Chemistry - A European Journal
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Ponti A., Molteni G. (literal)
Pagina inizio
  • 1156 (literal)
Pagina fine
  • 1161 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 12 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • [a] Dr. A. Ponti Consiglio Nazionale delle Ricerche Istituto di Scienze e Tecnologie Molecolari via Golgi 19, 20133 Milano (Italy) Fax: (+39) 02-5031-4300 E-mail: alessandro.ponti@istm.cnr.it [b] Dr. G. Molteni UniversitF degli Studi di Milano, Dipartimento di Chimica Organica e Industriale via Venezian 21, 20133 Milano (Italy) [**] HSAB=hard-soft acid-base principle (literal)
Titolo
  • DFT-HSAB Prediction of Regioselectivity in 1,3-Dipolar Cycloadditions: Behaviour of (4-Substituted)benzonitrile Oxides towards Methyl Propiolate (literal)
Abstract
  • The regioselectivity of 1,3-dipolar cycloadditions between (4-substituted)benzonitrile oxides and methyl propiolate cannot be rationalized on the basis of the electron demand of the reactants or frontier molecular-orbital theory. To this problem, we have applied a quantitative formulation of the hard-soft acid-base principle developed within the density functional theory. Global and local reactivity indices were computed at B3LYP/6-311+G(d,p) level. The details of charge transfer upon the reactive encounter have been elucidated, and the computed regioselectivity has been shown to be in good agreement with experimental data. (literal)
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