http://www.cnr.it/ontology/cnr/individuo/prodotto/ID47380
Uncommon aqueous media for nitrilimine cycloadditions. II. Computational study of the effect of water on reaction rate (Articolo in rivista)
- Type
- Label
- Uncommon aqueous media for nitrilimine cycloadditions. II. Computational study of the effect of water on reaction rate (Articolo in rivista) (literal)
- Anno
- 2002-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1039/b205071d (literal)
- Alternative label
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Ponti A., Molteni G. (literal)
- Pagina inizio
- Pagina fine
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
- Rivista
- Note
- ISI Web of Science (WOS) (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
- Istituto di Scienze e Tecnologie Molecolari, Consiglio Nazionale delle Ricerche, via Golgi 19,
20133, Milano, Italy. E-mail: ponti@istm.cnr.it; Fax: +39 02 5031 4300
Universita` degli Studi di Milano, Dipartimento di Chimica Organica e Industriale, via Golgi 19,
20133, Milano, Italy (literal)
- Titolo
- Uncommon aqueous media for nitrilimine cycloadditions. II. Computational study of the effect of water on reaction rate (literal)
- Abstract
- The effect of water on the 1,3-dipolar cycloaddition reaction of nitrilimines to alkenes has been studied by HF
and DFT ab initio calculations. As solvation models we used the polarizable continuum model and a model
comprising small clusters consisting of reactants hydrogen-bonded to water molecules. In addition, a
combination of these two models was considered. Reactivity has been qualitatively estimated by the familiar
frontier molecular orbital approach and quantitatively computed by a recent extension to the hard-soft
acid-base principle involving molecular reactivity indices. The main conclusions drawn from the extensive
computational results are that (i) the effect of water is in general rather small and (ii) therefore, water is not
directly responsible for the large acceleration of the 1,3-dipolar cycloaddition reaction of nitrilimines to alkenes.
Its role is surely minor with respect to that played by the ionic catalysts present in the reaction mixture, in
agreement with the conclusions drawn in the experimental companion paper. (literal)
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- Autore CNR
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