Solvent effect as the result of frontier molecular orbital interaction-1 : The diels-alder reaction between 1,4-naphthoquinone and 2,3-dimethylbutadiene |
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| Authors: | A Corsico Coda G Desimoni E Ferrari PP Righetti G Tacconi |
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| Institution: | Dipartimento di Chimica Organica dell''Università di Pavia, Viale Taramelli 10, I-27100 Pavia Italy |
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| Abstract: | A kinetic investigation of the solvent effect in the Diels-Alder reaction of2,3-dimethylbutadiene and 1,4-naphthoquinone was undertaken and a hyperbolic correlation was obtained with the Acceptor Numbers (AN) of the solvent. Since ANs correlate with the LUMO of the solvent, the results can be rationalized in terms of an interaction between the LUMO of the solvent and the HOMO of the quinone which determines the MO energy of the solvated quinone. This rationalization seems useful when reactants, products and transition state are weakly polar. |
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