Theoretical study of solvent effects on 1, 3-dipolar cycloaddition reaction

الملخص EN

In the present study the regression analysis of the rate constant k 15with solvent parameters, for two sets of 1,3-dipolarcycloaddition reactions were done.

The first was the reaction azomethine 1 with cyclooctyne 2, ynamine 3 and dimethyl acetylenecarboxylate (4) in different nonprotic solvents.

The second were the reactions of the nitrones 5 and 6 with dipolarophile 7.

Semiempirical calculations (PM3) were done for the reactants.

The resulting quantum descriptors HOMO-LUMO and the transition state quantum descriptors (LUMOdipolarophile - HOMOdipole (HdL) and LUMOdipole – HOMOdipolarophile (LdH)) were plotted against solvent parameters, in order to obtain predictive computational models.

Good to excellent correlations were obtained for these reactions.

The multiparameteric models obtained were corrected for collinearity by using Ridge regression.