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

Abstract EN

The correlation between solvents parameters and rate constant (k) of 1,3-dipolar cycloaddition of benzonitrile oxide and N-ethylmaleimideorcyclopentene (k collected from literature) in different hydroxylic and non hydroxylic solvents were studied.

Single parameter correlations were found to be poor (R2 < 0.9) except for ϭ* and α ; R2 = 0.903, 0.914 respectively.

Avery good multiparameters correlation was found for the reaction of N-ethylmaleimide (logk = -0.145 + 0.719 + 0.0336 ET (30) + 0.844α ; R2 = 0.995.sig : = 0.091, F = 65.131.

While excellentdual parametric correlation was shown when the dipolarophile was cyclopentene (logk = -0.0721, -0.895α -0.0148B ;) R2 = 0.999, sig : = 0.035, F = 412.438.

Which strongly indicates that protic solvents (HBD solvents) facilitate reactions with HBA dipolarophiles.

These results may be useful as priori predictions for these reactions.