Tetrahedron p. 6241 - 6248 (1996)
Update date:2022-08-12
Topics:
Desimoni
Faita
Garau
Righetti
The effect of the solvent on the cheletropic reaction of 3,4-dimethyl-2,5-dihydrothiophen-1,1-dioxide was kinetically investigated in 14 solvents. The rate constants of the forward reaction as well as those of the reverse process and the corresponding equilibrium constants were found to be linearly correlated with the E(T)(30) solvent polarity parameters. The solvent effect can be interpreted in terms of change of polarity during the activation process. The different response of the forward and reverse process to the increase of solvent polarity pointed out a clear difference between pericyclic reactions characterized by non-specific solvent effects and those whose medium effect is determined by the specific interaction between the FMO of solute and solvent.
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