An introduction to the kinetics of the triethylamine-mediated selenocyclofunctionalization of 4-pentenoic acid

Abstract

© 2018 Elsevier B.V. The aim of this work is exploration of kinetic, thermodynamic and mechanistic aspects of triethylamine-mediated selenocyclofunctionalization of 4-pentenoic acid by means of phenylselenyl halides (PhSeCl and PhSeBr). The kinetics and mechanism for these reactions have been investigated by the UV–Vis spectrophotometry. The rate constants, as well as thermodynamic parameters (ΔH≠, ΔS≠) have been determined using UV–Vis method at three different temperatures (288, 298 and 308 K) in THF as a solvent. All studied reactions gave negative values for entropy of activation, which is in agreement with the SN2 mechanism of substitution. In addition, obtained values for the rate constants have indicated the higher reactivity of PhSeCl as reagent for cyclization.