Theoretical investigations of 1,4‐butanediol and 2‐butene‐1,4‐diol cyclodehydration using postprocessing visualization of quantum chemical calculation data

Abstract

ABSTRACT:Cyclodehydration of 1,4-butanediol and 2-butene-1,4-diol to the corresponding cyclic ethers was studied using the AM1 semiempirical method. It was established that the cyclodehydration reaction of 1,4-butenediol and 2-butene-1,4-diol is effected by converting of semicyclic conformers in the presence of acidic and basic active centers. The calculation results indicate that a concerted mechanism is probably realized in the cyclodehydration of both diols, while the sequences of the predicted steps in the cyclodehydration reaction for 1,4-butanediol and 2-butene-1,4-diol are different. The calculated reaction heats for 1,4-butanediol and 2-butene-1,4-diol transformations are Ϫ184.029 and Ϫ308.746 kcal/mol, respectively.