QUANTUM-CHEMICAL STUDY OF THE REACTION MECHANISM 1,2-ETHANEDIIOL WITH 1,3-DICHLOROPROPENE
Rubrics: CHEMISTRY AND CHEMICAL TECHNOLOGY
Authors:
2.
Russian Federation
Type:
Article
Pages:
from 56
to 57
Status:
Published
Received:
12.03.2020
Accepted:
05.06.2020
Published:
05.06.2020
Subject area:
GRNTI 31.01 Общие вопросы химии
OKSO 04.06.01 Химические науки
OKSO 04.06.01 Химические науки
Language:
Russian
Keywords:
1,2-ethanedithiol, 1,3-dichloropropene, reaction mechanism, nucleophilic substitution, prototropic allyl rearrangement, theory of the electron density functional, B3LYP, potential energy surface.
Abstract (English):
The theoretical mechanism of the interaction of 1,3-dichloropropene with 1,2- ethanedithiol in the system "hydrazine hydrate-KOH" has been proposed by the method of B3LYP / 6- 311 ++ G (d, p) in the framework of the theory of the electron-density functional according to which the reaction proceeds successively in several stages, including the nucleophilic substitution of the chlorine atom present in the sp3-hybridized carbon atom with a sulfur atom to form a mono-substitution product that undergoes a prototropic allylic rearrangement that migrates the double bond to the sulfur atom, followed by closure in the dithiolane cycle due to the nucleophilic attack of the sulfide anion of the second thiol group of the reagent per carbon atom located in the γ-position with respect to the second chlorine atom.
The theoretical mechanism of the interaction of 1,3-dichloropropene with 1,2- ethanedithiol in the system "hydrazine hydrate-KOH" has been proposed by the method of B3LYP / 6- 311 ++ G (d, p) in the framework of the theory of the electron-density functional according to which the reaction proceeds successively in several stages, including the nucleophilic substitution of the chlorine atom present in the sp3-hybridized carbon atom with a sulfur atom to form a mono-substitution product that undergoes a prototropic allylic rearrangement that migrates the double bond to the sulfur atom, followed by closure in the dithiolane cycle due to the nucleophilic attack of the sulfide anion of the second thiol group of the reagent per carbon atom located in the γ-position with respect to the second chlorine atom.
Keywords:
1,2-ethanedithiol, 1,3-dichloropropene, reaction mechanism, nucleophilic substitution, prototropic allyl rearrangement, theory of the electron density functional, B3LYP, potential energy surface.
1,2-ethanedithiol, 1,3-dichloropropene, reaction mechanism, nucleophilic substitution, prototropic allyl rearrangement, theory of the electron density functional, B3LYP, potential energy surface.
1. Levanova E.P., Nikonova V.S., Albanov A.I., Rozencveyg I.B., Korchevin N.A. Sintez 2-propiliden-1,3-ditiolana iz 1,3-dihlorpropena i 1,2- etanditiolyata // ZhOpH. 2016. T. 52.
