The effect of the electrophilic group on the hierarchy of nucleofuges in the aminolysis reactions of thiol- and dithiocarbonates with secondary alicyclic amines: A kinetic and theoretical study-Reference-Cited by-同舟云学术

The effect of the electrophilic group on the hierarchy of nucleofuges in the aminolysis reactions of thiol- and dithiocarbonates with secondary alicyclic amines: A kinetic and theoretical study

Published:2019 Issue:16 Volume:43 Page:6372-6379
ISSN:1144-0546
Container-title:New Journal of Chemistry
language:en
Short-container-title:New J. Chem.

Author:

Montecinos Rodrigo¹²³⁴^ORCID,Gazitúa Marcela¹²³⁴^ORCID,Santos José G.¹²³⁴^ORCID

Affiliation:

1. Facultad de Química y de Farmacia

2. Pontificia Universidad Católica de Chile

3. Santiago 6094411

4. Chile

Abstract

Thiol- and dithiocarbonates react with amines, forming tetrahedral intermediates and then different product ratios. Theoretical results show that the product ratio depends on the water microsolvation of the electrophilic group in the anionic intermediate.

Funder

Fondo Nacional de Desarrollo Científico y Tecnológico

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,General Chemistry,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2019/NJ/C9NJ00385A

Reference34 articles.

1. Kinetics and Mechanisms of Reactions of Thiol, Thiono, and Dithio Analogues of Carboxylic Esters with Nucleophiles

2. Kinetics and mechanism of the aminolysis of O-ethyl S-aryl dithiocarbonates in acetonitrile

3. Kinetics and mechanism of the aminolysis of bis(4-nitrophenyl) carbonate andO-(4-nitropheny) S-(4-nitrophenyl) thio and dithiocarbonate

4. Experimental and theoretical studies on the nucleofugality ratio in the aminolysis reactions of O-(4-cyanophenyl) O-(3-nitrophenyl) thionocarbonate with amines in aqueous ethanol

5. Experimental and Theoretical Studies on the Nucleofugality Patterns in the Aminolysis and Phenolysis of S-Aryl O-Aryl Thiocarbonates

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