Electrophilic substitution reactions of thiophene and thieno[2,3-<i>b</i>]thiophene heterocycles: a DFT study-Reference-Cited by-同舟云学术

Electrophilic substitution reactions of thiophene and thieno[2,3-b]thiophene heterocycles: a DFT study

Published:2023-06-02 Issue:7 Volume:95 Page:799-807
ISSN:0033-4545
Container-title:Pure and Applied Chemistry
language:en
Short-container-title:

Author:

Savoo Nandini¹^ORCID,Mungur Chahlaa¹,Rhyman Lydia¹²,Ramasami Ponnadurai¹²,Joule John A.³

Affiliation:

1. Computational Chemistry Group, Department of Chemistry, Faculty of Science , University of Mauritius , Réduit 80837 , Mauritius

2. Centre of Natural Product Research, Department of Chemical Sciences , University of Johannesburg , Doornfontein Campus , Johannesburg 2028 , South Africa

3. Department of Chemistry , The University of Manchester , Manchester M13 9PL , UK

Abstract

Abstract We determined the most preferred site for the electrophilic aromatic substitution (SEAr) reactions of thiophene 1 and thieno[2,3-b]thiophene 2 using the N-chlorosuccinimide electrophile in the gas phase and in acetic acid. The B3LYP/6-311G(d), B3LYP-D3/6-311G(d) and M06-2X/6-311G(d) methods were employed to investigate the SEAr reaction mechanisms. We found that, compared to the β-carbon atom, the α-carbon atom in both 1 and 2 is preferred for electrophilic attack both kinetically and thermodynamically.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/pac-2022-1104/pdf

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