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Computational investigation of water as catalyst and solvent in aromatic nucleophilic substitution reaction of 2-bromopyridine

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Title Computational investigation of water as catalyst and solvent in aromatic nucleophilic substitution reaction of 2-bromopyridine
 
Creator Singh, Harjinder
 
Subject DFT studies
Nucleophilic substitution
QTAIM
RDG
FMO
 
Description 999-1007
We have computationally investigated the role of water as a catalyst and solvent in the aromatic nucleophilic substitution
reaction of 2-bromopyridine with thiophenol. Water as catalyst significantly lowers the transition state energy by an amount
of 5.58 kcal/mol via forming hydrogen bonds with reactants and the transition state. The role of water as catalyst is further
studied by investigating non-covalent interactions. Results show that water forms hydrogen bonding with reactant
2-bromopyridine (–5.90 kcal/mol) and two hydrogen bonds in the transition state (7.24 and 7.95 kcal/mol) that stabilize the
transition state. Reduced density gradient analysis confirms these interactions. Frontier molecular orbital analysis shows
water reduces the energy gap in both reactants and transition states thus lowering the reaction’s energy requirement.
Additionally, the reaction’s energy requirement in water is 1.25 kcal/mol lower than in non protic solvent DMSO, further
confirming water’s dual role as a catalyst and solvent.
 
Date 2024-10-23T10:08:42Z
2024-10-23T10:08:42Z
2024-10
 
Type Article
 
Identifier 2583-1321 (Online); 0019-5103 (Print)
http://nopr.niscpr.res.in/handle/123456789/64737
https://doi.org/10.56042/ijc.v63i10.12215
 
Language en
 
Publisher NIScPR-CSIR, India
 
Source IJC Vol.63(10) [October 2024]