QUANTUM-CHEMICAL STUDY OF THE MECHANISM OF REACTION OF BENZOELACETHYLENE WITH DISELENOMALONAMIDE
Rubrics: CHEMISTRY AND CHEMICAL TECHNOLOGY
Authors:
Type:
Article
Pages:
from 89
to 90
Status:
Published
Received:
08.06.2020
Accepted:
06.01.2023
Published:
16.06.2020
Subject area:
GRNTI 31.01 Общие вопросы химии
Language:
Russian
Keywords:
benzoyl acetylene, dyselenomalonamide, reaction mechanism, nucleophilic substitution, electron density functional theory, B3LYP, potential energy surface
Abstract (English):
According to the results of a quantum chemical study in the framework of the electron density functional theory using the В3LYP/6-311++G (d, p) method, a theoretical mechanism of the reaction of benzoylacetylene with dyselenomalonamide is proposed. It was shown that the reaction includes the following stages: nucleophilic addition of the selenoamide fragment to the electrondeficient -carbon atom of benzoylacetylene with the formation of ketovinyl selenide and further intramolecular cyclization of the mono-derivative due to nucleophilic addition of the second selenium atom of the selenol group of the reagent via the same -carbon with the formation of a heterocyclic product.
According to the results of a quantum chemical study in the framework of the electron density functional theory using the В3LYP/6-311++G (d, p) method, a theoretical mechanism of the reaction of benzoylacetylene with dyselenomalonamide is proposed. It was shown that the reaction includes the following stages: nucleophilic addition of the selenoamide fragment to the electrondeficient -carbon atom of benzoylacetylene with the formation of ketovinyl selenide and further intramolecular cyclization of the mono-derivative due to nucleophilic addition of the second selenium atom of the selenol group of the reagent via the same -carbon with the formation of a heterocyclic product.
Keywords:
benzoyl acetylene, dyselenomalonamide, reaction mechanism, nucleophilic substitution, electron density functional theory, B3LYP, potential energy surface
benzoyl acetylene, dyselenomalonamide, reaction mechanism, nucleophilic substitution, electron density functional theory, B3LYP, potential energy surface
1. Nizovtseva T.V., Komarova T.N., Nakhmanovich A.S., Larina L.I., Lopyrev V.A., Kalistratova E.F. Reaction of dithiomalonamide and dianilide with α-acetylene ketones // Russ J. Org. Chem. 2002. V. 38. R. 1205-1207.
