Kinetics and mechanism of producing 3,8-dimethyl-3H-imidazo[4,5-a]acridine-11-carbonitrile: a DFT investigation

Kinetics and mechanism of producing 3,8-dimethyl-3H-imidazo[4,5-a]acridine-11-carbonitrile: a DFT... The derivatives of acridine play important roles as dyes, drugs, and antiseptics. Herein, we have investigated the kinetics and the mechanism of the formation of 3,8-dimethyl-3H-imidazo[4,5-a]acridine-11-carbonitrile as an imidazo-acridine derivative by using density functional theory. The kinetics and the mechanism of the reaction are investigated without and by considering catalytic effects of the OH−. The proposed mechanisms involve three main steps. Firstly, a tautomerization reaction occurs via an intramolecular proton transfer. Then, the intramolecular cyclization reaction creates a new six-membered ring. The final step is an intramolecular condensation reaction, which results in formation of the acridine product. Barrier energy of the reaction was significantly decreased in the OH− catalyzed pathway. In this proper pathway, the intramolecular cyclization is the rate-determining step of the reaction. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Kinetics and mechanism of producing 3,8-dimethyl-3H-imidazo[4,5-a]acridine-11-carbonitrile: a DFT investigation

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Publisher
Springer Netherlands
Copyright
Copyright © 2016 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2733-2
Publisher site
See Article on Publisher Site

Abstract

The derivatives of acridine play important roles as dyes, drugs, and antiseptics. Herein, we have investigated the kinetics and the mechanism of the formation of 3,8-dimethyl-3H-imidazo[4,5-a]acridine-11-carbonitrile as an imidazo-acridine derivative by using density functional theory. The kinetics and the mechanism of the reaction are investigated without and by considering catalytic effects of the OH−. The proposed mechanisms involve three main steps. Firstly, a tautomerization reaction occurs via an intramolecular proton transfer. Then, the intramolecular cyclization reaction creates a new six-membered ring. The final step is an intramolecular condensation reaction, which results in formation of the acridine product. Barrier energy of the reaction was significantly decreased in the OH− catalyzed pathway. In this proper pathway, the intramolecular cyclization is the rate-determining step of the reaction.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Sep 19, 2016

References

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