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

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• 作者：Fatemeh Zonozi ; S. Ali Beyramabadi ; Mehdi Pordel…
• 关键词：Acridine ; DFT ; PCM ; Kinetics ; Mechanism ; Tautomerization
• 刊名：Research on Chemical Intermediates
• 出版年：2017
• 出版时间：March 2017
• 年：2017
• 卷：43
• 期：3
• 页码：1829-1846
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Catalysis; Physical Chemistry; Inorganic Chemistry;
• 出版者：Springer Netherlands
• ISSN：1568-5675
• 卷排序：43

文摘

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.