Halogenating and nitrating activity of reagents based on sodium nitrate and alkali metal halides in acetic acid

V. D. Filimonov, Yulia Yurievna Miroshnichenko, M. S. Yusubov, I. A. Perederina, Ki Whan Chi, O. Kh Poleshchuk

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Abstract

Alkali metal halides NaF, KCl, and KBr sharply enhance the nitrating activity of sodium nitrate in acetic acid with respect to 9-methylcarbazole. In the presence of KI and KBr, both nitration and halogenation of the substrate occurs, while KCl and NaF promote only the nitration process. The results may be interpreted in terms of formation of the corresponding nitryl halides XNO2 (X = F, Cl, Br, I) whose structure and reactivity were examined in the framework of the density functional theory (DFT B3LYP/3-21G*).

Original language	English
Pages (from-to)	917-923
Number of pages	7
Journal	Russian Journal of Organic Chemistry
Volume	40
Issue number	7
DOIs	https://doi.org/10.1023/B:RUJO.0000045178.33131.c2
Publication status	Published - 1 Jul 2004

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ASJC Scopus subject areas

Organic Chemistry

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Filimonov, V. D., Miroshnichenko, Y. Y., Yusubov, M. S., Perederina, I. A., Chi, K. W., & Poleshchuk, O. K. (2004). Halogenating and nitrating activity of reagents based on sodium nitrate and alkali metal halides in acetic acid. Russian Journal of Organic Chemistry, 40(7), 917-923. https://doi.org/10.1023/B:RUJO.0000045178.33131.c2

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abstract = "Alkali metal halides NaF, KCl, and KBr sharply enhance the nitrating activity of sodium nitrate in acetic acid with respect to 9-methylcarbazole. In the presence of KI and KBr, both nitration and halogenation of the substrate occurs, while KCl and NaF promote only the nitration process. The results may be interpreted in terms of formation of the corresponding nitryl halides XNO2 (X = F, Cl, Br, I) whose structure and reactivity were examined in the framework of the density functional theory (DFT B3LYP/3-21G*).",

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AU - Filimonov, V. D.

AU - Miroshnichenko, Yulia Yurievna

AU - Yusubov, M. S.

AU - Perederina, I. A.

AU - Chi, Ki Whan

AU - Poleshchuk, O. Kh

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AB - Alkali metal halides NaF, KCl, and KBr sharply enhance the nitrating activity of sodium nitrate in acetic acid with respect to 9-methylcarbazole. In the presence of KI and KBr, both nitration and halogenation of the substrate occurs, while KCl and NaF promote only the nitration process. The results may be interpreted in terms of formation of the corresponding nitryl halides XNO2 (X = F, Cl, Br, I) whose structure and reactivity were examined in the framework of the density functional theory (DFT B3LYP/3-21G*).

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10.1023/B:RUJO.0000045178.33131.c2