Halogenation and nitration of aromatics and unsaturated compounds by halides and nitrates of alkali metals

Abstract

We have discovered that KI/NaNO₃ and KBr/NaNO₃ in AcOH possesse halogenation and nitration properties towards to 9-methylcarbazole in depending on temperature. So KBr/NaNO₃ has bromination activity at r.t. but it is nitration agent at 80°C. On the other hand KI/NaNO₃ provides the mixture of iod- and nitrocarbazoles at 80°C, and arising temperature up 80°C gives only 3-nitro- and 3,6-dinitro-9-methylcarbazoles. We suppose that weak iodination ability of KI/NaNO₃ is due to the fact that the intermediate nitriliodide I-NO₂ does not produce I⁺ but has a tendency to free-radical rupture. It was confirmed by ab initio quantum-chemical computations of nitrilhalogenides X-NO₂ (X=F,Cl,Br,I).

Original language	English
Title of host publication	Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology
Publisher	Institute of Electrical and Electronics Engineers Inc.
Pages	222-226
Number of pages	5
Volume	1
ISBN (Print)	0780364864, 9780780364868
DOIs	https://doi.org/10.1109/KORUS.2000.865956
Publication status	Published - 2000
Event	4th Korea-Russia International Symposium on Science and Technology, KORUS 2000 - Ulsan, Korea, Republic of Duration: 27 Jun 2000 → 1 Jul 2000

Other

Other	4th Korea-Russia International Symposium on Science and Technology, KORUS 2000
Country	Korea, Republic of
City	Ulsan
Period	27.6.00 → 1.7.00

Keywords

carbazole
halogenation
nitration

ASJC Scopus subject areas

Clinical Biochemistry
Computer Networks and Communications
Biotechnology
Civil and Structural Engineering
Mechanics of Materials
Electronic, Optical and Magnetic Materials
Materials Chemistry
Surfaces, Coatings and Films

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10.1109/KORUS.2000.865956

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Kulmanakova, Y. Y., Yusubov, M. S., Perederina, I. A., & Chi, K. W. (2000). Halogenation and nitration of aromatics and unsaturated compounds by halides and nitrates of alkali metals. In Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology (Vol. 1, pp. 222-226). [865956] Institute of Electrical and Electronics Engineers Inc.. https://doi.org/10.1109/KORUS.2000.865956

Halogenation and nitration of aromatics and unsaturated compounds by halides and nitrates of alkali metals. / Kulmanakova, Yulia Yurievna ; Yusubov, M. S.; Perederina, I. A.; Chi, Ki Whan.

Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology. Vol. 1 Institute of Electrical and Electronics Engineers Inc., 2000. p. 222-226 865956.

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

Kulmanakova, YY , Yusubov, MS, Perederina, IA & Chi, KW 2000, Halogenation and nitration of aromatics and unsaturated compounds by halides and nitrates of alkali metals. in Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology. vol. 1, 865956, Institute of Electrical and Electronics Engineers Inc., pp. 222-226, 4th Korea-Russia International Symposium on Science and Technology, KORUS 2000, Ulsan, Korea, Republic of, 27.6.00. https://doi.org/10.1109/KORUS.2000.865956

Kulmanakova YY , Yusubov MS, Perederina IA, Chi KW. Halogenation and nitration of aromatics and unsaturated compounds by halides and nitrates of alkali metals. In Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology. Vol. 1. Institute of Electrical and Electronics Engineers Inc. 2000. p. 222-226. 865956 https://doi.org/10.1109/KORUS.2000.865956

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title = "Halogenation and nitration of aromatics and unsaturated compounds by halides and nitrates of alkali metals",

abstract = "We have discovered that KI/NaNO3 and KBr/NaNO3 in AcOH possesse halogenation and nitration properties towards to 9-methylcarbazole in depending on temperature. So KBr/NaNO3 has bromination activity at r.t. but it is nitration agent at 80°C. On the other hand KI/NaNO3 provides the mixture of iod- and nitrocarbazoles at 80°C, and arising temperature up 80°C gives only 3-nitro- and 3,6-dinitro-9-methylcarbazoles. We suppose that weak iodination ability of KI/NaNO3 is due to the fact that the intermediate nitriliodide I-NO2 does not produce I+ but has a tendency to free-radical rupture. It was confirmed by ab initio quantum-chemical computations of nitrilhalogenides X-NO2 (X=F,Cl,Br,I).",

keywords = "carbazole, halogenation, nitration",

author = "Kulmanakova, {Yulia Yurievna} and Yusubov, {M. S.} and Perederina, {I. A.} and Chi, {Ki Whan}",

year = "2000",

doi = "10.1109/KORUS.2000.865956",

language = "English",

isbn = "0780364864",

volume = "1",

pages = "222--226",

booktitle = "Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology",

publisher = "Institute of Electrical and Electronics Engineers Inc.",

note = "4th Korea-Russia International Symposium on Science and Technology, KORUS 2000 ; Conference date: 27-06-2000 Through 01-07-2000",

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TY - GEN

T1 - Halogenation and nitration of aromatics and unsaturated compounds by halides and nitrates of alkali metals

AU - Kulmanakova, Yulia Yurievna

AU - Yusubov, M. S.

AU - Perederina, I. A.

AU - Chi, Ki Whan

PY - 2000

Y1 - 2000

N2 - We have discovered that KI/NaNO3 and KBr/NaNO3 in AcOH possesse halogenation and nitration properties towards to 9-methylcarbazole in depending on temperature. So KBr/NaNO3 has bromination activity at r.t. but it is nitration agent at 80°C. On the other hand KI/NaNO3 provides the mixture of iod- and nitrocarbazoles at 80°C, and arising temperature up 80°C gives only 3-nitro- and 3,6-dinitro-9-methylcarbazoles. We suppose that weak iodination ability of KI/NaNO3 is due to the fact that the intermediate nitriliodide I-NO2 does not produce I+ but has a tendency to free-radical rupture. It was confirmed by ab initio quantum-chemical computations of nitrilhalogenides X-NO2 (X=F,Cl,Br,I).

AB - We have discovered that KI/NaNO3 and KBr/NaNO3 in AcOH possesse halogenation and nitration properties towards to 9-methylcarbazole in depending on temperature. So KBr/NaNO3 has bromination activity at r.t. but it is nitration agent at 80°C. On the other hand KI/NaNO3 provides the mixture of iod- and nitrocarbazoles at 80°C, and arising temperature up 80°C gives only 3-nitro- and 3,6-dinitro-9-methylcarbazoles. We suppose that weak iodination ability of KI/NaNO3 is due to the fact that the intermediate nitriliodide I-NO2 does not produce I+ but has a tendency to free-radical rupture. It was confirmed by ab initio quantum-chemical computations of nitrilhalogenides X-NO2 (X=F,Cl,Br,I).

KW - carbazole

KW - halogenation

KW - nitration

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BT - Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology

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