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

Yulia Yurievna Kulmanakova, M. S. Yusubov, I. A. Perederina, Ki Whan Chi

Research output: Chapter in Book/Report/Conference proceedingConference contribution

1 Citation (Scopus)

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 languageEnglish
Title of host publicationProceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology
PublisherInstitute of Electrical and Electronics Engineers Inc.
Pages222-226
Number of pages5
Volume1
ISBN (Print)0780364864, 9780780364868
DOIs
Publication statusPublished - 2000
Event4th Korea-Russia International Symposium on Science and Technology, KORUS 2000 - Ulsan, Korea, Republic of
Duration: 27 Jun 20001 Jul 2000

Other

Other4th Korea-Russia International Symposium on Science and Technology, KORUS 2000
CountryKorea, Republic of
CityUlsan
Period27.6.001.7.00

Fingerprint

Unsaturated compounds
Halogenation
Alkali Metals
Nitration
Aromatic compounds
Alkali metals
Nitrates
Free radicals
Free Radicals
Temperature
Thermodynamic properties
Rupture
N-methylcarbazole
potassium bromide

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

Cite this

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 proceedingConference 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
Kulmanakova, Yulia Yurievna ; Yusubov, M. S. ; Perederina, I. A. ; Chi, Ki Whan. / Halogenation and nitration of aromatics and unsaturated compounds by halides and nitrates of alkali metals. Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology. Vol. 1 Institute of Electrical and Electronics Engineers Inc., 2000. pp. 222-226
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AU - Kulmanakova, Yulia Yurievna

AU - Yusubov, M. S.

AU - Perederina, I. A.

AU - Chi, Ki Whan

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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).

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