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 proceeding › Conference 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 2000 → 1 Jul 2000

Other

Other4th Korea-Russia International Symposium on Science and Technology, KORUS 2000
CountryKorea, Republic of
CityUlsan
Period27.6.00 → 1.7.00

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 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
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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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}",
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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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