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 | |
| 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 |
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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
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
}
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
UR - http://www.scopus.com/inward/record.url?scp=33745761102&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33745761102&partnerID=8YFLogxK
U2 - 10.1109/KORUS.2000.865956
DO - 10.1109/KORUS.2000.865956
M3 - Conference contribution
AN - SCOPUS:33745761102
SN - 0780364864
SN - 9780780364868
VL - 1
SP - 222
EP - 226
BT - Proceedings - KORUS 2000: 4th Korea-Russia International Symposium on Science and Technology
PB - Institute of Electrical and Electronics Engineers Inc.
ER -