European Journal of Organic Chemistry, volume 1996, issue 7, pages 1041-1053
Photochemical Fragmentation of Unsubstituted Tetrazole, 1,2,3-Triazole, and 1,2,4-Triazole: First Matrix-Spectroscopic Identification of Nitrilimine HCNNH
Publication type: Journal Article
Publication date: 2006-01-25
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.8
ISSN: 1434193X, 10990690
General Chemistry
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Equilibria between the tautomers of heterocyclic azoles like 1, 2, and 4 have been studied many times. We here show that the application of density functional methods in combination with matrix IR spectroscopy is a useful tool for determining which protomer is preferred in rare gas matrices and thus also can be assumed to dominate in the gas phase. Photolysis of tetrazole (4) in cryogenic matrices allows the IR-spectroscopic identification of a new CH2N2 isomer, the long soughtafter nitrilimine HCNNH (6). Flash pyrolysis of 4 also yielded nitrilimine. Upon irradiation this species is converted to a second, previously unknown “isomer”, an HCN/NH complex 13. Nitrilimine (6) can also be generated by photolyzing 1,2,3- (1) and 1,2,4-triazole (2) in Ar matrices. The complex photochemistry of all three heterocyclic precursor compounds was unveiled. Our findings were supported by isotopic substitution experiments and by high-level ab initio calculations. Moreover, the IR bands of iminocyanide HNCN were tentatively assigned. This radical has up to now not been observed in a matrix.
Top-30
Citations by journals
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1 publication, 4%
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1 publication, 4%
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1 publication, 4%
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1 publication, 4%
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1 publication, 4%
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1 publication, 4%
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Russian Chemical Reviews
1 publication, 4%
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Citations by publishers
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7
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American Chemical Society (ACS)
7 publications, 28%
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Wiley
4 publications, 16%
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Elsevier
4 publications, 16%
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2 publications, 8%
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Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 8%
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Springer Nature
1 publication, 4%
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Walter de Gruyter
1 publication, 4%
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American Institute of Physics (AIP)
1 publication, 4%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 4%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Maier G. et al. Photochemical Fragmentation of Unsubstituted Tetrazole, 1,2,3-Triazole, and 1,2,4-Triazole: First Matrix-Spectroscopic Identification of Nitrilimine HCNNH // European Journal of Organic Chemistry. 2006. Vol. 1996. No. 7. pp. 1041-1053.
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Maier G., Eckwert J., Bothur A., Reisenauer H. P., Schmidt C. Photochemical Fragmentation of Unsubstituted Tetrazole, 1,2,3-Triazole, and 1,2,4-Triazole: First Matrix-Spectroscopic Identification of Nitrilimine HCNNH // European Journal of Organic Chemistry. 2006. Vol. 1996. No. 7. pp. 1041-1053.
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TY - JOUR
DO - 10.1002/jlac.199619960704
UR - https://doi.org/10.1002/jlac.199619960704
TI - Photochemical Fragmentation of Unsubstituted Tetrazole, 1,2,3-Triazole, and 1,2,4-Triazole: First Matrix-Spectroscopic Identification of Nitrilimine HCNNH
T2 - European Journal of Organic Chemistry
AU - Maier, Günther
AU - Eckwert, Jürgen
AU - Bothur, Axel
AU - Reisenauer, Hans Peter
AU - Schmidt, Christiane
PY - 2006
DA - 2006/01/25 00:00:00
PB - Wiley
SP - 1041-1053
IS - 7
VL - 1996
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2006_Maier,
author = {Günther Maier and Jürgen Eckwert and Axel Bothur and Hans Peter Reisenauer and Christiane Schmidt},
title = {Photochemical Fragmentation of Unsubstituted Tetrazole, 1,2,3-Triazole, and 1,2,4-Triazole: First Matrix-Spectroscopic Identification of Nitrilimine HCNNH},
journal = {European Journal of Organic Chemistry},
year = {2006},
volume = {1996},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/jlac.199619960704},
number = {7},
pages = {1041--1053},
doi = {10.1002/jlac.199619960704}
}
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MLA
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Maier, Günther, et al. “Photochemical Fragmentation of Unsubstituted Tetrazole, 1,2,3-Triazole, and 1,2,4-Triazole: First Matrix-Spectroscopic Identification of Nitrilimine HCNNH.” European Journal of Organic Chemistry, vol. 1996, no. 7, Jan. 2006, pp. 1041-1053. https://doi.org/10.1002/jlac.199619960704.