Journal of Organic Chemistry, volume 81, issue 23, pages 11656-11663
Photochemistry of 1- and 2-Methyl-5-aminotetrazoles: Structural Effects on Reaction Pathways
1
CCMAR
and Department of Chemistry and Pharmacy, F.C.T., University of Algarve, P-8005-039 Faro, Portugal
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Publication type: Journal Article
Publication date: 2016-11-17
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
The influence of the position of the methyl substituent in 1- and 2-methyl-substituted 5-aminotetrazoles on the photochemistry of these molecules is evaluated. The two compounds were isolated in an argon matrix (15 K) and the matrix was subjected to in situ narrowband UV excitation at different wavelengths, which induce selectively photochemical transformations of different species (reactants and initially formed photoproducts). The progress of the reactions was followed by infrared spectroscopy, supported by quantum chemical calculations. It is shown that the photochemistries of the two isomers, 1-methyl-(1H)-tetrazole-5-amine (1a) and 2-methyl-(2H)-tetrazole-5-amine (1b), although resulting in a common intermediate diazirine 3, which undergoes subsequent photoconversion into 1-amino-3-methylcarbodiimide (H2N-N═C═N-CH3), show marked differences: formation of the amino cyanamide 4 (H2N-N(CH3)-C≡N) is only observed from the photocleavage of the isomer 1a, whereas formation of the nitrile imine 2 (H2N-C-═N+═N-CH3) is only obtained from photolysis of 1b. The exclusive formation of nitrile imine from the isomer 1b points to the possibility that only the 2H-tetrazoles forms can give a direct access to nitrile imines, while observation of the amino cyanamide 4 represents a novel reaction pathway in the photochemistry of tetrazoles and seems to be characteristic of 1H-tetrazoles. The structural and vibrational characterization of both reactants and photoproducts has been undertaken.
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Ismael A. et al. Photochemistry of 1- and 2-Methyl-5-aminotetrazoles: Structural Effects on Reaction Pathways // Journal of Organic Chemistry. 2016. Vol. 81. No. 23. pp. 11656-11663.
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Ismael A., Fausto R., Cristiano M. L. S. Photochemistry of 1- and 2-Methyl-5-aminotetrazoles: Structural Effects on Reaction Pathways // Journal of Organic Chemistry. 2016. Vol. 81. No. 23. pp. 11656-11663.
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TY - JOUR
DO - 10.1021/acs.joc.6b02023
UR - https://doi.org/10.1021/acs.joc.6b02023
TI - Photochemistry of 1- and 2-Methyl-5-aminotetrazoles: Structural Effects on Reaction Pathways
T2 - Journal of Organic Chemistry
AU - Ismael, A
AU - Fausto, Rui
AU - Cristiano, Maria L. S.
PY - 2016
DA - 2016/11/17 00:00:00
PB - American Chemical Society (ACS)
SP - 11656-11663
IS - 23
VL - 81
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2016_Ismael,
author = {A Ismael and Rui Fausto and Maria L. S. Cristiano},
title = {Photochemistry of 1- and 2-Methyl-5-aminotetrazoles: Structural Effects on Reaction Pathways},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.joc.6b02023},
number = {23},
pages = {11656--11663},
doi = {10.1021/acs.joc.6b02023}
}
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Ismael, A., et al. “Photochemistry of 1- and 2-Methyl-5-aminotetrazoles: Structural Effects on Reaction Pathways.” Journal of Organic Chemistry, vol. 81, no. 23, Nov. 2016, pp. 11656-11663. https://doi.org/10.1021/acs.joc.6b02023.