Pure and Applied Chemistry, volume 92, issue 1, pages 49-62
Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability
1
CCMAR and Department of Chemistry and Pharmacy, F.C.T. , University of Algarve , P-8005-039 Faro , Portugal
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5
Departamento de Química e Farmácia, Faculdade de Ciências e Tecnologia , Campus de Gambelas, Universidade do Algarve , P-8005-039 Faro , Portugal
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6
CCMAR, F.C.T. , University of Algarve , P-8005-039 Faro , Portugal
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Publication type: Journal Article
Publication date: 2019-06-12
Journal:
Pure and Applied Chemistry
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor: 1.8
ISSN: 00334545, 13653075
General Chemistry
General Chemical Engineering
Abstract
The properties and applications of 2-methyl-(2H)-tetrazole-5-amino-saccharinate (2MTS) in catalysis and chelant-based chemotherapy stimulated investigations on its photostability. The photochemistry of monomeric 2MTS in solid argon (15 K) was compared with those of 2-methyl-(2H)-tetrazole-5-amine (2MT) and 1-methyl-(2H)-tetrazole-5-amine (1MT). Compounds were subjected to in situ narrowband UV-irradiation at different wavelengths. Reactions were followed by infrared spectroscopy, supported by B3LYP/6-311++G(d,p) calculations. Photochemical pathways for 2MT and 2MTS proved similar but photodegradation of 2MTS was 20× slower, unraveling the photostabilizing effect of the saccharyl moiety that extends into the nitrilimine formed from 2MTS and its antiaromatic 1H-diazirene isomer, which proved photostable at 290 nm, unlike the 1H-diazirene formed from 2MT. Analysis of the photochemistries of 2MTS/2MT (250 nm) and 1MT (222 nm), including energy trends calculated for the isomeric C2H5N3 species postulated/observed from photolysis and EPR results, enabled a deeper insight into the photodegradation mechanisms of 1,5-substituted and 2,5-substituted tetrazoles. We postulate a pivotal singlet state imidoylnitrene species, sN1, as common intermediate, which undergoes a Wolff-type isomerization to a stable carbodiimide. Photo-extrusion of N2 from 1,5-substituted tetrazoles generates sN1 directly but from 2,5-substituted tetrazoles it originates a nitrilimine, then a diazirene, which finally leads to sN1. Selective formation of cyanamide from 1MT requires photoisomerization between sN1 and sN2, accessible at 222 nm. EPR studies enabled the detection of methyl nitrene, arising from photolysis of 1H-diazirene intermediate.
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Ismael A. et al. Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability // Pure and Applied Chemistry. 2019. Vol. 92. No. 1. pp. 49-62.
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Ismael A., Abe M., Fausto R., Cristiano M. L. S. Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability // Pure and Applied Chemistry. 2019. Vol. 92. No. 1. pp. 49-62.
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TY - JOUR
DO - 10.1515/pac-2019-0402
UR - https://doi.org/10.1515/pac-2019-0402
TI - Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability
T2 - Pure and Applied Chemistry
AU - Ismael, Amin
AU - Abe, Manabu
AU - Fausto, Rui
AU - Cristiano, Maria L S
PY - 2019
DA - 2019/06/12 00:00:00
PB - Walter de Gruyter
SP - 49-62
IS - 1
VL - 92
SN - 0033-4545
SN - 1365-3075
ER -
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@article{2019_Ismael,
author = {Amin Ismael and Manabu Abe and Rui Fausto and Maria L S Cristiano},
title = {Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability},
journal = {Pure and Applied Chemistry},
year = {2019},
volume = {92},
publisher = {Walter de Gruyter},
month = {jun},
url = {https://doi.org/10.1515/pac-2019-0402},
number = {1},
pages = {49--62},
doi = {10.1515/pac-2019-0402}
}
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Ismael, Amin, et al. “Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability.” Pure and Applied Chemistry, vol. 92, no. 1, Jun. 2019, pp. 49-62. https://doi.org/10.1515/pac-2019-0402.