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Molecular structure, vibrational spectra and photochemistry of 5-mercapto-1-methyltetrazole
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Abstract(s)
In this work, 5-mercapto-1-methyltetrazole was studied by low temperature matrix-isolation and solid-state infrared spectroscopy, DFT(B3LYP)/6-311CCG(d,p) calculations and photochemical methods. In the low temperature neat solid phase and isolated in an argon matrix, the compound was found to exist in the 1-methyl-1,4-dihydro-5H-tetrazole-5-thione tautomeric form. The infrared spectra of the compound were fully assigned and correlated with structural properties. In situ UV-irradiation (lO235 nm) of the matrix-isolated monomer is shown to induce
different photochemical processes, all of them involving cleavage of the tetrazole ring: e.g. (1) molecular nitrogen expulsion, with production of 1-methyl-1H-diazirene-3-thiol, which is produced in two different conformers; (2) ring cleavage leading to production of methyl isothiocyanate and azide; (3) simultaneous elimination of nitrogen and sulphur with production of N-methylcarbodiimide. Following these photoprocesses, subsequent reactions occur, leading to production of methyl diazene, carbon monosulphide and nitrogen hydride. Spectroscopic evidence of the production of the above-mentioned chemical species is provided.
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Keywords
5-Mercapto-1-methyltetrazole Matrix-isolation infrared spectroscopy Photochemistry N-methylcarbodiimide 1-Methyl-1H-diazirene-3-thiol Methyl isothiocyanate Azide Methyl diazene Carbon monosulphide Nitrogen hydride
Citation
Gómez-Zavaglia, A.; Reva, I.D.; Frija, L.; Cristiano, M.L.; Fausto, R. Molecular structure, vibrational spectra and photochemistry of 5-mercapto-1-methyltetrazole, Journal of Molecular Structure, 786, 2-3, 182-192, 2006.
