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https://hdl.handle.net/10316/17938
Title: | UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone | Authors: | Frija, L. M. T. Reva, I. D. Gómez-Zavaglia, A. Cristiano, M. L. S. Fausto, R. |
Issue Date: | Jul-2007 | Publisher: | The Royal Society of Chemistry | Serial title, monograph or event: | Photochemical & Photobiological Sciences | Volume: | 6 | Abstract: | The photochemistry and molecular structure of 1-phenyl-4-allyl-tetrazolone (PAT) was studied by FT-IR matrix isolation spectroscopy and DFT(B3LYP)/6-311++G(d,p) calculations. The spectrum of matrix-isolated PAT monomers agrees well with the sum spectrum of three conformers predicted theoretically. UV irradiation (λ > 235 nm) of matrix-isolated PAT induces three types of photofragmentation: (1) production of phenylazide and allyl-isocyanate, with phenylazide then losing N2 to yield 1-aza-1,2,4,6-cycloheptatetraene; (2) formation of phenyl-isocyanate and allylazide; (3) N2 elimination leading to formation of 1-allyl-2-phenyldiaziridin-3-one; this compound partially reacts further to form 1-allyl-1H-benzoimidazol-2(3H)-one. The observed photochemistry of the matrix-isolated PAT is distinct from the preferred photochemical fragmentation in solution, where 3,4-dihydro-3-phenylpyrimidin-2(1H)-one is produced as the primary photoproduct. | URI: | https://hdl.handle.net/10316/17938 | DOI: | 10.1039/B703961A | Rights: | openAccess |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais |
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File | Description | Size | Format | |
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Photochem. Photobiol. Sci., 6 (2007) 1170.pdf | 226.56 kB | Adobe PDF | View/Open |
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