Please use this identifier to cite or link to this item: http://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: http://hdl.handle.net/10316/17938
DOI: 10.1039/B703961A
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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