Frija, L.Reva, I. D.Gómez-Zavaglia, A.Cristiano, Maria Lurdes SantosFausto, R.2014-06-072014-06-072007Frija, L. M. T.; Reva, I. D.; Gómez-Zavaglia, A.; Cristiano, M. L. S.; Fausto, R. UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone, Photochemical & Photobiological Sciences, 6, 11, 1170-1176, 2007.1474-905XAUT: MCR00716;http://hdl.handle.net/10400.1/4241The 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 (k > 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.engjournal article2014-06-05http://dx.doi.org/10.1039/b703961a