info:eu-repo/semantics/article
UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone
Fecha
2007-12Registro en:
Frija, L. M. T.; Reva, I. D.; Gomez Zavaglia, Andrea; Cristiano, M. L. S.; Fausto, R.; UV-induced photochemistry of matrix-isolated 1-phenyl-4-allyl-tetrazolone; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 6; 11; 12-2007; 1170-1176
1474-905X
CONICET Digital
CONICET
Autor
Frija, L. M. T.
Reva, I. D.
Gomez Zavaglia, Andrea
Cristiano, M. L. S.
Fausto, R.
Resumen
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 (lambda > 235 nm) of matrix-isolated PAT induces three types of photofragmentation: (1) production of phenylazide and allyl-isocyanate, with phenylazide then losing N(2) to yield 1-aza-1,2,4,6-cycloheptatetraene; (2) formation of phenyl-isocyanate and allylazide; (3) N(2) 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.