Matrix-isolation and computational study of salicylhydroxamic acid and its photochemical degradation.
The IR absorption spectrum of salicylhydroxamic acid (sha) isolated in an argon matrix at 12-21 K has been recorded. Calculations of all the possible entgegen and zusammen keto conformers of sha have been performed at the B3LYP/6-311++G(d,p) level of theory. The computed energies, optimized structures, and relative abundances show that sha exists in the matrix as the z,z,z,z-conformer [relative to the C-O(-H), C-C(-N), C-N and N-O bonds, respectively] and is stabilized by two intramolecular H-bonds. Photofragmentation of the compound in matrix and methanol-water solution has been obtained by irradiation with visible and ultraviolet light. o-Hydroxyphenylisocyanate is the main photolysis product in an argon matrix, while salicylamide is the primary photolysis product in methanol-water solution.
Kaczor
Agnieszka
A
Faculty of Chemistry, Jagiellonian University, ul. Ingardena 3, 30-060 Krakow, Poland.
Szczepanski
Jan
J
Vala
Martin
M
Proniewicz
Leonard M
LM
D002244:Carbon / Q000737:chemistry; D002627:Chemistry, Physical / Q000379:methods; D003198:Computer Simulation; D006859:Hydrogen / Q000737:chemistry; D006860:Hydrogen Bonding; D000432:Methanol / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry; D010777:Photochemistry / Q000379:methods*; D012457:Salicylamides / Q000737:chemistry*; D012984:Software; D013055:Spectrophotometry, Infrared / Q000379:methods; D013696:Temperature; D014867:Water / Q000737:chemistry
D012457:Salicylamides; D014867:Water; D002244:Carbon; D006859:Hydrogen; C005703:salicylhydroxamic acid; D010100:Oxygen; D000432:Methanol