Photochemistry of 2-(3-benzoylphenyl)propionic acid (ketoprofen) .1. A picosecond and nanosecond time resolved study in aqueous solution

被引:110
作者
Monti, S [1 ]
Sortino, S [1 ]
DeGuidi, G [1 ]
Marconi, G [1 ]
机构
[1] UNIV CATANIA, DIPARTIMENTO SCI CHIM, I-95125 CATANIA, ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS | 1997年 / 93卷 / 13期
关键词
D O I
10.1039/a700367f
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The photochemistry of ketoprofen (KPF), 2-(3-benzoylphenyl)propionic acid, has been studied in aqueous solutions by time resolved (picosecond and nanosecond) spectroscopic techniques. Excited-state calculations were performed. The overall reactivity of the molecule was rationalized within a scheme in which the lowest triplet state can undergo intramolecular electron transfer and photoionization. The main pathway for the;formation of the decarboxylated photoproducts was shown to involve intramolecular electron transfer and to pass through triplet biradicals.
引用
收藏
页码:2269 / 2275
页数:7
相关论文
共 29 条
[1]   MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].
ALLINGER, NL ;
YUH, YH ;
LII, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566
[2]  
ALLINGER NL, 1989, QCPE B, V9, P2
[3]   A LASER FLASH-PHOTOLYSIS STUDY OF PARAQUAT REDUCTION BY PHOTOGENERATED AROMATIC KETYL RADICALS AND CARBONYL TRIPLETS [J].
BARALTOSH, S ;
CHATTOPADHYAY, SK ;
DAS, PK .
JOURNAL OF PHYSICAL CHEMISTRY, 1984, 88 (07) :1404-1408
[4]   PHYSICAL QUENCHING AND CHEMICAL-REACTION OF SINGLET MOLECULAR-OXYGEN WITH AZO DYES [J].
BORTOLUS, P ;
MONTI, S ;
ALBINI, A ;
FASANI, E ;
PIETRA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :534-540
[5]   Photocyclisation of 2-pyridyl phenyl ketone - A reaction driven by hydrogen bonding [J].
Bortolus, P ;
Elisei, F ;
Favaro, G ;
Monti, S ;
Ortica, F .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1996, 92 (11) :1841-1851
[6]   PHOTOCHEMICAL AND PHOTOBIOLOGICAL PROPERTIES OF KETOPROFEN ASSOCIATED WITH THE BENZOPHENONE CHROMOPHORE [J].
BOSCA, F ;
MIRANDA, MA ;
CARGANICO, G ;
MAULEON, D .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1994, 60 (02) :96-101
[7]   PHOTODECARBOXYLATION - MECHANISM AND SYNTHETIC UTILITY [J].
BUDAC, D ;
WAN, P .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1992, 67 (02) :135-166
[8]   CRITICAL-REVIEW OF RATE CONSTANTS FOR REACTIONS OF HYDRATED ELECTRONS, HYDROGEN-ATOMS AND HYDROXYL RADICALS (.OH/.O-) IN AQUEOUS-SOLUTION [J].
BUXTON, GV ;
GREENSTOCK, CL ;
HELMAN, WP ;
ROSS, AB .
JOURNAL OF PHYSICAL AND CHEMICAL REFERENCE DATA, 1988, 17 (02) :513-886
[9]   PHOTOSENSITIZING ACTION OF NONSTEROIDAL ANTIINFLAMMATORY DRUGS ON CELL-MEMBRANES AND DESIGN OF PROTECTIVE SYSTEMS [J].
CONDORELLI, G ;
DEGUIDI, G ;
GIUFFRIDA, S ;
COSTANZO, LL .
COORDINATION CHEMISTRY REVIEWS, 1993, 125 (1-2) :115-127
[10]   MOLECULAR MECHANISM OF DRUG PHOTOSENSITIZATION .2. PHOTOHEMOLYSIS SENSITIZED BY KETOPROFEN [J].
COSTANZO, LL ;
DEGUIDI, G ;
CONDORELLI, G ;
CAMBRIA, A ;
FAMA, M .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1989, 50 (03) :359-365