GROUND-STATE AND EXCITED-STATE TAUTOMERISM IN 2-(3'-HYDROXY-2'-PYRIDYL)BENZIMIDAZOLE

被引：0
作者：
PRIETO, FR
RODRIGUEZ, MCR
GONZALEZ, MM
FERNANDEZ, MAR
机构：
来源：
JOURNAL OF PHYSICAL CHEMISTRY | 1994年 / 98卷 / 35期
关键词：
D O I：
暂无
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 tautomerism of 2-(3'-hydroxyl-2'-pyridyl)benzimidazole (HPyBI) in the ground and first excited singlet states was investigated by UV-vis absorption spectroscopy, by steady-state and time-resolved fluorescence spectroscopy, and by semiempirical (AM1) calculations (including exploration of the potential energy surface for the interconversion process and the effect of solvation). We conclude that ground-state HPyBI is enolic in nonaqueous solvents, whereas in water the keto and enol forms have almost the same energy and are present in equilibrium. In all the solvents considered, practically the only excited tautomer observed is the keto form, which is created from the enol form by ultrafast intramolecular proton transfer.
引用
收藏
页码：8666 / 8672
页数：7
相关论文
共 50 条
[1]   A PROTON-TRANSFER LASER [J].
ACUNA, AU ;
COSTELA, A ;
MUNOZ, JM .
JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (13) :2807-2808
[2]   TRIPLET-STATE FORMATION AND CIS-]TRANS ISOMERIZATION IN THE EXCITED SINGLET-STATE OF THE KETO TAUTOMER OF 2-(2'-HYDROXYPHENYL)BENZOTHIAZOLE [J].
ALSOUFI, W ;
GRELLMANN, KH ;
NICKEL, B .
CHEMICAL PHYSICS LETTERS, 1990, 174 (06) :609-616
[3]   KETO-ENOL TAUTOMERIZATION OF 2-(2'-HYDROXYPHENYL)BENZOXAZOLE AND 2-(2'-HYDROXY-4'-METHYLPHENYL)BENZOXAZOLE IN THE TRIPLET-STATE - HYDROGEN TUNNELING AND ISOTOPE EFFECTS .1. TRANSIENT ABSORPTION KINETICS [J].
ALSOUFI, W ;
GRELLMANN, KH ;
NICKEL, B .
JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (25) :10503-10509
[4]   SINGLET EXCITED-STATE INTRAMOLECULAR PROTON-TRANSFER IN 2-(2'-HYDROXYPHENYL)BENZOXAZOLE - SPECTROSCOPY AT LOW-TEMPERATURES, FEMTOSECOND TRANSIENT ABSORPTION, AND MNDO CALCULATIONS [J].
ARTHENENGELAND, T ;
BULTMANN, T ;
ERNSTING, NP ;
RODRIGUEZ, MA ;
THIEL, W .
CHEMICAL PHYSICS, 1992, 163 (01) :43-53
[5]   INTRAMOLECULAR PROTON-TRANSFER AND EXCITED-STATE RELAXATION IN 2-(2-HYDROXYPHENYL)BENZOTHIAZOLE [J].
BARBARA, PF ;
BRUS, LE ;
RENTZEPIS, PM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) :5631-5635
[6]   PICOSECOND KINETIC AND VIBRATIONALLY RESOLVED SPECTROSCOPIC STUDIES OF INTRAMOLECULAR EXCITED-STATE HYDROGEN-ATOM TRANSFER [J].
BARBARA, PF ;
WALSH, PK ;
BRUS, LE .
JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (01) :29-34
[7]   DISPLACEMENT OF PROTOMERIC EQUILIBRIA BY SELF-ASSOCIATION - HYDROXYPYRIDINE-PYRIDONE AND MERCAPTOPYRIDINE-THIOPYRIDONE ISOMER PAIRS [J].
BEAK, P ;
COVINGTON, JB ;
SMITH, SG ;
WHITE, JM ;
ZEIGLER, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (08) :1354-1362
[8]   A COMPREHENSIVE INVESTIGATION OF THE PHOTOPHYSICS AND PHOTOCHEMISTRY OF SALICYLIDENEANILINE AND DERIVATIVES OF PHENYLBENZOTHIAZOLE INCLUDING SOLVENT EFFECTS [J].
BECKER, RS ;
LENOBLE, C ;
ZEIN, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1987, 91 (13) :3509-3517
[9]   LACTIM-LACTAM TAUTOMERIC EQUILIBRIA OF 2-HYDROXYPYRIDINES .1. CATION BINDING, DIMERIZATION, AND INTERCONVERSION MECHANISM IN APROTIC-SOLVENTS - SPECTROSCOPIC AND TEMPERATURE-JUMP KINETIC STUDY [J].
BENSAUDE, O ;
CHEVRIER, M ;
DUBOIS, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (22) :7055-7060
[10]   INTRAMOLECULAR NONDISSOCIATIVE PROTON-TRANSFER IN AQUEOUS-SOLUTIONS OF TAUTOMERIC HETEROCYCLES - TEMPERATURE-JUMP KINETIC STUDY [J].
BENSAUDE, O ;
DREYFUS, M ;
DODIN, G ;
DUBOIS, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (13) :4438-4446
12345