High-resolution electronic spectra of 2-hydroxy and 2-aminopyridine. Perturbing effects of the nitrogen atom in the aromatic ring

被引:28
作者
Borst, DR [1 ]
Roscioli, JR [1 ]
Pratt, DW [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
D O I
10.1021/jp0140769
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
High resolution. rotationally resolved electronic spectra of 2-hydroxypyridine (2HP) and 2-aminopyridine (2AP, at similar to277 and similar to299 nm, respectively) have been observed and fit using rigid-rotor Hamiltonians to within lifetime-limited resolutions of 170 and 120 MHz. respectively. The derived values of the rotational constants are very similar to those of phenol and aniline. However, 2HP and 2AP each exhibit inertial axis tilting, large rotations of their SI-So electronic transition moments, and intramolecular hydrogen bonds, making them very different from their hydrocarbon analogues. Possible reasons for this behavior are discussed.
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页码:4022 / 4027
页数:6
相关论文
共 23 条
[1]   High resolution optothermal spectroscopy of pyridine in the S1 state [J].
Becucci, M ;
Lakin, NM ;
Pietraperzia, G ;
Salvi, PR ;
Castellucci, E ;
Kerstel, ERT .
JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (24) :10399-10405
[2]   High resolution UV spectroscopy of phenol and the hydrogen bonded phenol-water cluster [J].
Berden, G ;
Meerts, WL ;
Schmitt, M ;
Kleinermanns, K .
JOURNAL OF CHEMICAL PHYSICS, 1996, 104 (03) :972-982
[3]   NEW METHOD FOR BAND CONTOUR ANALYSIS WITH APPLICATION TO SPECTRUM OF PYRIDINE-4-D1 [J].
BIRSS, FW ;
COLSON, SD ;
RAMSAY, DA .
CANADIAN JOURNAL OF PHYSICS, 1973, 51 (10) :1031-1038
[4]   INTERPRETATION OF ROTATIONAL CONSTANTS OF FIRST SINGLET EXCITED STATE OF SUBSTITUTED BENZENES IN TERMS OF MOLECULAR GEOMETRY [J].
CVITAS, T ;
HOLLAS, JM ;
KIRBY, GH .
MOLECULAR PHYSICS, 1970, 19 (03) :305-&
[5]  
Eliel E.L., 1994, Stereochemistry of Organic Compounds
[6]  
Frisch M. J., 2016, Gaussian, V16
[7]   GAS-PHASE TAUTOMERIC EQUILIBRIUM OF 2-PYRIDINONE AND 2-HYDROXYPYRIDINE BY MICROWAVE SPECTROSCOPY [J].
HATHERLEY, LD ;
BROWN, RD ;
GODFREY, PD ;
PIERLOT, AP ;
CAMINATI, W ;
DAMIANI, D ;
MELANDRI, S ;
FAVERO, LB .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (01) :46-51
[8]   INTRAMOLECULAR HYDROGEN-BOND IN THE GROUND AND EXCITED ELECTRONIC STATES OF 2-HYDROXYQUINOLINE - A STUDY USING HIGH-RESOLUTION LASER SPECTROSCOPY [J].
HELD, A ;
PLUSQUELLIC, DF ;
TOMER, JL ;
PRATT, DW .
JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (07) :2877-2881
[9]   INERTIAL AXIS REORIENTATION IN THE S1[-S0 ELECTRONIC-TRANSITION OF 2-PYRIDONE - A ROTATIONAL DUSCHINSKY EFFECT - STRUCTURAL AND DYNAMIC CONSEQUENCES [J].
HELD, A ;
CHAMPAGNE, BB ;
PRATT, DW .
JOURNAL OF CHEMICAL PHYSICS, 1991, 95 (12) :8732-8743
[10]   ELECTRONIC ASSIGNMENT AS 1A'(PIPI!)-1A' OF 2980 A SYSTEM OF 2-AMINOPYRIDINE BY ROTATIONAL BAND CONTOUR ANALYSIS [J].
HOLLAS, JM ;
KIRBY, GH ;
WRIGHT, RA .
MOLECULAR PHYSICS, 1970, 18 (03) :327-&