Discrimination of rotamers of aryl alcohol homologues by infrared-ultraviolet double-resonance spectroscopy in a supersonic jet

被引:68
作者
Guchhait, N [1 ]
Ebata, T [1 ]
Mikami, N [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/ja9829618
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Infrared-ultraviolet double-resonance spectroscopy has been applied to discriminate rotamers of jet-cooled aryl alcohol homologues, phi-(CH2)(n)OH, where phi represents phenyl group and n = 1, 2, and 3 correspond to benzyl, phenethyl, and 3-phenylpropyl alcohols, respectively. Experimental results indicate that different OH stretching frequencies are associated with different rotamers and that the ability of intramolecular hydrogen bonding with the benzene pi-electron decreases with an increase in alkyl chain length. In each aryl alcohol, the most prominent species in jets corresponds to the non-hydrogen-bonded rotamer having higher OH stretching frequency.
引用
收藏
页码:5705 / 5711
页数:7
相关论文
共 41 条
[1]   ROTATIONAL-ISOMERISM .22. NMR-STUDY OF OH .. PI-BONDING AND CONFORMATIONS OF BENZYL ALCOHOL AND DERIVATIVES [J].
ABRAHAM, RJ ;
BAKKE, JM .
TETRAHEDRON, 1978, 34 (19) :2947-2951
[2]   Combined high resolution infrared and microwave study of bromochlorofluoromethane [J].
Bauder, A ;
Bell, A ;
Luckhaus, D ;
Muller, F ;
Quack, M .
JOURNAL OF CHEMICAL PHYSICS, 1997, 106 (18) :7558-7570
[3]   MOST STABLE CONFORMER OF 2-PHENYLPROPANAL ELUCIDATED BY SUPERSONIC JET SPECTROSCOPY [J].
CHOUNAN, Y ;
EBATA, T ;
YAMAMOTO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :3167-3170
[4]   Conformational choice, hydrogen bonding, and rotation of the S1←S0 electronic transition moment in 2-phenylethyl alcohol, 2-phenylethylamine, and their water clusters [J].
Dickinson, JA ;
Hockridge, MR ;
Kroemer, RT ;
Robertson, EG ;
Simons, JP ;
McCombie, J ;
Walker, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2622-2632
[5]   OH stretching vibrations of phenol-(H2O)(1) and phenol-(H2O)(3) in the S-1 state [J].
Ebata, T ;
Mizuochi, N ;
Watanabe, T ;
Mikami, N .
JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (02) :546-550
[6]  
Ebata T, 1998, NONLINEAR SPECTROSCOPY FOR MOLECULAR STRUCTURE DETERMINATION, P149
[7]   EVIDENCE FOR THE CYCLIC FORM OF PHENOL TRIMER - VIBRATIONAL SPECTROSCOPY OF THE OH STRETCHING VIBRATIONS OF JET-COOLED PHENOL DIMER AND TRIMER [J].
EBATA, T ;
WATANABE, T ;
MIKAMI, N .
JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (16) :5761-5764
[8]   Photoelectron spectroscopy of liquid water, some alcohols, and pure nonane in free micro jets [J].
Faubel, M ;
Steiner, B ;
Toennies, JP .
JOURNAL OF CHEMICAL PHYSICS, 1997, 106 (22) :9013-9031
[9]   NONLINEAR RAMAN STUDIES OF WEAKLY-BOUND COMPLEXES AND CLUSTERS IN MOLECULAR-BEAMS [J].
FELKER, PM ;
MAXTON, PM ;
SCHAEFFER, MW .
CHEMICAL REVIEWS, 1994, 94 (07) :1787-1805
[10]   Infra-red absorption of the hydroxyl group in relation to inter- and intramolecular hydrogen bonds. [J].
Fox, JJ ;
Martin, AE .
TRANSACTIONS OF THE FARADAY SOCIETY, 1940, 36 :0897-0911