Intermolecular-medium and intramolecular-weak hydrogen bonding chains in the crystals of chiral trifluoromethylated amino alcohols

被引:16
作者
Katagiri, T [1 ]
Fujiwara, Y [1 ]
Takahashi, S [1 ]
Uneyama, K [1 ]
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
基金
日本科学技术振兴机构;
关键词
hydrogen bond; weak hydrogen bond; medium hydrogen bond; hydrogen bonding chain; trifluoromethylated amino alcohols; chiral recognition; structure of hydrogen bond;
D O I
10.1016/j.jfluchem.2005.04.014
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学]; 081704 [应用化学];
摘要
A structural feature of hydrogen bonding chains found in the crystals of trifluoromethylated amino alcohols is reported. Hydrogen bondings of 3-(N,N-dialkylamino)-1,1,1-trifluoro-2-propanols construct chiral spiral hydrogen bonding chains. Lone pairs on the nitrogen atoms of the amino alcohols participate in two hydrogen bondings. Detailed structural analysis of the hydrogen bonds of the 3-(N,N-dimethylamino)-1,1,1-trifluoro-2-propanol suggested that the chain built up with alternating intermolecular-medium and intramolecular-weak hydrogen bonds. The medium intermolecular hydrogen bond, which transfers a proton from the hydroxy group to the amino nitrogen, would make a tentative zwitterionic form of the molecule. Then, electrostatic attraction between the charges in the zwitterion centers induced a weak intramolecular hydrogen bond. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:1134 / 1139
页数:6
相关论文
共 26 条
[1]
Fluorinated alcohols:: A new medium for selective and clean reaction [J].
Bégué, JP ;
Bonnet-Delpon, D ;
Crousse, B .
SYNLETT, 2004, (01) :18-29
[2]
Desiraju G. R., 1999, WEAK HYDROGEN BOND S, P13
[3]
MOLECULAR RECOGNITION AMONG ALCOHOLS AND AMINES - SUPER-TETRAHEDRAL CRYSTAL ARCHITECTURES OF LINEAR DIPHENOL-DIAMINE COMPLEXES AND AMINOPHENOLSE [J].
ERMER, O ;
ELING, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (05) :925-944
[4]
Trifluoromethylated amino alcohols as chiral ligands for highly enantioselective Reformatsky reaction [J].
Fujiwara, Y ;
Katagiri, T ;
Uneyama, K .
TETRAHEDRON LETTERS, 2003, 44 (32) :6161-6163
[5]
FURUHASHI K, 1992, CHIRALITY IND
[6]
MOLECULAR RECOGNITION AND SELF-ASSEMBLY BY NON-AMIDIC HYDROGEN-BONDING - AN EXCEPTIONAL ASSEMBLER OF NEUTRAL AND CHARGED SUPRAMOLECULAR STRUCTURES [J].
HANESSIAN, S ;
SIMARD, M ;
ROELENS, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (29) :7630-7645
[7]
KINETIC RESOLUTION OF RACEMIC ALDEHYDES BY ENANTIOSELECTIVE ALKYLATION [J].
HAYASHI, M ;
MIWATA, H ;
OGUNI, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05) :1167-1171
[8]
AN EFFICIENT PREPARATION OF OPTICALLY-ACTIVE ALLYLIC ALCOHOLS, 2-FURYL ALCOHOLS AND 2-THIENYL ALCOHOLS BY CATALYTIC ASYMMETRIC ALKYLATION [J].
HAYASHI, M ;
KANEKO, T ;
OGUNI, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :25-28
[9]
Practical asymmetric synthetic route to 4,4,4-trifluoro-3-hydroxybutyrate: Head-to-tail and head-to-head crystallizations through double and single hydrogen bonds of hetero- and homochiral 4,4,4-trifluoro-3-hydroxybutyrophenones [J].
Ishii, A ;
Kanai, M ;
Higashiyama, K ;
Mikami, K .
CHIRALITY, 2002, 14 (09) :709-712
[10]
Jacques J., 1981, Enantiomers, Racemates and Resolutions