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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.
weak hydrogen bond
medium hydrogen bond
hydrogen bonding chain
trifluoromethylated amino alcohols
structure of hydrogen bond
Digital Object Identifer:10.1016/j.jfluchem.2005.04.014
Published with permission from the copyright holder. This is the institute's copy, as published in the Journal of Fluorine Chemistry, August 2005, Volume 126, Issue 8, Pages 1134-1139.
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Copyright © 2005 Elsevier B.V. All rights reserved.
Journal of Fluorine Chemistry
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