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SPECTROSCOPIC STUDIES OF ALCOHOLS: VI. INTRAMOLECULAR HYDROGEN BONDS IN ETHANOLAMINE AND ITS O- AND N-METHYL DERIVATIVES
Author(s) -
P. J. Krueger,
Howard D. Mettee
Publication year - 1965
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v65-411
Subject(s) - chemistry , intramolecular force , conformational isomerism , ethanolamine , hydrogen bond , enthalpy , crystallography , hydrogen , methyl group , computational chemistry , stereochemistry , group (periodic table) , molecule , organic chemistry , thermodynamics , physics
The competitive intramolecular [Formula: see text] hydrogen bonding in ethanolamine and N-methylethanolamine has been studied in dilute C 2 Cl 4 solution by means of the temperature dependence of the fundamental OH and NH stretching bands. Of the three conformers identified for each of these compounds, the least stable shows a distinct band which is assigned to a "terminal" OH group involved in an intramolecular [Formula: see text] hydrogen bond. Enthalpy differences between conformers are reported and discussed, and compared with those found for the conformational equilibria in 2-methoxyethylamine and N,N-dimethyl-ethanolamine.

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