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Intramolecular effects on the fundamental hydroxyl stretching vibration in derivatives of fats and related compounds
Author(s) -
Eddy C. Roland,
Showell John S.,
Zell Tatiana E.
Publication year - 1963
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02640697
Subject(s) - intramolecular force , chemistry , intermolecular force , hydrogen bond , photochemistry , carbon tetrachloride , hydroxyl radical , infrared , hydrogen , radical , medicinal chemistry , organic chemistry , molecule , physics , optics
The intramolecular environment of the hydroxyl group in several compounds related to fats has been investigated by infrared measurements of the fundamental stretching vibration, using a lithium fluoride double monochromator and sufficiently low concentrations (.001舑.05 M) in carbon tetrachloride to avoid intermolecular effects. In saturated alcohols and saturated hydroxyl derivatives of esters, the OH stretching frequency is found to depend on the number of hydrogen and carbon atoms which form the immediate environment of the OH group. Since this varies with rotational isomerism about the C‐O single bond, the infrared hydroxyl band is composite, made up of components whose strengths give information about the relative amount of each rotational isomer present. In unsaturated alcohols and unsaturated hydroxy‐esters, rotational isomers permitting hydrogen bonding to ॠ‐electrons are stabilized according to the accessibility of the unsaturated link to the hydroxyl group, thus altering the proportions of the rotational isomers.