Interaction of phenylated carboxylic acids with a conjugated imine in a study of a model of rhodopsin

Seven carboxylic acids containing a phenyl or a phenolic group and three acrylic acid derivatives were mixed in equimolar concentrations with a dienylidene Schiff base in chloroform. UV and 1H NMR (400 MHz) spectra indicated that the phenyl and the phenolic groups could not red-shift the Schiff base...

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Bibliographic Details
Published inChemical physics letters Vol. 111; no. 4; pp. 501 - 505
Main Authors Le Thanh, Hoa, Vocelle, Daniel
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier B.V 01.01.1984
Elsevier Science
Subjects
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Benzoic acid
Rhodopsin
Acetylenic compound
Aliphatic compound
Saturated compound
Dissociation constant
NMR spectrometry
Ultraviolet spectrometry
Aldimine
Organic solvent
Carboxylic acid
Model compound
Conjugated dienic compound
Protonation
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Summary:Seven carboxylic acids containing a phenyl or a phenolic group and three acrylic acid derivatives were mixed in equimolar concentrations with a dienylidene Schiff base in chloroform. UV and 1H NMR (400 MHz) spectra indicated that the phenyl and the phenolic groups could not red-shift the Schiff base absorption band but could interact with the imine by their carboxylic function through a hydrogen bridge. Of all the acids studied, only phenylpropiolic acid could protonate the Schiff base.
ISSN:0009-2614
1873-4448
DOI:10.1016/0009-2614(84)85548-7