FTIR studies of conformational isomerism in acrylates and acrylic acids

Acrylates have the possibility of existing in two heavy-atom planar structures (s- cis and s- trans), and research has shown that in many instances these conformations have somewhat similar energies. In the case of monomeric acrylic acid trapped in an inert matrix at low temperatures, two independen...

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Bibliographic Details
Published in:Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 1999-05, Vol.55 (5), p.1021-1024
Main Authors: Orgill, M., Baker, B.L., Owen, N.L.
Format: Article
Language:English
Subjects:
Acrylates and acrylic acids
FTIR
Matrix isolation
Rotational or conformational isomerism
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Summary:Acrylates have the possibility of existing in two heavy-atom planar structures (s- cis and s- trans), and research has shown that in many instances these conformations have somewhat similar energies. In the case of monomeric acrylic acid trapped in an inert matrix at low temperatures, two independent studies have shown that irradiation by UV light results in interconversion of the two rotamers. An interpretation of this phenomenon has been proposed in terms of hindered internal rotation about the central C–O bond. Our experimental observations on methacrylic acid (as reported in this paper), and methyl methacrylate demonstrate that the former compound shows a behavior similar to that of acrylic acid, but that UV irradiation has no effect on the interconversion of conformers in methyl methacrylate. An alternative mechanism for the interconversion of the isomers in the acrylic acids involving proton transfer is proposed.
ISSN:1386-1425
DOI:10.1016/S1386-1425(98)00242-X