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Molecularly imprinted polymer catalysis of a Diels-Alder reaction
University of Kalmar, School of Pure and Applied Natural Sciences.
University of Kalmar, School of Pure and Applied Natural Sciences.
University of Kalmar, School of Pure and Applied Natural Sciences.
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2009 (English)In: Journal of Molecular Catalysis B: Enzymatic, ISSN 1381-1177, E-ISSN 1873-3158, Vol. 58, no 1-4, p. 110-117Article in journal (Refereed) Published
Abstract [en]

A series of synthetic polymers were designed and synthesized for enhancing the rate of the Diels-Alder cycloaddition reaction of 1,3-butadiene carbamic acid benzyl ester (11) and N,N-dimethyl acrylamide (2), to yield the corresponding endo- (3) and exo- (4) reaction products. Putative transition state analogues (TSAs) for the endo- (5) and exo- (6) reaction pathways were used as templates for the synthesis of molecularly imprinted methacrylic acid (MAA)-divinylbenzene (DVB) copolymers. The polymer system utilized was selected based upon a series of (1)H NMR studies of complex formation between template and a functional monomer analogue (K(d) (app) approximate to 70 mM, d(8)-toluene, 293 K). Batch binding studies revealed that the imprinted polymers were selective for the TSA corresponding to the template used in the polymer synthesis. Studies on the influence of the polymers on the catalysis of the reaction of 1 and 2 demonstrated a 20-fold enhancement of the rate of the reaction relative to the solution reaction. A surprising temperature dependence of the reaction of 1 and 2 in the presence of the polymers was observed, which provides support for the role of template-functional monomer complexes in the catalysis of the Diels-Alder reaction.

Place, publisher, year, edition, pages
2009. Vol. 58, no 1-4, p. 110-117
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry; Chemistry, Biotechnology
Identifiers
URN: urn:nbn:se:lnu:diva-1889DOI: 10.1016/j.molcatb.2008.12.002OAI: oai:DiVA.org:lnu-1889DiVA, id: diva2:308937
Available from: 2010-04-06 Created: 2010-04-06 Last updated: 2018-05-18Bibliographically approved

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Kirsch, NicoleHedin-Dahlström, JimmyHenschel, HenningWikman, SusanneNicholls, Ian A.

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Kirsch, NicoleHedin-Dahlström, JimmyHenschel, HenningWikman, SusanneNicholls, Ian A.
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Journal of Molecular Catalysis B: Enzymatic
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