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Reference type: Journal
Authors: Morihara K, Tanaka E, Takeuchi Y, Miyazaki K, Yamamoto N, Sagawa Y, Kawamoto E, Shimada T
Article Title: Footprint catalysis .3. Inducible alteration of substrate specificities of silica(alumina) gel catalysts for 2,4-dinitrophenolysis of toluic anhydrides by footprint imprinting.
Publication date: 1989
Journal: Bulletin of the Chemical Society of Japan
Volume: 62
Issue: (2)
Page numbers: 499-505.
DOI: 10.1246/bcsj.62.499

Abstract: A tailor-made catalyst design was attempted for a required substrate specificity by the authors' footprint imprinting method. Two silica(alumina) footprint catalysts were prepared by imprinting with N-benzoylbenzenesulfonamide (1) and N-(p-toluoyl)-p-toluenesulfonamide (2) from the same aluminum ion-doped silica gel. Their catalytic effects upon 2,4-dinitrophenolysis of benzoic anhydride, p-, m-, and o-toluic anhydrides were compared in order to find any difference in substrate specificities. The catalyst prepared by imprinting with 1 showed the largest specificity(kcat/Km) toward benzoic anhydride, whereas the catalyst prepared with 2 showed the largest specificity toward p-toluic anhydride. This finding evidently demonstrated that the substrate specificities of footprint catalytic sites are alterable, as required through selecting appropriate transition state analogs as template molecules for footprint marking.

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