62020-02-4Relevant articles and documents
Substrate-Specific Heterogeneous Catalysis of CeO2 by Entropic Effects via Multiple Interactions
Tamura, Masazumi,Sawabe, Kyoichi,Tomishige, Keiichi,Satsuma, Atsushi,Shimizu, Ken-Ichi
, p. 20 - 26 (2015/04/27)
Achieving complete substrate specificity through multiple interactions like an enzyme is one of the ultimate goals in catalytic studies. Herein, we demonstrate that multiple interactions between the CeO2 surface and substrates are the origin of substrate-specific hydration of nitriles in water by CeO2, which is exclusively applicable to the nitriles with a heteroatom (N or O) adjacent to the α-carbon of the CN group but is not applicable to the other nitriles. Kinetic studies reveal that CeO2 reduces the entropic barrier (TΔS?) for the reaction of the former reactive substrate, leading to 107-fold rate enhancement compared with the latter substrate. Density functional theory (DFT) calculations confirmed multiple interaction of the reactive substrate with CeO2, as well as preferable approximation and alignment of the nitrile group of the substrate to the active OH group on CeO2 surface. This can lead to the reduction of the entropic barrier. This is the first example of an entropy-driven substrate-specific catalysis of a nonporous metal oxide surface, which will provide a new design strategy for enzyme-inspired synthetic catalysts.
Efficient and substrate-specific hydration of nitriles to amides in water by using a CeO2 catalyst
Tamura, Masazumi,Wakasugi, Hiroko,Shimizu, Ken-Ichi,Satsuma, Atsushi
supporting information; experimental part, p. 11428 - 11431 (2011/10/18)
CeO2 acted as a reusable and effective catalyst for the hydration of various nitriles to amides in water under neutral conditions at low temperature (30-100 °C). CeO2 showed notable substrate specificity for nitriles that have a heteroatom adjacent to the α-carbon atom of the CN group (see scheme).
BENZAMIDE FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS
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Page/Page column 76, (2010/09/17)
The present invention provides novel benzamide derivatives of Formula (I): or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein the variables A, W, Y, Z, R8, and R9 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.
Mild and efficient conversion of nitriles to amides with basic urea- hydrogen peroxide adduct
Balicki,Kaczmarek
, p. 3149 - 3155 (2007/10/02)
The urea-hydrogen peroxide adduct, an inexpensive, stable and easily handled reagent has shown utility for mild and efficient transformation of nitriles into the corresponding aliphatic or aromatic amides. Reaction proceeds in aqueous acetone, within 0.5-2. 5h, in the presence of catalytic amount of K2CO3, at room temperature.