Journal Article

Study of the Racemization Observed in the Amide Bond Forming Reaction on Silica Gel

Amanda L. Norick and Tingyu Li

in Journal of Chromatographic Science

Volume 43, issue 10, pages 526-529
Published in print November 2005 | ISSN: 0021-9665
Published online November 2005 | e-ISSN: 1945-239X | DOI:

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Racemization resulting from the coupling of N(3,5- dinitrobenzoyl)-l-leucine and 3-aminopropyl silica gel with several amide-coupling reagents is further investigated in order to explain the much higher degree of racemization on silica gel, as compared with the similar reaction in solution. Based on experiments using different types of solid supports, limited pore access and surface microchemical environment are ruled out as the possible reason for the higher degree of racemization that occurred on silica gel. Steric hindrance of the solid support is thought to have caused the amino group to be more basic relative to its nucleophilicity, leading to a higher degree of racemization.

Journal Article.  0 words. 

Subjects: Chemistry