Structure dependence in the solvolysis kinetics of amino acid esters |
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Authors: | John Haseltine |
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Institution: | Department of Chemistry and Biochemistry, Kennesaw State University, Kennesaw, GA 30144, USA |
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Abstract: | To better understand acyl transfer reactions of oligopeptides, seventeen N-acyl amino acid esters were solvolyzed in mildly basic methanol-d4. All show pseudo-first-order kinetics by 1H NMR. The rate constant varies up to 400-fold with the identity of the amino acid and up to 6200-fold with the identity of the N-acyl group. The impact of the N-acyl group on the rate constant is discussed in terms of crowding, amide conformation, and amide C O bond character. |
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Keywords: | Amino acid esters Acyl transfer Crowded amides Amide polarity |
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