α-Substitution Effects on the Ease of SN-Acyl Transfer in Aminothioesters

Authors

  • Bahaa El-Dien M. El-Gendy,

    1. Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611-7200, USA
    2. Department of Chemistry, Faculty of Science, Benha University, PO Box 13511 Benha, Egypt
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  • Ebrahim H. Ghazvini Zadeh,

    1. Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611-7200, USA
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  • Ania C. Sotuyo,

    1. Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611-7200, USA
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  • Girinath G. Pillai,

    1. Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611-7200, USA
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  • Alan R. Katritzky

    Corresponding author
    1. Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611-7200, USA
    2. Department of Chemistry, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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*Corresponding author: Alan R. Katritzky,katritzky@chem.ufl.edu

Abstract

In S-acylcysteines and homocysteines, the efficacy and rate of SN-acyl transfer (5 and 6 cyclic TSs) vary with the size of S-acyl group. Conformational and quantum chemical calculations indicate that the spatial distance, b(N-C), between the terminal amine and the thioester carbon is shortened by α-C(O)X (X = OH, OMe, NH2) substituents.

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