Correlation Engine 2.0
Clear Search sequence regions

  • alkyl (8)
  • electrodes (1)
  • energies (2)
  • glucosides (8)
  • Sizes of these terms reflect their relevance to your search.

    A voltammetric study of a series of alkyl and aryl S-glucosides unveiled the reactivity patterns of alkyl S-glucosides toward anodic oxidation and found noteworthy differences with the trends followed by aryl derivatives. The oxidation potential of alkyl S-glucosides, estimated herein from square-wave voltammetry peak potentials (Ep), depends on the steric properties of the aglycone. Glucosides substituted with bulky groups exhibit Ep values at voltages more positive than the values of those carrying small aglycones. This relationship, observed in all analyzed alkyl series, is evidenced by good linear correlations between Ep and Taft's steric parameters (ES) of the respective alkyl substituents. Moreover, the role of the aglycone's steric properties as a primary reactivity modulator is backed by poor correlations between Ep and the radical stabilization energies (RSEs) of the aglycone-derived thiyl radicals (RS•). In contrast, aryl glucosides' Ep values exhibit excellent correlations with the aryl substituents' Hammett parameters (σ+) and the ArS• RSEs, evidencing the inherent stability of the reactive radical intermediate as the primary factor controlling aryl glucoside's electrochemical reactivity. The reactivity differences between alkyl and aryl S-glucosides also extend to the protective group's effect on Ep. Alkyl S-glucosides' reactivity proved to be more sensitive to protective group exchange.


    Bhavesh Deore, Joseph E Ocando, Lan D Pham, Carlos A Sanhueza. Anodic Reactivity of Alkyl S-Glucosides. The Journal of organic chemistry. 2022 May 06;87(9):5952-5960

    Expand section icon Mesh Tags

    Expand section icon Substances

    PMID: 35417151

    View Full Text