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Comparing the catalytic efficiency of ring substituted 1-hydroxybenzotriazoles as laccase mediators

Tetrahedron, ISSN: 0040-4020, Vol: 70, Issue: 18, Page: 3049-3055
2014
  • 17
    Citations
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  • 20
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Metrics Details

  • Citations
    17
    • Citation Indexes
      17
  • Captures
    20

Article Description

A series of ring substituted 1-hydroxybenzotriazoles (6-X-HBTs) have been tested as mediators in the laccase-promoted oxidation of 4-methoxybenzyl alcohol, 3,4-dimethoxybenzyl alcohol, and the dimeric lignin model 1-(3,4-dimethoxyphenyl)-2-phenoxyethanol. The effect of the aryl substituents on the yields of oxidation products is remarkable. The catalytic mediation efficiency increases as the electron releasing (ER) properties of the substituent increases up to a maximum value for 6-CH 3 -HBT, which resulted a very efficient mediator. Both the oxidation of the 6-X-HBTs to the N -oxyl radicals (6-X-BTNO) by laccase and the hydrogen atom transfer (HAT) process from the benzylic C–H to the 6-X-BTNO contribute to the overall reactivity. The former process is favored by ER substituents that lower the mediator redox potentials. On the other hand, ER substituents decrease the 6-X-BTNO reactivity in the HAT process due to a decrease in the NO–H BDE value, as assessed in this study through a radical equilibration technique.

Bibliographic Details

Claudio D'Alfonso; Osvaldo Lanzalunga; Andrea Lapi; Raffaella Vadalà

Elsevier BV

Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Chemistry

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