Comparing the catalytic efficiency of ring substituted 1- hydroxybenzotriazoles as laccase mediators (Articolo in rivista)

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Label
  • Comparing the catalytic efficiency of ring substituted 1- hydroxybenzotriazoles as laccase mediators (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tet.2014.02.068 (literal)
Alternative label
  • C. D'Alfonso, O. Lanzalunga, A. Lapi, R. Vadala (2014)
    Comparing the catalytic efficiency of ring substituted 1- hydroxybenzotriazoles as laccase mediators
    in Tetrahedron (Oxf., Online)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • C. D'Alfonso, O. Lanzalunga, A. Lapi, R. Vadala (literal)
Pagina inizio
  • 3049 (literal)
Pagina fine
  • 3055 (literal)
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  • http://www.scopus.com/inward/record.url?eid=2-s2.0-84897544649&partnerID=q2rCbXpz (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 70 (literal)
Rivista
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  • 7 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 18 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica, Sapienza Università di Roma, IMC- Sezione Meccanismi di Reazione, P.le A. Moro 5, 00185 Roma, Italy (literal)
Titolo
  • Comparing the catalytic efficiency of ring substituted 1- hydroxybenzotriazoles as laccase mediators (literal)
Abstract
  • 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-CH3-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 CeH 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 NOeH BDE value, as assessed in this study through a radical equilibration technique. (literal)
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