Mercaptotriazole as a nucleophile in addition to o-quinone electrochemically derived from catechol: Application to electrosynthesis of a new group of triazole compounds

Shahrokhian, S ; Sharif University of Technology | 2005

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  1. Type of Document: Article
  2. DOI: 10.1016/j.elecom.2004.11.010
  3. Publisher: 2005
  4. Abstract:
  5. Electrochemical oxidation of catechol in the presence of 3-mercapto-1,2,4-triazole (MTA) as a nucleophile in aqueous buffered solutions was studied by cyclic voltammetry and controlled-potential coulometry. The mechanism of electrochemical reaction is confirmed by spectrophotometric tracing in various times of controlled-potential coulometry. The voltammetric and spectrophotometric foundations indicate that a 1,4 Michael addition of MTA from its thiol moiety to the electrochemically derived o-quinone is occurred. The electrochemical synthesis of Michael addition product has been successfully accomplished by controlled-potential coulometry in a divided H-type cell and the reaction product was characterized by spectrophotometric, 1H and 13C NMR, elemental analysis and mass spectrometric methods. © 2004 Elsevier B.V. All rights reserved
  6. Keywords:
  7. Controlled potential coulometry ; Electrochemical oxidation ; Calorimetry ; Cyclic voltammetry ; Electrochemistry ; Nuclear magnetic resonance spectroscopy ; Oxidation ; Spectrophotometry ; Synthesis (chemical) ; Organic compounds ; Catechol ; Quinone derivative ; Triazole derivative ; Analytic method ; Carbon nuclear magnetic resonance ; Coulometry ; Cyclic potentiometry ; Drug synthesis ; Mass spectrometry ; Michael addition ; proton nuclear magnetic resonance
  8. Source: Electrochemistry Communications ; Volume 7, Issue 1 , 2005 , Pages 68-73 ; 13882481 (ISSN)
  9. URL: https://www.sciencedirect.com/science/article/pii/S1388248104003042