Synthesis and self-assembling properties on gold of 2-methyl-1,4-naphthoquinone derivatives containing ω-mercaptoalkylalkanoate groups

Kažem≐kait≐, Maryt≐; Bulovas, Arūnas; Talaikyt, Zita; Butkus, Eugenijus; Railait, Vilma; Niaura, Gediminas; Palaima, A. I.; Razumas, Valdemaras

doi:10.1016/j.tetlet.2004.03.059

Cited by 14 publications

(2 citation statements)

References 21 publications

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“…It is apparent that PCET systems are still in need of extensive experimental exploration to resolve the numerous anomalies and to guide theoretical treatments. These types of experiments should be extended to more biologically relevant redox systems, such as the quinones − and catechols. A potential benefit may be the rational design of electrocatalysts for enhancing the rate constants for PCET.…”

Section: Discussionmentioning

confidence: 99%

Potential-, pH-, and Isotope-Dependence of Proton-Coupled Electron Transfer of an Osmium Aquo Complex Attached to an Electrode

2006

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An osmium complex, [OsII(bpy)2(4-aminomethylpyridine)(H2O)]2+, is attached to a mixed self-assembled monolayer on a gold electrode. The complex exhibits 1-electron, 1-proton redox chemistry (OsIII(OH)/OsII(H2O)) at pHs and potentials that are experimentally accessible with gold electrodes in aqueous electrolytes. The thermodynamic behavior and kinetic behavior of the system are investigated as a function of pH in both H2O and D2O. The two formal potentials and two pKa values are relatively constant for two chain lengths in H2O and in D2O. The standard rate constants at all pHs are strongly and uniformly affected by chain length, indicating that electronic coupling is the dominant factor controlling the rate of electron transfer. In both H2O and D2O, the standard rate constant is weakly dependent on the pH, exhibiting a minimum value midway between the pKa values. The kinetic isotope effect is small; standard rate constants decrease by roughly a factor of 2 in D2O over a wide range of pHs, but not at the more acidic pHs. The Tafel plots and plots of the transfer coefficient vs overpotential are asymmetrical at all pHs. These results are interpreted in terms of a larger reorganization energy for the OsII species and a smaller reorganization energy for the OsIII species. The OsIII reorganization energy is constant at all pHs in both H2O and D2O. The pH dependence of the OsII reorganization energy accounts for some or all of the pH dependence of the standard rate constant in H2O and D2O. The data deviate substantially from predictions of the stepwise proton-coupled electron-transfer mechanism. The observation of a kinetic isotope effect supports the concerted mechanism.

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Section: Discussionmentioning

confidence: 99%

Potential-, pH-, and Isotope-Dependence of Proton-Coupled Electron Transfer of an Osmium Aquo Complex Attached to an Electrode

2006

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“…The inventions of providing novel quinone derivatives having a large absorption coefficient to be used as a dichroic dye still continue . Because of these important properties, they have many applications in synthetic organic chemistry .…”

Section: Introductionmentioning

confidence: 99%

The Synthesis, Spectral, and Electrochemical Characterization of Novel Alkoxybenzoquinone Derivatives

Ibis

Ayla

Cakan

2015

Journal of Heterocyclic Chem

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The novel monosubstituted benzoquinone compounds 3e, 3g, 3h; 2,5‐O‐ substituted benzoquinone compounds 4a, 4b, 4c, 4d, 4e 4g and known compound 4h and 2,6‐O‐ substituted benzoquinone compounds 5e, 5f, 5g, 5h were obtained by the reaction of p‐chloranil (1) and related alcohol compounds in potassium carbonate (K2CO3) solution of acetonitrile or chloroform with Et3N. The novel cyclic compounds 7,8 and 10,11 were obtained from the reaction of p‐chloranil (1) and diols in potassium carbonate (K2CO3) solution of acetonitrile at room temperature. The structures of novel compounds were characterized by using micro analysis, FT‐IR, 1H‐NMR, 13C‐NMR, MS and cyclic voltammetry.

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Electron Transfer

Finklea¹

2007

Encyclopedia of Electrochemistry

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The sections in this article are Self‐assembled Monolayers ( SAMs ) Blocking SAMs , Pinholes, and Defects Electroactive SAMs Theoretical Model for Electron Transfer Measurements of Kinetic Parameters Electronic Coupling versus Distance Electronic Coupling versus Other Factors Reorganization Energies Future Directions

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Synthesis and self-assembling properties on gold of 2-methyl-1,4-naphthoquinone derivatives containing ω-mercaptoalkylalkanoate groups

Cited by 14 publications

References 21 publications

Potential-, pH-, and Isotope-Dependence of Proton-Coupled Electron Transfer of an Osmium Aquo Complex Attached to an Electrode

Potential-, pH-, and Isotope-Dependence of Proton-Coupled Electron Transfer of an Osmium Aquo Complex Attached to an Electrode

The Synthesis, Spectral, and Electrochemical Characterization of Novel Alkoxybenzoquinone Derivatives

Electron Transfer

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