Hydrogen bonding effects on the association processes between chloranil and a series of amides

Gómez, Martı́n; Gómez-Castro, Carlos Z.; Padilla‐Martínez, Itzia I.; Martínez‐Martínez, Francisco J.; González, Felipe J.

doi:10.1016/j.jelechem.2003.12.037

Cited by 48 publications

(36 citation statements)

References 35 publications

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“…The ability of Brønsted acids to modulate the redox properties of quinones has long been recognized and has been the subject of extensive study [237][238][239][240][241]. Selected examples relevant to synthetic applications are discussed below.…”

Section: Quinonesmentioning

confidence: 99%

Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Miller

Tarantino

Knowles

2016

Topics in Current Chemistry Collections

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Proton-coupled electron transfers (PCETs) are unconventional redox processes in which both protons and electrons are exchanged, often in a concerted elementary step. While PCET is now recognized to play a central a role in biological redox catalysis and inorganic energy conversion technologies, its applications in organic synthesis are only beginning to be explored. In this chapter we aim to highlight the origins, development and evolution of PCET processes most relevant to applications in organic synthesis. Particular emphasis is given to the ability of PCET to serve as a non-classical mechanism for homolytic bond activation that is complimentary to more traditional hydrogen atom transfer processes, enabling the direct generation of valuable organic radical intermediates directly from their native functional group precursors under comparatively mild catalytic conditions. The synthetically advantageous features of PCET reactivity are described in detail, along with examples from the literature describing the PCET activation of common organic functional groups.

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Section: Quinonesmentioning

confidence: 99%

Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Miller

Tarantino

Knowles

2016

Topics in Current Chemistry Collections

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“…16,18,19 It was also observed that in the accessible potential scale, the position of wave I-II is only marginally modified, whereas the wave III-IV is clearly shifted toward less negative potentials (III'-IV'). These results can be interpreted in terms of the intervention of hydrogen bonding association between CH and the reduced species Q .…”

Section: Electrochemical Reduction Of 14-benzoquinone (Q) In the Prementioning

confidence: 91%

“…− /Q 2− ), the large shift observed between waves III-IV and III'-IV', point out to a very strong hydrogen bonding association between Q 2− and CH. 18 (CH), whose voltammetric formation wave III' is limited by the diffusion-controlled availability of CH. 18 Additionally, in Figure 1 it is also observed that the intensity of prewave III´-IV´ increases and is shifted toward less negative potentials with the increase in the concentration of CH.…”

Section: Electrochemical Reduction Of 14-benzoquinone (Q) In the Prementioning

confidence: 99%

“…18 (CH), whose voltammetric formation wave III' is limited by the diffusion-controlled availability of CH. 18 Additionally, in Figure 1 it is also observed that the intensity of prewave III´-IV´ increases and is shifted toward less negative potentials with the increase in the concentration of CH. This behavior is indicative of a second association process occurring between the complex Q 2− (CH) and CH, which affords the complex Q 2− (CH) 2 (eq.…”

Section: Electrochemical Reduction Of 14-benzoquinone (Q) In the Prementioning

confidence: 99%

“…5). 15,18 The proposal of this 1:2 complex appears likely in view of the fact that the quinone dianion contains two negative oxygen atoms with which the hydrogen bonding interactions with CH can occur. Because of steric hindrance, higher association stoichiometries are less likely.…”

Section: Electrochemical Reduction Of 14-benzoquinone (Q) In the Prementioning

confidence: 99%

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Interaction of the reduced species of 1,4-benzoquinone with alkylated cytosine and guanine nucleobases

Salas

Gordillo

González

2005

Arkivoc

Self Cite

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The interaction of the reduced species of 1,4-benzoquinone (Q) in the presence of 1-octylcytosine and 9-ethylguanine has been studied in dimethylsulfoxide on glassy carbon electrodes. The electrochemical behavior showed that the semiquinone (Q .− ) and the quinone dianion (Q 2− ) interact with 1-octylcytosine (CH) according to a mechanism which involves only hydrogen bonding process. Contrasting with this mechanism, the nucleobase 9-ethylguanine (GH) leads to protonation of the semiquinone or the dianion, depending on the time scale of the voltammetric experiment. The 9-ethylguanine anion (G − ), formed in the proton transfer reactions, activates a homogeneous chain mechanism giving rise to the spontaneous redox consumption of benzoquinone and the radical consumption of the 9-ethylguanine.

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General Aspects of Redox Chemistry

González¹,

Frontana

Gómez

et al. 2016

Encyclopedia of Physical Organic Chemistry, 5 Volume Set

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Hydrogen bonding effects on the association processes between chloranil and a series of amides

Cited by 48 publications

References 35 publications

Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Interaction of the reduced species of 1,4-benzoquinone with alkylated cytosine and guanine nucleobases

General Aspects of Redox Chemistry

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