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Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles. / Shundrin, Leonid A.; Irtegova, Irina G.; Avrorov, Pavel A. et al.

In: Arkivoc, Vol. 2017, No. 3, 25.06.2017, p. 166-180.

Research output: Contribution to journal › Article › peer-review

Harvard

Shundrin, LA, Irtegova, IG, Avrorov, PA, Mikhailovskaya, TF, Makarov, AG, Makarov, AY & Zibarev, AV 2017, 'Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles', Arkivoc, vol. 2017, no. 3, pp. 166-180. https://doi.org/10.3998/ark.5550190.p010.116

APA

Shundrin, L. A., Irtegova, I. G., Avrorov, P. A., Mikhailovskaya, T. F., Makarov, A. G., Makarov, A. Y., & Zibarev, A. V. (2017). Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles. Arkivoc, 2017(3), 166-180. https://doi.org/10.3998/ark.5550190.p010.116

Vancouver

Shundrin LA, Irtegova IG, Avrorov PA, Mikhailovskaya TF, Makarov AG, Makarov AY et al. Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles. Arkivoc. 2017 Jun 25;2017(3):166-180. doi: 10.3998/ark.5550190.p010.116

Author

Shundrin, Leonid A. ; Irtegova, Irina G. ; Avrorov, Pavel A. et al. / Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles. In: Arkivoc. 2017 ; Vol. 2017, No. 3. pp. 166-180.

BibTeX

@article{fbcf967fb921414f8d0e1cc1d1a80508,
title = "Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles",
abstract = "At the first stage of electrochemical reduction in DMF, fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles formed long-lived radical anions characterized by EPR and DFT. Gas-phase electron affinities (EA1) from DFT correlated well with the first-peak potentials separately for S and Se derivatives, and the latter were found to be better electron acceptors than the former in contrast to the atomic EA1 and Allen electronegativity. At the second stage, chalcogen-and halogen-dependent dehalogenation proceeded: non-hydrodefluorination of selenadiazoles through their n-electron activation (n ≥ 2), and hydrodechlorination of thia/selenadiazoles through H+ addition to their dianions. These differ from dehalogenation of related (aza) aromatics (e.g. benzenes, naphthalenes, quinoxalines).",
keywords = "2,1,3-benzoselenadiazoles, 2,1,3-Benzothiadiazoles, Chlorinated, Cyclic voltammetry, Dehalogenation, DFT, EPR, Fluorinated, Radical anions",
author = "Shundrin, {Leonid A.} and Irtegova, {Irina G.} and Avrorov, {Pavel A.} and Mikhailovskaya, {Tatiana F.} and Makarov, {Arkady G.} and Makarov, {Alexander Yu} and Zibarev, {Andrey V.}",
year = "2017",
month = jun,
day = "25",
doi = "10.3998/ark.5550190.p010.116",
language = "English",
volume = "2017",
pages = "166--180",
journal = "Arkivoc",
issn = "1551-7004",
publisher = "Arkat USA",
number = "3",

}

RIS

TY - JOUR

T1 - Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles

AU - Shundrin, Leonid A.

AU - Irtegova, Irina G.

AU - Avrorov, Pavel A.

AU - Mikhailovskaya, Tatiana F.

AU - Makarov, Arkady G.

AU - Makarov, Alexander Yu

AU - Zibarev, Andrey V.

PY - 2017/6/25

Y1 - 2017/6/25

N2 - At the first stage of electrochemical reduction in DMF, fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles formed long-lived radical anions characterized by EPR and DFT. Gas-phase electron affinities (EA1) from DFT correlated well with the first-peak potentials separately for S and Se derivatives, and the latter were found to be better electron acceptors than the former in contrast to the atomic EA1 and Allen electronegativity. At the second stage, chalcogen-and halogen-dependent dehalogenation proceeded: non-hydrodefluorination of selenadiazoles through their n-electron activation (n ≥ 2), and hydrodechlorination of thia/selenadiazoles through H+ addition to their dianions. These differ from dehalogenation of related (aza) aromatics (e.g. benzenes, naphthalenes, quinoxalines).

AB - At the first stage of electrochemical reduction in DMF, fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles formed long-lived radical anions characterized by EPR and DFT. Gas-phase electron affinities (EA1) from DFT correlated well with the first-peak potentials separately for S and Se derivatives, and the latter were found to be better electron acceptors than the former in contrast to the atomic EA1 and Allen electronegativity. At the second stage, chalcogen-and halogen-dependent dehalogenation proceeded: non-hydrodefluorination of selenadiazoles through their n-electron activation (n ≥ 2), and hydrodechlorination of thia/selenadiazoles through H+ addition to their dianions. These differ from dehalogenation of related (aza) aromatics (e.g. benzenes, naphthalenes, quinoxalines).

KW - 2,1,3-benzoselenadiazoles

KW - 2,1,3-Benzothiadiazoles

KW - Chlorinated

KW - Cyclic voltammetry

KW - Dehalogenation

KW - DFT

KW - EPR

KW - Fluorinated

KW - Radical anions

UR - http://www.scopus.com/inward/record.url?scp=85021672416&partnerID=8YFLogxK

U2 - 10.3998/ark.5550190.p010.116

DO - 10.3998/ark.5550190.p010.116

M3 - Article

AN - SCOPUS:85021672416

VL - 2017

SP - 166

EP - 180

JO - Arkivoc

JF - Arkivoc

SN - 1551-7004

IS - 3

ER -

ID: 10097176