Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents
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2011
Authors
Šegan, Dejan M.Vukicevic, Rastko D.
Šegan, Sandra B.
Šojić, Nešo
Buriez, Olivier
Manojlović, Dragan D.
Article (Published version)
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Cyclic voltammetry and ultramicroelectrodes were used to investigate the kinetic aspects of the electrochemical bromination of 3,4,6-tri-O-acetyl-D-glucal (1) in acetonitrile (AN), dichloromethane (DCM), and dimethylsulfoxide (DMSO). Qualitative and quantitative results, determined notably from the kinetic parameter [glucal]/nu representing the competition between glucal concentration and time, clearly showed that glucal bromination depended on the nature of both the solvent and the in situ electrogenerated reactive brominated species (Br-2 or Br-3(-)) obtained from the oxidation of a bromide salt. It was especially shown that Br-2 reacted more rapidly than Br-3(-) towards (1). On the other hand, the reactivity of both brominated species appeared to follow the solvent polarity order since the highest reactivity was obtained in DMSO whereas the lowest one was found in DCM. (C) 2011 Elsevier Ltd. All rights reserved.
Keywords:
Kinetic / Bromination / Glycal / Cyclic voltammetrySource:
Electrochimica Acta, 2011, 56, 27, 9968-9972Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Ministry of Science of the Republic of Serbia
DOI: 10.1016/j.electacta.2011.08.085
ISSN: 0013-4686
WoS: 000297399100040
Scopus: 2-s2.0-80054931632
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Šegan, Dejan M. AU - Vukicevic, Rastko D. AU - Šegan, Sandra B. AU - Šojić, Nešo AU - Buriez, Olivier AU - Manojlović, Dragan D. PY - 2011 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1222 AB - Cyclic voltammetry and ultramicroelectrodes were used to investigate the kinetic aspects of the electrochemical bromination of 3,4,6-tri-O-acetyl-D-glucal (1) in acetonitrile (AN), dichloromethane (DCM), and dimethylsulfoxide (DMSO). Qualitative and quantitative results, determined notably from the kinetic parameter [glucal]/nu representing the competition between glucal concentration and time, clearly showed that glucal bromination depended on the nature of both the solvent and the in situ electrogenerated reactive brominated species (Br-2 or Br-3(-)) obtained from the oxidation of a bromide salt. It was especially shown that Br-2 reacted more rapidly than Br-3(-) towards (1). On the other hand, the reactivity of both brominated species appeared to follow the solvent polarity order since the highest reactivity was obtained in DMSO whereas the lowest one was found in DCM. (C) 2011 Elsevier Ltd. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Electrochimica Acta T1 - Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents VL - 56 IS - 27 SP - 9968 EP - 9972 DO - 10.1016/j.electacta.2011.08.085 ER -
@article{ author = "Šegan, Dejan M. and Vukicevic, Rastko D. and Šegan, Sandra B. and Šojić, Nešo and Buriez, Olivier and Manojlović, Dragan D.", year = "2011", abstract = "Cyclic voltammetry and ultramicroelectrodes were used to investigate the kinetic aspects of the electrochemical bromination of 3,4,6-tri-O-acetyl-D-glucal (1) in acetonitrile (AN), dichloromethane (DCM), and dimethylsulfoxide (DMSO). Qualitative and quantitative results, determined notably from the kinetic parameter [glucal]/nu representing the competition between glucal concentration and time, clearly showed that glucal bromination depended on the nature of both the solvent and the in situ electrogenerated reactive brominated species (Br-2 or Br-3(-)) obtained from the oxidation of a bromide salt. It was especially shown that Br-2 reacted more rapidly than Br-3(-) towards (1). On the other hand, the reactivity of both brominated species appeared to follow the solvent polarity order since the highest reactivity was obtained in DMSO whereas the lowest one was found in DCM. (C) 2011 Elsevier Ltd. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Electrochimica Acta", title = "Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents", volume = "56", number = "27", pages = "9968-9972", doi = "10.1016/j.electacta.2011.08.085" }
Šegan, D. M., Vukicevic, R. D., Šegan, S. B., Šojić, N., Buriez, O.,& Manojlović, D. D.. (2011). Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents. in Electrochimica Acta Pergamon-Elsevier Science Ltd, Oxford., 56(27), 9968-9972. https://doi.org/10.1016/j.electacta.2011.08.085
Šegan DM, Vukicevic RD, Šegan SB, Šojić N, Buriez O, Manojlović DD. Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents. in Electrochimica Acta. 2011;56(27):9968-9972. doi:10.1016/j.electacta.2011.08.085 .
Šegan, Dejan M., Vukicevic, Rastko D., Šegan, Sandra B., Šojić, Nešo, Buriez, Olivier, Manojlović, Dragan D., "Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents" in Electrochimica Acta, 56, no. 27 (2011):9968-9972, https://doi.org/10.1016/j.electacta.2011.08.085 . .