Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents
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2011
Authors
Šegan, Dejan
Vukicevic, Rastko D.
Šegan, Sandra

Šojić, Nešo

Buriez, Olivier
Manojlović, Dragan

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.
Keywords:
Kinetic / Bromination / Glycal / Cyclic voltammetrySource:
Electrochimica Acta, 2011, 56, 27, 9968-9972Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
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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IHTMTY - JOUR AU - Šegan, Dejan AU - Vukicevic, Rastko D. AU - Šegan, Sandra AU - Šojić, Nešo AU - Buriez, Olivier AU - Manojlović, Dragan PY - 2011 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/861 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. PB - Oxford : Pergamon-Elsevier Science Ltd 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 and Vukicevic, Rastko D. and Šegan, Sandra and Šojić, Nešo and Buriez, Olivier and Manojlović, Dragan", 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.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", 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., Vukicevic, R. D., Šegan, S., Šojić, N., Buriez, O.,& Manojlović, D.. (2011). Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents. in Electrochimica Acta Oxford : Pergamon-Elsevier Science Ltd., 56(27), 9968-9972. https://doi.org/10.1016/j.electacta.2011.08.085
Šegan D, Vukicevic RD, Šegan S, Šojić N, Buriez O, Manojlović D. 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, Vukicevic, Rastko D., Šegan, Sandra, Šojić, Nešo, Buriez, Olivier, Manojlović, Dragan, "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 . .