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.
TY - 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 . .
