Issue 5, 2012
From the journal:

Organic & Biomolecular Chemistry

Revisiting the reaction of hydroxyl radicals with vicinal diols in water†

Dong Jiang,a   Sebastián Barata-Vallejo,‡b   Bernard T. Golding,*a   Carla Ferrerib  and  Chryssostomos Chatgilialoglu*b  

* Corresponding authors

a School of Chemistry, Newcastle University, Newcastle upon Tyne, UK
E-mail: b.t.golding@newcastle.ac.uk
Fax: +44 (0)191 222 6929
Tel: +44 (0)191 222 6647

b ISOF, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, I-40129 Bologna, Italy
E-mail: chrys@isof.cnr.it
Fax: +39 051 639 8349
Tel: +39 051 639 8309

Abstract

The carbonyl products of the reactions of hydroxyl radicals with three vicinal diols (ethane-1,2-diol, propane-1,2-diol and butane-2,3-diol) have been identified and quantified. Hydroxyl radicals were produced by γ-radiolysis of N2O-saturated aqueous solutions. The reactions result in the formation of alkoxyl radicals (∼15%) followed by β-fragmentation, and α-hydroxyl alkyl radicals that undergo H2O elimination. The latter process is part of a radical chain reaction at higher diol concentrations.

Graphical abstract: Revisiting the reaction of hydroxyl radicals with vicinal diols in water

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Article information

DOI
https://doi.org/10.1039/C1OB06538F
Article type
Paper
Submitted
07 Sep 2011
Accepted
26 Oct 2011
First published
27 Oct 2011

Org. Biomol. Chem., 2012,10, 1102-1107

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Revisiting the reaction of hydroxyl radicals with vicinal diols in water

D. Jiang, S. Barata-Vallejo, B. T. Golding, C. Ferreri and C. Chatgilialoglu, Org. Biomol. Chem., 2012, 10, 1102 DOI: 10.1039/C1OB06538F

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