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Issue 21, 2011
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Controlling the action of chlorine radical: from lab to environment

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Abstract

The strength of Bz—Cl˙ complexation has been explored using density functional theory (DFT) calculations, including dispersion-corrected (DFT-D) calculations. Of the methods tested, the ωB97X-D method seems the best performing, along with the previously tested MPW1K method. The effect of substituent (X = NO2, F, Cl, Br, H, CH3, OCH3, OH, NH2 and N(CH3)2) on the stabilities of the Ar—Cl˙ π-like intermediates show a good correlation with the linear free energy relationships used experimentally, but this is not the case for Ar—Cl˙ σ-complexes, suggesting the transition state of abstraction as being π-like in nature. The role of PAH and lignin derivatives in mediating chlorination reactions in nature is explored. Stable π-complexes were identified for lignin derivatives, indicating humic substances may mediate chlorine atom reactivity at the marine boundary layer, in addition to forming chlorolignins.

Graphical abstract: Controlling the action of chlorine radical: from lab to environment

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Supplementary files

Article information


Submitted
02 Jan 2011
Accepted
15 Aug 2011
First published
16 Aug 2011

Org. Biomol. Chem., 2011,9, 7439-7447
Article type
Paper

Controlling the action of chlorine radical: from lab to environment

A. K. Croft, H. M. Howard-Jones, C. E. Skates and C. C. Wood, Org. Biomol. Chem., 2011, 9, 7439
DOI: 10.1039/C1OB00001B

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