Effects of ortho-Substituents in Protonolysis of Arylmercuric Chlorides with Hydrochloric Acid

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Title:Effects of ortho-Substituents in Protonolysis of Arylmercuric Chlorides with Hydrochloric Acid
Creators:
Wang, Yulan
Wu, Yangjie
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 1, pp. 35-46
Uncontrolled Keywords:Mercury, Protonolysis, Reaction kinetics, Arylmercuric halides, Substituent effects

Abstract

The kinetics of reaction of <i>ortho</i>-substituted phenylmercuric chlorides, 2-R-C<sub>6</sub>H<sub>4</sub>HgCl (R = H, CH<sub>3</sub>, CH<sub>3</sub>O, C<sub>2</sub>H<sub>5</sub>O, CF<sub>3</sub>, COOC<sub>2</sub>H<sub>5</sub>, Cl, Br, F, NO<sub>2</sub>), with hydrochloric acid in absolute ethanol in the presence of sodium iodide has been studied. The reaction is of the overall second order, first order with respect to each reactant. The rate constant determined at a fixed temperature decreases in the order of R: C<sub>2</sub>H<sub>5</sub>O &gt; CH<sub>3</sub>O &gt; CH<sub>3</sub> &gt; H &gt; COOC<sub>2</sub>H<sub>5</sub> &gt; F &gt; Cl &gt; Br &gt; CF<sub>3</sub> &gt; NO<sub>2</sub>. The role of inductive, resonance and field effects of the <i>ortho</i>-substituents, and the relation between steric demands of the <i>ortho</i>-substituents and volume of attacking species are discussed. The underlying mechanism is proposed on the basis of experimental results. <p>

Title:Effects of ortho-Substituents in Protonolysis of Arylmercuric Chlorides with Hydrochloric Acid
Creators:
Wang, Yulan
Wu, Yangjie
Uncontrolled Keywords:Mercury, Protonolysis, Reaction kinetics, Arylmercuric halides, Substituent effects
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:1
Page Range:pp. 35-46
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000035UNSPECIFIED
ID Code:1621
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Wang, Yulan; Wu, Yangjie (2000) Effects of ortho-Substituents in Protonolysis of Arylmercuric Chlorides with Hydrochloric Acid. Collection of Czechoslovak Chemical Communications, 65 (1). pp. 35-46. ISSN 0010-0765

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