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Kinetics of the reaction of sodium arylthiolates with nitro-carboxybenzyl halide derivatives

✍ Scribed by Ezzat A. Hamed; Ali A. El-Bardan; Nabila M. El-Mallah

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
475 KB
Volume
28
Category
Article
ISSN
0538-8066

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✦ Synopsis

The rate constants for the reactions of 4-halomethyl-3-nitrobenzoic acids, the nonnitro derivatives, and their ethyl esters with arylthiolates were measured at different temperatures. It was found that the retardation in rate constants compared to benzyl halides is due to the electrostatic repulsion between the electronegative substituents (COO-and/or NO21 in the substrates and thiolate ions Good correlations between log k2 values of the acids and carbon basicities of thiolates were found while log k2 values of the esters show good straight lines with Harnrnett CT constants, pk,, and carbon basicities of arylthiolates. @ 1996 lohn Wiley &

Sons Inc

INTRODUCTlON

The action of sodium hydroxide on 2-nitrobenzyl chloride in aqueous dioxane gave 2,2'-dinitrostilbene via carbene formed by an a-EICB mechanism as well as a mixture of cis and trans-dinitrostilbene oxide [ I I. While 2-nitrobenzyl bromide and iodide gave 2,2'-dinitrobenzylether, under the previous conditions, through an initial slow SN2 hydrolysis step followed by a faster SN2 etherification step [ l ] . The reaction of 4-halomethyl-3-nitrobenzoic acid ( I ) and the corresponding nonnitro derivative (2) with aqueous sodium hydroxide gave a mixture of the corresponding benzyl alcohol and/or dibenzyl ether derivative depending on the type of the halogen [2].

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