Theoretical and experimental study on the reactivity of methyl dichlorobenzoates with sulfur-centered nucleophiles by electron transfer reactions

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• 作者：Jorge G. Uranga ; Juan P. Montañ ; ez ; Ana N. Santiago  ; ;   ; ^{santiago@fcq.unc.edu.ar}
• 关键词：Electron transfer ; Herbicide ; Thiolate group ; DFT
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：14 January 2012
• 年：2012
• 卷：68
• 期：2
• 页码：584-589
• 全文大小：597 K

文摘

Reactions of methyl 2,5-dichlorobenzoate or methyl 3,6-dichloro-2-methoxybenzoate with sulfur-centered nucleophiles gave mono- and disubstitution products, respectively through S_RN1 mechanism in liquid ammonia. Products obtained could be potential herbicides less toxic to the environment. Theoretical studies explained the reactivity observed considering geometries, and spin densities of radical anions and potential energy surfaces for the dissociation of the radical anions formed.