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Theoretical and experimental study on the reactivity of methyl dichlorobenzoates with sulfur-centered nucleophiles by electron transfer reactions
Authors:Jorge G. Uranga  Juan P. Montañez  Ana N. Santiago
Affiliation:INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina
Abstract:Reactions of methyl 2,5-dichlorobenzoate or methyl 3,6-dichloro-2-methoxybenzoate with sulfur-centered nucleophiles gave mono- and disubstitution products, respectively through SRN1 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.
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