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On the Nucleophilic Reactivity of 4,6-Dichloro-5-nitrobenzofuroxan with Some Aliphatic and Aromatic Amines: Selective Nucleophilic Substitution.
Chugunova, Elena; Frenna, Vincenzo; Consiglio, Giovanni; Micheletti, Gabriele; Boga, Carla; Akylbekov, Nurgali; Burilov, Alexander; Spinelli, Domenico.
Afiliação
  • Chugunova E; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov Street 8, 420088 Kazan, Tatarstan, Russia.
  • Frenna V; Laboratory of Plant Infectious Diseases, FRC Kazan Scientific Center of Russian Academy of Sciences, Lobachevskogo Street 2/31, 420111 Kazan, Tatarstan, Russia.
  • Consiglio G; Department STEBICEF, Università di Palermo, Viale delle Scienze-Parco d'Orleans II, 90128 Palermo, Italy.
  • Micheletti G; Department of Chemistry 'G. Ciamician', Alma Mater Studiorum-Università di Bologna, Via Selmi 2, 40126 Bologna, Italy.
  • Boga C; Department of Industrial Chemistry 'Toso Montanari', Alma Mater Studiorum-Università di Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
  • Akylbekov N; Department of Industrial Chemistry 'Toso Montanari', Alma Mater Studiorum-Università di Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
  • Burilov A; Korkyt Ata Kyzylorda University, Aiteke bie Street, 29A, 120014 Kyzylorda, The Republic of Kazakhstan.
  • Spinelli D; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov Street 8, 420088 Kazan, Tatarstan, Russia.
J Org Chem ; 85(21): 13472-13480, 2020 11 06.
Article em En | MEDLINE | ID: mdl-33153266
The reaction rates for the nucleophilic aromatic substitution of 4,6-dichloro-5-nitrobenzofuroxan 1 with eight aliphatic amines (characterized by very different basicities/nucleophilicities) and three anilines have been measured in both methanol and toluene. The obtained rates have been related to the basicity (pKaH in water and Kb in benzene) or nucleophilicity (N Mayr constants) of the tested amines. The whole of the obtained kinetic data has furnished useful information on the high nucleophilic reactivity of benzofuroxan derivatives, which has been related essentially to two factors: the high electron-drawing ability/power of the condensed furoxan ring and the low aromatic character of the benzofuroxan system.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Federação Russa

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Federação Russa