Aromatic nitro substitution reaction between 4-nitro-N-n-butyl-1,8-naphthalimide and n-heptanethiol in water-methanol binary mixtures

Autor(es)

Triboni, Eduardo Rezende ^[1] ; Artur, Julio Cesar ^[2] ; Berci Filho, Pedro ^[2] ; Cuccovia, Iolanda Midea ^[1] ; Politi, Mario Jose ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim, Dept Bioquim, BR-05508900 Sao Paulo - Brazil

^[2] Univ Sao Paulo, Inst Quim Sao Carlos, Dept Quim Fis, BR-13566590 Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY; v. 22, n. 7, p. 703-708, JUL 2009.
• Citações Web of Science: 3

Resumo

The second-order rate constants of thiolysis by n-heptanethiol on 4-nitro-N-n-butyl-1,8-naphthalimide (4NBN) are strongly affected by the water-methanol binary mixture composition reaching its maximum at around 50% mole fraction. In parallel solvent effects on 4NBN absorption molar extinction coefficient also shows a maximum at this composition region. From the spectroscopic study of reactant and product and the known H-bond capacity of the mixture a rationalization that involves specific solvent H-donor interaction with the nitro group is proposed to explain the kinetic data. Present findings also show a convenient methodology to obtain strongly fluorescent imides, valuable for peptide and analogs labeling as well as for thio-naphthalimide derivatives preparations. Copyright (C) 2008 John Wiley \& Sons, Ltd. (AU)

• Processo FAPESP: 04/15069-7 - Sistemas inteligentes e sensores derivados de mono e di aralquilimidas
• Beneficiário: Eduardo Rezende Triboni
• Linha de fomento: Bolsas no Brasil - Pós-Doutorado