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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Triboni, Eduardo Rezende [1] ; Artur, Julio Cesar [2] ; Berci Filho, Pedro [2] ; Cuccovia, Iolanda Midea [1] ; Politi, Mario Jose [1]
Total Authors: 5
[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
Total Affiliations: 2
Document type: Journal article
Source: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY; v. 22, n. 7, p. 703-708, JUL 2009.
Web of Science Citations: 3

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)