Protonation of 1,3- and 1,4-dinitrobenzene dianions |
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Authors: | A S Mendkovich M A Syroeshkin L V Mikhalchenko A I Rusakov V P Gultyai |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation;(2) P. G. Demidov Yaroslavl State University, 14 ul. Sovetskaya, 150000 Yaroslavl, Russian Federation |
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Abstract: | The protonation of the electrochemically generated (0.1 M solution of tetrabutylammonium perchlorate in DMF) 1,3-dinitrobenzene (1) dianions with phenol, ethanol, tert-butanol, and 1-butyl-3-methylimidazolium cation was studied by cyclic voltammetry and chronoamperometry at the carbositall
working electrode. The rate constants for the protonation (k) of the dianion of compound 1 by phenol, 1-butyl-3-methylimidazolium cation, ethanol, and tert-butanol were estimated by the comparison of the data of cyclic voltammetry and chronoamperometry with the digital simulation
results, being 100, 50, 1.5, and 0.01 L mol−1 s−1, respectively. The similarly obtained k value for the protonation of the dianion of 1,4-dinitrobenzene (2) with phenol is 13 L mol−1 s−1. According to the quantum chemical calculation results, the protonation of the dianions of compounds 1 and 2 with phenol and 1-butyl-3-methylimidazolium cation can be classified as orbital-controlled reactions.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1463–1466, July, 2008. |
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Keywords: | electrochemical reduction 1 3-dinitrobenzene 1 4-dinitrobenzene protonation phenol 1-butyl-3-methylimidazolium tetrafluoroborate |
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