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Association of 1,4 dinitrobenzene (1,4 DNB) dianion (DA) with 1 butyl 3 methylimid azolium (bmim + ) and 1 butyl 2,3 dimethylimidazolium (bdmim + ) cations, whose salts are widely used as ionic liquids, was studied by cyclic voltammetry. In 0.1 М solution of Bu 4 NClO 4 in DMF, associates with the number of coordinated cations up to four in the case of bmim + and two in the case of bdmim + are formed. The partial stability constant values for the associates of bmim + are 40, 20, 5, and 3.2 L mol -1 , of bdmim + -24 and 1.9 L mol -1 . The higher number of coordinated bmim + cations is attributed to the formation of, along with ion pairs, hydrogen bonds between 1,4 DNB DA and bmim + due to the labile hydrogen atom at position 2 of the imidazole ring, in contrast to bdmim + , which is involved only into the ion pair interactions.Key words: 1,4 dinitrobenzene dianion, 1 butyl 3 methylimidazolium cation, 1 butyl 2,3 dimethylimidazolium cation, cyclic voltammetry, ion pairs, hydrogen bond.In the last decade, ionic liquids (IL) became widely proliferated in organic electrochemistry as electrolytes due to their good electroconductivity, wide range of potentials available for measurement, incombustibility, thermal sta bility, nonvolatility, and possibility of multiple reuse. 1a One of the most wide spread varieties of IL are 1,3 dial kylimidazolium salts. Hitherto, a number of works have been published devoted to the study of electrochemical behavior in these IL of such classes of compounds tradi tional for electroorganic chemistry as mono and poly nuclear aromatic hydrocarbons, 2,3 nitro 4-7 and carbon yl 8-13 compounds, olefins, 14 alkyl and aryl halides, 9,15 amines, 16 and many others.Efficiency of the use of IL in electroorganic chemistry will be very much determined by availability of the data on their influence, including specific, on chemical behavior of the intermediate products of electrochemical processes. In particular, in the case of electroreduction in imidazole IL, an important part should be played by the reactions of radical anions (RA) and dianions (DA) formed in the course of electrochemical process with imidazolium cat ion. A number of recently published works 4,5,17,18 are de voted to the study of such reactions using RA and DA of 1,4 dinitrobenzene (1,4 DNB) as an example.It is known 18 that cyclic voltammograms (CVA curves) of 1,4 DNB in aprotic media exhibit two well resolved and completely reversible peaks corresponding to the se quential formation of its RA and DA. The CVA curves in IL 1 butyl 3 methylimidazolium tetrafluoroborate exhib it 4,5 only one completely reversible two electron peak, i.e., an inversion of the first and second electron transfer po tentials to the 1,4 DNB molecule occurs. This effect was explained by the strong ion pair interaction between 1,4 DNB DA and 1 butyl 3 methylimidazolium cation (bmim + ). However, it is known that the inversion of the first and second electron transfer potentials to the 1,4 DNB molecule can be caused not only by the forma tion of ion pairs with ...
Association of 1,4 dinitrobenzene (1,4 DNB) dianion (DA) with 1 butyl 3 methylimid azolium (bmim + ) and 1 butyl 2,3 dimethylimidazolium (bdmim + ) cations, whose salts are widely used as ionic liquids, was studied by cyclic voltammetry. In 0.1 М solution of Bu 4 NClO 4 in DMF, associates with the number of coordinated cations up to four in the case of bmim + and two in the case of bdmim + are formed. The partial stability constant values for the associates of bmim + are 40, 20, 5, and 3.2 L mol -1 , of bdmim + -24 and 1.9 L mol -1 . The higher number of coordinated bmim + cations is attributed to the formation of, along with ion pairs, hydrogen bonds between 1,4 DNB DA and bmim + due to the labile hydrogen atom at position 2 of the imidazole ring, in contrast to bdmim + , which is involved only into the ion pair interactions.Key words: 1,4 dinitrobenzene dianion, 1 butyl 3 methylimidazolium cation, 1 butyl 2,3 dimethylimidazolium cation, cyclic voltammetry, ion pairs, hydrogen bond.In the last decade, ionic liquids (IL) became widely proliferated in organic electrochemistry as electrolytes due to their good electroconductivity, wide range of potentials available for measurement, incombustibility, thermal sta bility, nonvolatility, and possibility of multiple reuse. 1a One of the most wide spread varieties of IL are 1,3 dial kylimidazolium salts. Hitherto, a number of works have been published devoted to the study of electrochemical behavior in these IL of such classes of compounds tradi tional for electroorganic chemistry as mono and poly nuclear aromatic hydrocarbons, 2,3 nitro 4-7 and carbon yl 8-13 compounds, olefins, 14 alkyl and aryl halides, 9,15 amines, 16 and many others.Efficiency of the use of IL in electroorganic chemistry will be very much determined by availability of the data on their influence, including specific, on chemical behavior of the intermediate products of electrochemical processes. In particular, in the case of electroreduction in imidazole IL, an important part should be played by the reactions of radical anions (RA) and dianions (DA) formed in the course of electrochemical process with imidazolium cat ion. A number of recently published works 4,5,17,18 are de voted to the study of such reactions using RA and DA of 1,4 dinitrobenzene (1,4 DNB) as an example.It is known 18 that cyclic voltammograms (CVA curves) of 1,4 DNB in aprotic media exhibit two well resolved and completely reversible peaks corresponding to the se quential formation of its RA and DA. The CVA curves in IL 1 butyl 3 methylimidazolium tetrafluoroborate exhib it 4,5 only one completely reversible two electron peak, i.e., an inversion of the first and second electron transfer po tentials to the 1,4 DNB molecule occurs. This effect was explained by the strong ion pair interaction between 1,4 DNB DA and 1 butyl 3 methylimidazolium cation (bmim + ). However, it is known that the inversion of the first and second electron transfer potentials to the 1,4 DNB molecule can be caused not only by the forma tion of ion pairs with ...
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