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Equilibrium Acidities of Nitroalkanes in an Ionic Liquid
Feixiang Gao1, Pengju Ji1, Jin-Pei Cheng1,2
1Center of Basic Molecular Science (CBMS), Department of Chemistry , Tsinghua University , Beijing 100084 , China.
Abstract:
The acidity ladder scale in [BMPY][NTf2] was successfully expanded toward the weak acidity region for about five more p K units compared to the previously established one. This allows the acidities of a series of 13 aliphatic and aromatic nitroalkanes to be determined accurately by the UV-vis spectroscopic method. The acidity of nitroalkane in [BMPY][NTf2] covers ∼8 p K units and is significantly weaker than those in DMSO and water. The Hammett plot for 4-substituted phenylnitromethanes shows an excellent linearity with a slope of 2.06, which is rather close to that in DMSO but significantly larger than that in water (0.80). The regression analyses reveal that the solvation behavior of [BMPY][NTf2] on the acidic dissociations of C-H acids is similar to that of DMSO.
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