The Proton Dissociation of Bio-Protic Ionic Liquids: [AAE]X Amino Acid Ionic Liquids |
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| Authors: | Ting He Cheng-Bin Hong Peng-Chong Jiao Heng Xiang Yan Zhang Hua-Qiang Cai Shuang-Long Wang Guo-Hong Tao |
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| Institution: | 1.Institute of Chemical Materials, China Academy of Engineering Physics, Mianyang 621900, China; (T.H.); (P.-C.J.); (H.X.); (Y.Z.);2.College of Chemistry, Sichuan University, Chengdu 610064, China; (C.-B.H.); (S.-L.W.) |
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| Abstract: | AAE]X composed of amino acid ester cations is a sort of typically “bio-based” protic ionic liquids (PILs). They possess potential Brønsted acidity due to the active hydrogens on their cations. The Brønsted acidity of AAE]X PILs in green solvents (water and ethanol) at room temperature was systematically studied. Various frameworks of amino acid ester cations and four anions were investigated in this work from the viewpoint of structure–property relationship. Four different ways were used to study the acidity. Acid dissociation constants (pKa) of AAE]X determined by the OIM (overlapping indicator method) were from 7.10 to 7.73 in water and from 8.54 to 9.05 in ethanol. The pKa values determined by the PTM (potential titration method) were from 7.12 to 7.82 in water. Their Hammett acidity function (H0) values (0.05 mol·L−1) were about 4.6 in water. In addition, the pKa values obtained by the DFT (proton-transfer reactions) were from 7.11 to 7.83 in water and from 8.54 to 9.34 in ethanol, respectively. The data revealed that the cationic structures of AAE]X had little effect and the anions had no effect on the acidity of AAE]X. At the same time, the OIM, PTM, Hammett method and DFT method were reliable for determining the acidic strength of AAE]X in this study. |
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| Keywords: | protic ionic liquids Brø nsted acidity amino acid ionic liquids bio-based ionic liquids |
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