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A Systematic Theoretical Study on the Acidities for Cations of Ionic Liquids in Dimethyl Sulfoxide
Zhen Wang1,2, Yongjun Zheng1, Yong Zheng1
1School of Chemical and Environmental Engineering , Anyang Institute of Technology , Anyang 455000 , China.
Abstract:
The acidities of 40 commonly seen cations of ionic liquids (CILs) in dimethyl sulfoxide (DMSO) were investigated by a well-established theoretical method, SMD/M06-2X/6-311++G (2df,2p)//B3LYP/6-31+G(d). The calculated p Ka's agree excellently with the available experimental data and range from 20.0 to 45.8 with an acidity order of 1,3-dialkylimidazolium > amidinium > pyridinium > tetraalkylphosphonium > morpholinium > pyrrolidinium ≈ piperidinium > guanadinim cations. The established acidity scale in this work provides a useful tool, as verified by the acidity comparisons, to assess the stability of ILs under various extent basic conditions, and also reveals the relative basicity of several classical N-heterocyclic carbenes and olefins as well as ylides.
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