scholarly journals Unexpected Intrinsic Lability of Thiol-Functionalized Carboxylate Imidazolium Ionic Liquids

Molecules ◽  
2019 ◽  
Vol 24 (19) ◽  
pp. 3571
Author(s):  
Andrea Mezzetta ◽  
Lorenzo Poderelli ◽  
Felicia D’Andrea ◽  
Christian Silvio Pomelli ◽  
Cinzia Chiappe ◽  
...  

New thiol-functionalized carboxylate ionic liquids (ILs), varying both for the cation and for the anion structures, have been prepared as new potential redox switching systems by reacting either 3-mercapto propionic acid (3-MPA) or N-acetyl-cysteine (NAC) with commercially available methyl carbonate ILs. Different ratios of thiol/disulfide ILs were obtained depending both on the acid employed in the neutralization reaction and on the reaction conditions used. Surprisingly, the imidazolium ILs displayed limited thermal stability which resulted in the formation of an imidazole 2-thione and a new sulfide ionic liquid. Conversely, the formation of the imidazole 2-thione was not observed when phosphonium disulfide ILs were heated, thus confirming the involvement of the imidazolium ring in an unexpected side reaction. An insight into the mechanism of the decomposition has been provided by means of DFT calculations.

2011 ◽  
Vol 115 (42) ◽  
pp. 12306-12314 ◽  
Author(s):  
Yang Shu ◽  
Menglin Liu ◽  
Shuai Chen ◽  
Xuwei Chen ◽  
Jianhua Wang

2013 ◽  
Vol 65 ◽  
pp. 184-190 ◽  
Author(s):  
Josefa Salgado ◽  
María Villanueva ◽  
Juan J. Parajó ◽  
Josefa Fernández

2008 ◽  
Vol 63 (1-2) ◽  
pp. 66-72 ◽  
Author(s):  
Olga B Babushkina

A series of ionic liquids consisting of 1-butyl-1-methylpyrrolidinium chloride (Pyr14Cl) and TaCl5 at molar ratios of Pyr14Cl in the range of 0.85 - 0.20 was synthesized. They exhibit potential application as electrolytes for the electrochemical deposition of tantalum. The thermal behaviour of the Pyr14Cl-TaCl5 mixtures was investigated, using differential scanning calorimetry (DSC) to estimate the range of thermal stability and to determine the optimal compositions for electrochemical trials. The Pyr14Cl-TaCl5 mixtures formed stoichiometric 3 : 2 and 2 : 3 crystalline phases with melting points of 70 °C and 130 °C, respectively, characterized by entropies of fusion of 13.6 JK−1 mol−1 and 10.1 JK−1 mol−1. The mixtures with molar fractions of Pyr14Cl equal to 0.60 and 0.40 were clear and transparent liquids and had the lowest viscosity; they were the most suitable for electrochemical applications. FTIR spectra of the Pyr14Cl-TaCl5 mixtures allowed to get insight into inter-ionic interactions and the nature of formation of these ionic liquids as a function of the molar ratio of the components.


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