Basic ionic liquids based on monoquaternized 1,4-diazobicyclo[2.2.2]octane (dabco) and dicyanamide anion: Physicochemical and solvent properties

Chiappe, Cinzia; Melai, Bernardo; Sanzone, Angelo; Valentini, Giulia

doi:10.1351/PAC-CON-08-11-01

Pure Appl. Chem., 2009, Vol. 81, No. 11, pp. 2035-2043

http://dx.doi.org/10.1351/PAC-CON-08-11-01

Published online 2009-10-30

Basic ionic liquids based on monoquaternized 1,4-diazobicyclo[2.2.2]octane (dabco) and dicyanamide anion: Physicochemical and solvent properties

Cinzia Chiappe*, Bernardo Melai, Angelo Sanzone and Giulia Valentini

Department of Chemistry and Industrial Chemistry, University of Pisa, Via Risorgimento 35, 56126 Pisa, Italy

Abstract: In this paper, we report on the synthesis and application of monosubstituted diazabicyclo[2.2.2]octane (dabco) cations associated with a basic anion, dicyanamide. Key properties of these salts—phase transitions, density, and conductivity—were measured and compared to those of other common ionic liquids (ILs). Moreover, solvatochromic dyes were used to assess their solvation properties. The Heck cross-coupling reaction was evaluated in dabco-based ILs and compared with the behavior in common unfunctionalized ILs, evidencing good catalyst stability and a high recyclability in these basic ILs.