Synthesis, thermal stability, and computed bond dissociation energies of tetraarylphosphonium-based mesothermal ionic liquids bearing a quinoline ring system. Issue 49 (6th December 2017)

• Record Type: Journal Article
• Authors: Soltani, Mohammad; Siu, Benjamin; Salter, E. Alan; Wierzbicki, Andrzej; West, Kevin N.; Davis, James H.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 49(2017)
• Page Start: 4628
• Page End: 4631
• Publication Date: 2017-12-06
• Subjects: Ionic liquids -- Quinoline -- Thermochemistry -- Heterocycles -- Pyrolysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.10.073
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Isomeric tetraaryphosphonium ionic liquids incorporating quinoline rings were prepared. Several of the new ionic liquids exhibited unusually high degrees of thermal stability. Thermal stability of the ILs varied by isomer. Thermal stability tracked with computed homolytic bond dissociation energies for the P–C bonds. Abstract: Seven new ionic liquids have been prepared which contain tetraarylphosphonium cations in which one of the aromatic groups is a quinoline ring. These compounds, which differ from each other in the point of attachment of the quinoline to the phosphorous core, were evaluated by DSC and TGA, then screened for thermal stability for 96 h at temperatures up to 300 °C. The observed thermal stabilities of the salts were found to be sensitive to the position of quinoline ring substitution, and correlated well with computed homolytic bond dissociation energies of the quinoline-P bonds.