Air stable liquid clathrates: Solid state structure and hydrocarbon solubility of organic cation triiodide salts

A series of air and water stable organic cation triiodide salts have been prepared and characterized. Almost all of the salts isolated sustain liquid clathrate phases in the presence of benzene or toluene, the compositions of which were determined via¹H NMR spectroscopy. Two of the salts were also characterized via X-ray crystallography in order to determine the nature of any solid state interionic interactions (1-ethylpyridinium triiodide, monoclinic, P2₁/c, a = 9.6031(7), b = 15.129(3), c = 8.8160(16) Å, β = 104.192(11)°, Z = 4, R = 0.041 for 2463 independent observed reflections; 1,2,4-trimethylpyridinium triiodide, orthorhombic, Pbcm, a = 9.434(4), 20.176(4), 7.411(4) Å, Z = 4, R = 0.045 for 966 observed reflections).