title: A study of the vaporization enthalpies of some 1-substituted imidazoles and pyrazoles by correlation-gas chromatography.
abstract: The vaporization enthalpies of 1-methyl-, 1-ethyl-, 1-phenyl-, and 1-benzylimidazole, 1-methyl- and 1-phenylpyrazole, and trans-azobenzene are evaluated by correlation-gas chromatography (C-GC) using a variety of azines and diazines as standards. The vaporization enthalpies obtained by C-GC when compared to literature values are approximately 14 kJ·mol(-1) smaller for the imidazoles and 6 kJ·mol(-1) smaller for the pyrazoles. The literature vaporization enthalpies of 1-methylpyrrole and 1-methylindole, two closely related compounds with one less nitrogen, are reproduced by C-GC. These results suggest that the magnitude of the intermolecular interactions present in 1-substituted imidazoles and pyrazoles are significantly larger than the those present in the reference compounds and greater than or equal in magnitude to the enhanced intermolecular interactions observed previously in aromatic 1,2-diazines. The vaporization enthalpy and vapor pressure of a trans-1,2-diazine, trans-azobenzene, measured by C-GC using similar standards reproduced the literature values within experimental error.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri 63121, USA.
authors.forename: Dmitry
authors.initials: D
authors.lastname: Lipkind
authors.forename: Chatchawat
authors.initials: C
authors.lastname: Plienrasri
authors.forename: James S
authors.initials: JS
authors.lastname: Chickos
mesh_terms: D002152:Calorimetry, Differential Scanning; D002849:Chromatography, Gas; D007093:Imidazoles / Q000737:chemistry*; D044367:Phase Transition; D011720:Pyrazoles / Q000737:chemistry*; D013816:Thermodynamics; D014835:Volatilization
chemical_list: D007093:Imidazoles; D011720:Pyrazoles