Boiling points of halogenated ethanes: an explanatory model implicating weak intermolecular hydrogen-halogen bonding |
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Authors: | Beauchamp Guy |
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Institution: | Department of Chemistry, Cégep de l'Outaouais College, 333 Cité des Jeunes, Gatineau, Québec, Canada J8Z 6M4. gbeauchamp@cegepoutaouais.qc.ca |
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Abstract: | This study explores via structural clues the influence of weak intermolecular hydrogen-halogen bonds on the boiling point of halogenated ethanes. The plot of boiling points of 86 halogenated ethanes versus the molar refraction (linked to polarizability) reveals a series of straight lines, each corresponding to one of nine possible arrangements of hydrogen and halogen atoms on the two-carbon skeleton. A multiple linear regression model of the boiling points could be designed based on molar refraction and subgroup structure as independent variables (R(2) = 0.995, standard error of boiling point 4.2 degrees C). The model is discussed in view of the fact that molar refraction can account for approximately 83.0% of the observed variation in boiling point, while 16.5% could be ascribed to weak C-X...H-C intermolecular interactions. The difference in the observed boiling point of molecules having similar molar refraction values but differing in hydrogen-halogen intermolecular bonds can reach as much as 90 degrees C. |
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