Vaporization enthalpies of the α,ω-alkanediols by correlation gas chromatography

Journal of Chemical and Engineering Data

Volumn 51, Issue 6, 2006, Pages 2246-2254

  Umnahanant, Pataporn ^a   Kweskin, Shasha ^a   Nichols, Gary ^a   Dunn, Matthew J ^a   Smart Ebinne, Hareta ^a   Chickos, James S ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CORRELATION GAS CHROMATOGRAPHY; INTRAMOLECULAR BONDING; VAPORIZATION ENTHALPIES;

ENTHALPY; GAS CHROMATOGRAPHY; HYDROGEN BONDS; SOLUTIONS; SUBLIMATION;

ALCOHOLS;

EID: 33751361781     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je060333x     Document Type: Article

References (30)

1. Pouchert, C. J. The Aldrich Libray of FT-IR Spectra, Vapor Phase, Vol. 3; Aldrich Chemical Co.: Milwaukee, WI, 1989.
2. Klein, R. A. Ab initio conformational studies on diols and binary diol-water systems using DFT methods. Intramolecular hydrogen bonding and 1:1 complex formation with water. J. Comput. Chem. 2002, 23, 585.
3. Klein, R. A. Hydrogen bonding in diols and binary diol-water systems investigated using DFT methods. II. Calculated infrared OH-stretch frequencies, force constants, and NMR chemical shifts correlate with hydrogen bond geometry and electron density topology. A reevaluation of geometrical criteria for hydrogen bonding. J. Comput. Chem. 2003, 24, 1120-31.
4. Klein, R. A. Electron density topological analysis of hydrogen bonding in glucopyranose and hydrated glucopyranose. J. Am. Chem. Soc. 2002, 124, 13931-7.
5. 16. J. Chem. Thermodyn. 2005, 37, 941-53.
6. Davies, M.; Thomas, G. H. The lattice energies, infra-red spectra, and possible cyclization of some dicarboxylic acids. Trans. Faraday Soc. 1960, 56, 185-92.
7. Chickos, J. S.; Hesse, D. G.; Liebman, J. F. Heat capacity corrections to a standard state: a comparison of new and some literature methods for organic liquids and solids. Struct. Chem. 1993, 4, 271-8.
8. Chickos, J. S.; Hosseni, S.; Hesse, D. G.; Liebman, J. F. A group additivity approach for the estimation of heat capacities of organic liquids and solids at 298 K. Struct. Chem. 1993, 4, 261-9.
9. Gardner, P. J.; Hussain, K. S. The standard enthalpies of formation of some aliphatic diols. J. Chem. Thermodyn. 1972, 4, 819-27.
10. Schierholtz, O. J.; Staples, M. L. Vapor pressures of certain glycols. J. Am. Chem. Soc. 1935, 57, 2709-11.
11. Gallaugher, A. F.; Hibbert, H. Studies on reactions relating to carbohydrates and polysaccharides. LV. Vapor pressures of the polyethylene glycols and their derivatives. J. Am. Chem. Soc. 1937, 59, 2521-5.
12. Stull, D. R. Vapor pressure of pure substances. Organic compounds. Ind. Eng. Chem. 1947, 39, 517-50.
13. Al-Najjar, H.; Al-Sammerrai, D. Thermogravimetric determination of the heat of vaporization of some highly polar solvents. J. Chem. Technol. Biotechnol. 1987, 37, 145-52.
14. Jones, W. S.; Tamplin, W. S. Glycols; American Chemical Society Monograph Series 114; American Chemical Society: Washington, DC, 1952.
15. Knauth, P.; Sabbah, R. Energetics of intra- and intermolecular bonds in ω-alkanediols. II. Thermochemical study of 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, and 1,5-pentanediol. Struct. Chem. 1990, 1, 43-6.
16. Eusebio, M. E.; Lopes Jesus, A. J.; Cruz, M. S. C.; Leitao, M. L. P.; Redinha, J. S. Enthalpy of vaporization of butanediol isomers. J. Chem. Thermodyn. 2003, 35, 123-9.
17. Knauth, P.; Sabbah, R. Energetics of intra and intermolecular bonds in ω-alkanediols. in. Thermochemical study of 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, and 1,10-decanediol at 298.15 K. Can. J. Chem. 1990, 68, 731-4.
18. Piacente, V.; Ferro, D.; Della Gatta, G. Vaporization enthalpies of a series of αω-alkanediols from vapour pressure measurements. Thermochim. Acta. 1993, 223, 65-73.
19. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K. Thermodynamic properties and ideal-gas enthalpies of formation for butyl vinyl ether, 1,2-dimethoxyethane, methyl glycolate, bicyclo-[2.2.1]hept-2-ene, 5-vinylbicyclo[2.2.1]hept-2-ene, trans-azobenzene, butyl acrylate, di-tert-butyl ether, and hexane-1,6-diol. J. Chem. Eng. Data. 1996, 41, 1285-302.
20. Piacente, V.; Ferro, D.; Della Gatta, G. Vaporization enthalpies of five odd-numbered (C7-C15) α,ω-alkanediols from vapour pressure measurements. Thermochim. Acta 1994, 232, 317-21.
21. Steele, W. V.; Chirico, R. D.; Hossenlopp, I. A.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K. Determination of ideal-gas phase enthalpies of formation for key compounds. In Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties; Cunningham, J. R., Jones, D. K., Eds.; AICHE: New York, 1994; pp 188-215.
22. Nichols, G.; Kweskin, S.; Frericks, M.; Reiter, S.; Wang, G.; Orf, J.; Carvallo, B.; Hillesheim-Cox, D.; Chickos, J. S. An evaluation of the vaporization, fusion and sublimation enthalpies of the 1-alkanols. The vaporization enthalpy of 1-, 6-, 7-, and 9-heptadecanol, 1 -octadecanol,1- eicosanol, 1-docosanol, 1-hexacosanol and cholesterol at T= 298.15 K by correlation-gas chromatography. J. Chem. Eng. Data 2006, 57, 475-82.
23. 29 by correlation-gas chromatography. Thermochim. Acta 2004, 424, 111-21.
24. 38 at T= 298.15 by correlation gas chromatography. J. Chem. Eng. Data 2004, 49, 620-30.
25. 30 at T = 298.15 by correlation gas chromatography. J. Chem. Eng. Data 2004, 49, 77-85.
26. Stephenson, R. M.; Malanowski, S. Handbook of the Thermodynamics of Organic Compounds; Elsevier: New York, 1987.
27. 2n+2: Normal alkanes with 36 ≥ n and isomers for n = 4 through n = 9. J. Chem. Ref. Data 2000, 29, 1-39.
28. Chickos, J. S.; Acree, W., Jr.; Liebman, W. J. F. Estimating phase change entropies and enthalpies. In Computational Thermochemistry, Prediction and Estimation of Molecular Thermodynamics; Frurip, D., Irikura, K., Eds.; ACS Symposium Series 677; American Chemical Society: Washington, DC, 1998; pp 63-93.
29. For a discussion and summary of the literature, see Velez, E.; Quijano, J.; Gaviria, J.; Roux, M. V.; Jimenez, P.; Temprado, M.; Martin-Valcarcel, G.; Perez-Parajon, J.; Notario, R. Calorimetric and computational study of 3-buten-1-ol and 3-butyn-1-ol. Estimation of the enthalpies of formation of the 1-alkenols and 1-alkynols. J. Phys. Chem. A 2005, 109, 7832-8.
30. 24. Bull. Chem. Soc. Jpn. 1999, 72, 943-6.