A Study of the Behavior of Alkyl Side Chains Phenols and Arenes in Polar and Nonpolar GC Stationary Phases

DOI: 10.4236/ajac.2011.23040   PDF   HTML     4,792 Downloads   7,782 Views   Citations

Abstract

Gas chromatographic measurements of the relative retention times of alkyl-substituted arenes and phenols on capillary columns at temperatures of 125 – 140°C have shown that logarithms of retention times increase bilinearly with the number of carbon atoms in the molecule. It was found that in a high density stationary phase, the longer alkyl side chains of compounds in question are subject to cyclization as a result of the resistance force of this phase affecting molecules during their thermal and diffusion motion. Consequently, common conventional aromatic-aliphatic molecules become new molecules with quasi-alicyclic rings. In comparison with the conventionally conceived molecules, the resulting aromatic–quasi-alicyclic molecules are characterized by rather different, possibly even completely different non-covalent interactions between the molecules, which then affect the retention characteristics. Moreover, cyclization facilitates the mixing of n-alkyl arenes and n-alkyl phenols with high-molecular stationary phases, because the thermodynamic condition for mixing is better fulfilled.

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P. Straka and P. Buryan, "A Study of the Behavior of Alkyl Side Chains Phenols and Arenes in Polar and Nonpolar GC Stationary Phases," American Journal of Analytical Chemistry, Vol. 2 No. 3, 2011, pp. 324-331. doi: 10.4236/ajac.2011.23040.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] P. Buryan and J. Macák, “Partial Explanation of the Anomaly in the Relationship between the Logarithm of Retention and the Carbon Number of Monohydric Phenols,” Journal of Chromatography A, Vol. 237, No. 3, 1982, pp. 381-388. doi:10.1016/S0021-9673(00)97624-6
[2] H. Purnell, “Gas Chromatography,” John Wiley and Sons Inc., New York, 1962.
[3] E. Leibnitz and H. G. Struppe, “Handbuch der Gas-Chromatographie,” AVG & Portik K.-G., Lepzig, 1966.
[4] G. Guiochon, “Retention Indices in Programmed Temperature Gas Chromatography,” Analytical Chemistry, Vol. 36, No. 3, 1964, pp. 661-663. doi:10.1021/ac60209a034
[5] W. E. Hartus and H. W. Habgood, “Programmed Temperature Gas Chromatography,” John Wiley and Sons Inc., New York, 1966.
[6] C. Simpson, “Gas Chromatography,” Kogan Page, London, 1970.
[7] P. Straka, P. Buryan and J. Nahunkova, “Possibilities of Cyclization of Side Alkyl Chains of n-Alkyl Phenols and n-Alkyl Benzenes in the Environment of a Stationary Phase,” Acta Geodynamica et Geomaterialia, Vol. 5, No. 1 (149), 2008, pp. 65-76.
[8] P. Straka, “Chemical structure of coal substance,” Acta Montana Series AB, No. 12(132), 2003, pp. 7-47.
[9] G. A. Carlson, “Computer Studies of Coal Molecular Structure”, Proceedings 1991 International Conference on Coal Science, Newcastle upon Tyne, September 1991, pp. 24-27.
[10] A. C. T. van Duin and J. S. S. Damsté, “Computational Chemical Investigation into Isorenieratene Cyclisation,” Organic Geochemistry, Vol. 34, No. 4, 2003, pp. 515- 526. doi:10.1016/S0146-6380(02)00247-4
[11] A. Howard, J. McIver and J. Collins, “HyperChem Computational Chemistry,” Publishing HC40-00-03-00, Hypercube Inc., Waterloo/Ontario/Canada, 1994.
[12] U. Becker and N. L. Allinger, “Molecular Mechanics,” American Chemical Society, Monograph 177, Washington D. C., 1982.
[13] N. L. Allinger and Y. H. Yuh, “Quantum Chemistry Program Exchange,” Indiana University, Bloomington, 1982.
[14] Collective of authors, “Spravotschnik Chimika, Osnovnyje Svojstva Neorganitcheskich I Organitcheskich Sojedinenij,” Gosudarstvennoe Nautschno-Technitscheskoe Izdatelstvo Chimitscheskoj Literatury, Moskva, 1951.
[15] M. Vecera, J. Gasparic, J. Churacek and J. Borecky, “Chemical Tables of Organic Compounds,” SNTL-Technical Literature Publishing House, Praha, 1975.
[16] J. H. Hildebrand and R. L. Scott, “Solubility of Non-Electolytes,” Reinhold publishing company, New York, 1959.
[17] J. Brandrup and E. H. Immergut, “Polymer Handbook,” John Wiley and Sons Inc., New York, 1975.
[18] J. Mleziva, “Polymery,” Sobotales Publishing industry, Praha, 1993, p. 467.
[19] M. Naczk and F. Shahidi, “Extraction and Analysis of Phenolics in Food,” Journal of Chromatography A, Vol. 1054, No. 1-2, 2004, pp. 95-111.
[20] P. Hobza, R. Zahradnik, K. Müller-Dethlefs, “The World of Non-Covalent Interactions: 2006,” Collection Czechoslovak Chemical Communications, Vol. 71, No. 4, 2006, pp. 443-531. doi:10.1135/cccc20060443

  
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