Author(s)

Pavel Straka, Petr Buryan

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Institute of Rock Structure and Mechanics, Academy of Sciences of the Czech Republic, Prague, Czech Republic..

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.

Alkyl Phenols, Alkyl Benzenes, Retention Times, Molecular Mechanics, Van der Waals Forces

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.