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Retention of Halogenated Solutes on Stationary Phases Containing Heavy Atoms
College of Bioscience and Biotechnology, Chubu University, 1200 Matsumotocho, Kasugai-shi, Aichi 487-8501, Japan
Nippon Filcon Co., Ltd., 2220 Ohmaru, Inagi-shi, Tokyo 206-8577, Japan
* Author to whom correspondence should be addressed.
Received: 18 January 2013; in revised form: 29 April 2013 / Accepted: 2 May 2013 / Published: 6 May 2013
Abstract: To examine the effects of weak intermolecular interactions on solid-phase extraction (SPE) and chromatographic separation, we synthesized some novel stationary phases with a heavy atom effect layer by immobilizing halogenated aromatic rings and hydroxyl groups onto the surface of a hydrophilic base polymer. Using SPE cartridges packed with the functionalized materials, we found that the heavy atom stationary phases could selectively retain halophenols in organic solvents, such as 1-propanol which blocks the hydrogen bonding, or acetonitrile which blocks the p-p interaction. The extraction efficiency of the materials toward the halophenols depended on the dipole moments of phenoxy groups present as functional groups. On the other hand, the extraction efficiency of solutes toward the functional group depended on their molar refractions, i.e., induced dipole moments. The retention of the solutes to the stationary phase ultimately depended on not only strong intermolecular interactions, but also the effects of weak interactions such as the dispersion force.
Keywords: solid-phase extraction; heavy atom effect; halophenoxy functional groups; induced dipole moment
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Miwa, T.; Yamamoto, A.; Saito, M.; Inoue, Y. Retention of Halogenated Solutes on Stationary Phases Containing Heavy Atoms. Molecules 2013, 18, 5163-5171.
Miwa T, Yamamoto A, Saito M, Inoue Y. Retention of Halogenated Solutes on Stationary Phases Containing Heavy Atoms. Molecules. 2013; 18(5):5163-5171.
Miwa, Toshio; Yamamoto, Atsushi; Saito, Mitsuru; Inoue, Yoshinori. 2013. "Retention of Halogenated Solutes on Stationary Phases Containing Heavy Atoms." Molecules 18, no. 5: 5163-5171.