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A Study of the Relative Importance of Lipophilic, π–π and Dipole–Dipole Interactions on Cyanopropyl, Phenyl and Alkyl LC Phases Bonded onto the Same Base Silica

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Abstract

Cyano (CN), butyl (C4), phenyl and octadecyl (C18) phases prepared from the same base silica gel were chromatographically characterized in order to assess the relative importance of lipophilic, π–π and dipole–dipole interactions in governing retention on these differing phases. Dipole interactions of analytes (possessing dipole moments and low lipophilicity) with CN phases were primarily responsible for the elution order. However, as the analytes’ lipophilicity increased, the lipophilic interaction predominated over the dipole interaction. In comparison, retention on the phenyl phase appeared to be complex, being controlled by a mixture of lipophilic, π–π and dipole–dipole interactions. Retention on the C4 and C18 phases was dictated by the analyte’s lipophilicity and its accessibility into the phase.

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Acknowledgments

The authors are indebted to Drs A Brooks, D. Martin, A. Ray (AstraZeneca R & D Charnwood, Loughborough, UK) and Mr N. Riasat (University of Nottingham, Department of Pharmaceutical Sciences, Nottingham, UK) for assisting in the elucidation of the degradative stability of cyano phases at intermediate pH.

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Authors and Affiliations

  1. Laboratory of Pharmaceutical Analysis, School of Pharmacy, Aristotelian University, 54124, Thessaloniki, Greece

    Catherine Markopoulou

  2. Strathclyde Institute for Pharmacy and Biomedical Sciences, 27, Taylor Street, Glasgow, G4 0NR, Scotland, UK

    Tracey Tweedlie, David Watson, Graham Skellern & Houssam Reda

  3. AstraZeneca R&D Lund, 221 87, Lund, Sweden

    Patrik Petersson

  4. Hichrom Ltd, 1 Markham Centre, Station Road, Theale, Reading, Berkshire, RG7 4PE, UK

    Hannah Bradstock & Melvin Euerby

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  1. Catherine Markopoulou
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  2. Tracey Tweedlie
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  3. David Watson
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  4. Graham Skellern
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  5. Houssam Reda
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  6. Patrik Petersson
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  7. Hannah Bradstock
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  8. Melvin Euerby
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Correspondence to Melvin Euerby.

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Markopoulou, C., Tweedlie, T., Watson, D. et al. A Study of the Relative Importance of Lipophilic, π–π and Dipole–Dipole Interactions on Cyanopropyl, Phenyl and Alkyl LC Phases Bonded onto the Same Base Silica. Chroma 70, 705–715 (2009). https://doi.org/10.1365/s10337-009-1224-7

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  • DOI: https://doi.org/10.1365/s10337-009-1224-7

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