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Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates

  • PHYSICAL CHEMISTRY OF SEPARATION PROCESSES. CHROMATOGRAPHY
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Abstract

Recurrent approximation of retention times in reversed-phase high performance liquid chromatography (RP-HPLC), tR(C + ΔC) = atR(C) + b, where C is the acetonitrile concentration in the eluent, and ΔC is the constant “step” of its variation, for six specially synthesized N-substituted p-toluenesulfonamides confirmed the presence of anomalies previously revealed for some complex polyfunctional organic compounds. The reason for these anomalies is the presence of sulfonamide –SO2–NH fragments in the molecules, which leads to hydration of sorbates in aqueous solutions, or, more precisely, to a change in the ratio of their non-hydrated and hydrated forms because of a shift in the equilibrium Х + Н2О \( \rightleftarrows \) Х·Н2О (*) as a result of a change in the eluent composition. The same effect is indicated by the strong antibatic dependence of the retention indices RI(C) of all sulfonamides under study; the coefficients dRI/dC vary from –1.9 to –4.0, these values being much higher in magnitude than for compounds that do not form hydrates. Further independent evidence in favor of the transformation of sorbates due to variation of the eluent composition is the dependence of the relative absorbance Arel = A(254)/A(220) on the acetonitrile content in the eluent. This suggests changes in the chemical nature of chromophores in sulfonamide molecules depending on the equilibrium state (*).

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Notes

  1. For retention indices, IUPAC recommends the one-letter symbol “I.” However, it has other meanings (electric current, radiation intensity, peak intensity in mass spectra, etc.); as a result, expressions containing “I” symbols with different meanings can appear in chromatography. Therefore, we prefer the two-letter symbol RI.

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Authors and Affiliations

  1. Institute of Chemistry, St. Petersburg State University, 198504, St. Petersburg, Russia

    I. G. Zenkevich, D. A. Nikitina & T. A. Kornilova

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  1. I. G. Zenkevich
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  2. D. A. Nikitina
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  3. T. A. Kornilova
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Correspondence to I. G. Zenkevich.

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Translated by L. Smolina

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Zenkevich, I.G., Nikitina, D.A. & Kornilova, T.A. Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates. Russ. J. Phys. Chem. 95, 1931–1941 (2021). https://doi.org/10.1134/S0036024421090326

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