Dependence of the retention of phenols upon van der waals volume, π-energy and hydrogen-bonding effects

Abstract

The retention of polyaromatic hydrocarbons (PAHs) and alkylbenzenes (PhR) can be predicted from their Van der Waals volume and π-energy effect, and that of alkyl alcohols (ROH) from their Van der Waals volume and hydrogen-bonding effect. The maximum retention is related to the Van der Waals volume, log k′ (VWV). Retention is reduced by the π-energy effect, log k′ (π), or the hydrogen-bonding effect, log k′ (HB). Therefore, the retention time is given by log k′ (PAH and PhR)  log k′ (VWV)  log k′ (π) or log k′ (ROH)  log k′ (VWV)  log k′ (HB) Furthermore, the retention of phenols (PhOH) is given by log k′ (PhOH)  log k′ (VWV)  log k′ (π)  log k′ (HB) in acidic acetonitrile—water mixtures on octadecyl-bonded silica gels.