Thermochemical Aspects of Partition. A Study on The Novel Hydrophobic Parameters of Multiply-Substituted Benzoic Acids.

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The thermochemical aspects of partition have been measured for multiply-substituted benzoic acids with the intention of disclosing the mode of change of the proposed novel hydrophobic parameters on multiple substitution in the phenyl ring. The substituent hydrophobic parameter (π) has been separated into two terms of enthalpic and entropic nature (πH and πS). It is necessary to take into account the effect of solvation around the hydrogen-bond-participating groups, such as OH, OCH3, and NO2, besides the benzoic CO2H in interpreting the substituent dependency of π, πH and πS. Some Hammett sigma parameters, such as σo(→OH) and σo(→OCH3), which mean the ortho substituent effect to the functional OH and OCH3 groups, respectively, act in a compensating manner to πH and πS, resulting in a vanishing effect on π. These trends are in good conformity with the enthalpy–entropy compensation rule in chemical thermodynamics.

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