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A new method to define the hydrophilic-lipophilic balance

A. BETERINGHE1,* , A. C. RADUTIU1, A. MISCHIE1, F. SPAFIU1

Affiliation

  1. Institute of Physical Chemistry "Ilie Murgulescu" of the Romanian Academy , Laboratory of Coordination and Supramolecular Chemistry, Splaiul Independentei 202, Bucharest, 060021, Romania

Abstract

Experimental values of the molecular hydrophobicity (RM0) determined by reverse-phase thin-layer chromatography (RPTLC) for four isomeric pairs of bis-dinitrophenyl-Kryptofix-22 derivatives (1a, 1b; 1c, 1d; 1e, 1f; and 1g, 1h) were correlated (R2 > 0.970) by means of values of the hydrophilic-lipophilic balance (HLB) calculated by a new method involving several physico-chemical characteristics: the Ghose-Crippen octanol-water partition coefficient (AlogP), Molecular Surface Area (MSA), energy of dispersion forces between molecules (D), energy of dipolar intermolecular forces between molecules (P), hydrophobic surface area (HySA), surface area (SA) and a statistical factor (SFf(ST)) which depends on the surface tension. The same strategy involving HLB values was applied for 50 alcohols, 37 amines and 15 ethers, this time involving comparisons with experimental logP values; good correlations were obtained for alcohols (R2 = 0.855), amines (R2 = 0.922) and ethers (R2 = 0.901)..

Keywords

Molecular hidrophobicity RM0, Hydrophilic-lipophilic balance, logP, QSPR, Alcohols, Amines, Ethers.

Submitted at: March 16, 2015
Accepted at: May 7, 2015

Citation

A. BETERINGHE, A. C. RADUTIU, A. MISCHIE, F. SPAFIU, A new method to define the hydrophilic-lipophilic balance, Journal of Optoelectronics and Advanced Materials Vol. 17, Iss. 5-6, pp. 846-855 (2015)