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Prediction of aqueous solubility by treatment of COSMO-RS data with empirical solubility equations: the roles of global orbital cut-off and COSMO solvent radius

  • Olaide O. Wahab
  • Lukman O. Olasunkanmi
  • Krishna K. Govender
  • Penny P. GovenderEmail author
Regular Article
  • 37 Downloads

Abstract

Aqueous solubility values of (E)-2-(ethyl(4-((4-nitrophenyl)diazenyl)phenol)amino)ethanol [B1], (E)-2,2′-((4-((4-nitrophenyl)diazenyl)phenyl)azanediyl)diethanol [B2], (E)-2,2′-((3-methyl-4-((4-nitrophenyl)diazenyl)phenyl)azanediyl)diethanol [B3] and (E)-2-((4-((2,4-dinitrophenyl)diazenyl)phenyl)(ethyl)amino)ethanol [B4] were predicted by the treatment of relevant COSMO-RS data with Cramer et al. solubility equation (CSE) and general solubility equation (GSE). DMol3 computational code was employed for the study, where all calculations were carried out using VWN-BP level of theory with double numerical basis set containing polarization functions (DNP). Effects of global orbital cut-off and COSMO solvent radius (CSR) on the predicted results were examined. The results revealed that COSMO-RS data performed very well with both the CSE and GSE, but the latter exhibited a greater prediction strength on average. For nearly all the studied molecules, GSE calculated solubility (SGSE) was found to increase with orbital cut-off and reached an optimum value at a cut-off of 5.5 Å. SGSE values obtained at this and higher cut-off values studied are comparable to experimental solubility values, especially for B1, B3 and B4, while better results were obtained for B2 at lower cut-off values. CSE calculated solubility (SCSE) showed no constant trend with cut-off variation, but at cut-off values ≥ 7.0 Å the SCSE values compare well with the experimental values, especially in the cases of B2 and B3. For all the studied molecules, SGSE decreased with the increase in CSR and the most reliable CSR value for GSE was found to be 1.3 Å. On the contrary, SCSE increased with CSR and for B1 and B4, this increase was followed by a drop in predicted values at CSR > 1.3 Å. However, the best CSR value for CSE was found to be 0.5 Å for almost all the molecules. Our findings have shown that aqueous solubility (in mol/L) of azo dyes can be accurately predicted using CSE or GSE with some COSMO-RS data and that global orbital cut and COSMO solvent radius are essential parameters for accurate prediction.

Keywords

Aqueous solubility Azo dye COSMO-RS COSMO solvent radius and global orbital cut-off 

Notes

Acknowledgements

The authors express gratitude to the Department of Applied Chemistry-Centre of Nanomaterials Science Research (CNSR), Faculty of Science-University of Johannesburg (TTK14052167682) for providing financial aid, and the Centre for High Performance Computing (CHPC, South Africa) for providing the needed computational resources for this work.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflicts of interest.

Supplementary material

214_2019_2470_MOESM1_ESM.docx (41 kb)
Tables S1–S4 present the calculated solvation free energy (SFE), vapour pressure (PS), octanol–water partition coefficient (Log P) and aqueous solubility (SCSE and SGSE) at 25 °C for B1–B4, respectively. Supplementary material 1 (DOCX 40 kb)

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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Olaide O. Wahab
    • 1
    • 2
  • Lukman O. Olasunkanmi
    • 3
  • Krishna K. Govender
    • 1
    • 4
  • Penny P. Govender
    • 1
    Email author
  1. 1.Department of Applied ChemistryUniversity of JohannesburgJohannesburgSouth Africa
  2. 2.Department of Chemistry, Emmet A. Dennis College of Natural ScienceCuttington UniversitySuakokoLiberia
  3. 3.Department of Chemistry, Faculty of ScienceObafemi Awolowo UniversityIle-IfeNigeria
  4. 4.Council for Scientific and Industrial Research, National Integrated Cyber InfrastructureCentre for High Performance ComputingRosebank, Cape TownSouth Africa

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