Effect of fluorination on the partitioning of alcohols. (17th December 2019)

• Record Type: Journal Article
• Authors: Soroush Barhaghi, Mohammad; Luyet, Chloe; Potoff, Jeffrey J.
• Is Part Of: Molecular physics. Volume 117:Number 23/24(2019)
• Page Start: 3827
• Page End: 3839
• Publication Date: 2019-12-17
• Subjects: Fluorotelomers -- free energy -- Monte Carlo -- TraPPE; Molecules -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Molécules -- Périodiques; Chimie physique et théorique -- Périodiques; 539.6.05
• DOI: 10.1080/00268976.2019.1669837
• Languages: English
• ISSNs: 0026-8976

Abstract

ABSTRACT: In order to understand the role of fluorination on the interactions and partitioning of alcohols in aqueous and organic environments, isobaric-isothermal ensemble Monte Carlo simulations are used to determine environmental predictors, such as free energies of hydration and solvation in 1-octanol and n-hexadecane. Calculations are performed with the united-atom Transferable Potentials for Phase Equilibria (TraPPE) force field and compared against available experimental data. TraPPE was found to provide reliable qualitative predictions of trends with respect to the effect of fluorination on partitioning. Investigation of the local solvation environment around the hydroxyl group reveals that fluorination of carbons closest to the hydroxyl group has the greatest effect on solvation free energies for alcohols in water, 1-octanol and n-hexadecane. GRAPHICAL ABSTRACT: