Aggregation in Aqueous Solutions of 2-(Tetrafluoro(trifluoromethyl)-λ-sulfanyl-ethan-1-ol (CFSF-ethanol)): A Comparison with Aqueous Trifluoroethanol and Hexafluoroisopropanol Using Molecular Dynamics Simulations and Dynamic Light Scattering...

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Aug 28

PMID 37636933

Authors

Samadrita Biswas

Simi Kaur

Christopher A Myers

Alan A Chen

John T Welch

Affiliations

Soon will be listed here.

Abstract

2-Tetrafluoro(trifluoromethyl)-λ-sulfanylethan-1-ol (CFSF-ethanol) combines the polar hydrophobicity of tetrafluoro(trifluoromethyl)-λ-sulfanyl (CFSF) group with the polarity of simple alcohols. The properties of aqueous solutions of the well-known fluorinated alcohols 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) were compared with those of aqueous solutions of the novel CFSF-ethanol. Those properties were computed using all atom molecular dynamics simulations with OPLS-compatible parameters. DFT ab initio calculations were used to accurately describe the nonsymmetrical, hypervalent sulfur in CFSF-ethanol. Although the molecular and conformational characteristics of CFSF-ethanol are like those of both TFE and HFIP, the greater hydrophobicity and lower polarity of CFSF-ethanol resulted in solution phase aggregation at a much lower concentration. The properties computed for TFE and HFIP in this work were consistent with published computational and experimental studies. CFSF-ethanol is predicted to be environmentally benign and hence an excellent green solvent candidate while possessing many of the same properties as TFE or HFIP.

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