The DOI matches its Crossref record; 48 of the 48 references it cites were found in a registry or an index.
Molecular origins of fluorocarbon hydrophobicity
Abstract
We have undertaken atomistic molecular simulations to systematically determine the structural contributions to the hydrophobicity of fluorinated solutes and surfaces compared to the corresponding hydrocarbon, yielding a unified explanation for these phenomena. We have transformed a short chain alkane, n-octane, to n-perfluorooctane in stages. The free-energy changes and the entropic components calculated for each transformation stage yield considerable insight into the relevant physics. To evaluate the effect of a surface, we have also conducted contact-angle simulations of water on self-assembled monolayers of hydrocarbon and fluorocarbon thiols. Our results, which are consistent with experimental observations, indicate that the hydrophobicity of the fluorocarbon, whether the interaction with water is as solute or as surface, is due to its “fatness.” In solution, the extra work of cavity formation to accommodate a fluorocarbon, compared to a hydrocarbon, is not offset by enhanced energetic interactions with water. The enhanced hydrophobicity of fluorinated surfaces arises because fluorocarbons pack less densely on surfaces leading to poorer van der Waals interactions with water. We find that interaction of water with a hydrophobic solute/surface is primarily a function of van der Waals interactions and is substantially independent of electrostatic interactions. This independence is primarily due to the strong tendency of water at room temperature to maintain its hydrogen bonding network structure at an interface lacking hydrophilic sites.
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“Perfluorocarbons have very low water solubility (Dalvi and Rossky, 2010).”
From Nothing lasts forever: understanding microbial biodegradation of polyfluorinated compounds and perfluorinated alkyl substances (2022) · cites this paper as Dalvi and Rossky, 2010
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Cited by
Wackett, L. P. (2022) · Microbial Biotechnology · doi:10.1111/1751-7915.13928 · Cited by 165
Giovambattista, N., Rossky, P. J., & Debenedetti, P. G. (2012) · Annual Review of Physical Chemistry · doi:10.1146/annurev-physchem-032811-112007 · Cited by 149
Self-citationJackson, T. W., Scheibly, C. M., Polera, M. E., & Belcher, S. M. (2021) · Environmental Science & Technology · doi:10.1021/acs.est.1c01200 · Cited by 87
Krieg, E., Weissman, H., Shimoni, E., Bar On (Ustinov), A., & Rybtchinski, B. (2014) · Journal of the American Chemical Society · doi:10.1021/ja503906p · Cited by 79
Accioni, F., García-Gómez, D., & Rubio, S. (2021) · Journal of Chromatography A · doi:10.1016/j.chroma.2020.461777 · Cited by 14
Metadata
- Authors
- Dalvi, V. H., & Rossky, P. J.
- Affiliations
- Departments of Chemical Engineering and
- Venue
- Proceedings of the National Academy of Sciences
- Publisher
- National Academy of Sciences
- Published
- 2010-07-19
- Volume
- 107
- Issue
- 31
- Pages
- 13603-13607
- ISSN
- 0027-8424
- 1091-6490
- Cited by
- 421
- References
- 48
- Language
- en
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