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Crystallization of organic salts from the gas phase: When does proton transfer take place?

O’Malley, Ciarán
; 
Erxleben, Andrea
; 
McArdle, Patrick
; 
Simmie, John M.
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Publication Date
2020-12-13
Keywords
Salts, Reaction mechanisms, Crystal structure, Sublimation, organic salt, proton transfer, density functional calculations, diflunisal
Type
Article
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Citation
O’Malley, Ciarán, Erxleben, Andrea, McArdle, Patrick, & Simmie, John M. (2020). Crystallization of Organic Salts from the Gas Phase: When Does Proton Transfer Take Place? Crystal Growth & Design. doi:10.1021/acs.cgd.0c01248
Abstract
Salt formation with proton transfer is observed in crystals grown by cosublimation of the salt coformers. Diflunisal salts were obtained with 4-[3-(pyridin-4-yl)propyl]pyridine, piperazine, and 4-dimethylaminopyridine. Modeling studies indicate that proton transfer does not take place for an acid–base H-bonded adduct in the gas phase. However, modeling larger molecular clusters shows that proton transfer can take place spontaneously within a molecular cluster in the absence of a solvent.
Funder
Science Foundation Ireland
European Regional Development Fund
Publisher
American Chemical Society
Publisher DOI
10.1021/acs.cgd.0c01248
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Collections
School of Biological and Chemical Sciences (Scholarly Articles)