Dicarboxylic Acid Separation by Dynamic and Size-Matched Recognition in Solution and in the Solid State

Vijith Kumar; Tullio Pilati; Giancarlo Terraneo; Gianluca Ciancaleoni; Alceo Macchioni; Giuseppe Resnati; Pierangelo Metrangolo

doi:10.1002/anie.201711822

Dicarboxylic Acid Separation by Dynamic and Size-Matched Recognition in Solution and in the Solid State

Angew Chem Int Ed Engl. 2018 Jan 26;57(5):1327-1331. doi: 10.1002/anie.201711822. Epub 2018 Jan 2.

Authors

Vijith Kumar¹, Tullio Pilati¹, Giancarlo Terraneo¹, Gianluca Ciancaleoni², Alceo Macchioni³, Giuseppe Resnati¹, Pierangelo Metrangolo¹

Affiliations

¹ DCMIC "Giulio Natta", Politecnico di Milano, Via L. Mancinelli 7, 20131, Milano, Italy.
² Dip. Chimica e Chimica Industriale, Università degli Studi di Pisa, Via Giuseppe Moruzzi 13, 56124, Pisa, Italy.
³ Dipartimento di Chimica, Biologia e Biotecnologie and CIRCC, Università degli Studi, Via Elce di Sotto 8, 06123, Perugia, Italy.

PMID: 29226498
DOI: 10.1002/anie.201711822

Abstract

Bis(trimethylammonium) alkane diiodides dynamically encapsulate dicarboxylic acids through intermolecular hydrogen bonds between the I^- anions of the hosts and the carboxylic OH groups of the guests. A selective recognition is realized when the size of the I^- ⋅⋅⋅HOOC(CH₂ /CF₂ )_n COOH⋅⋅⋅I^- superanion matches the dication alkyl chain length. Dynamic recognition is also demonstrated in solution, where the presence of the size-matching organic salt boosts the acid solubility profile, thus allowing efficient mixture separation.

Keywords: co-crystals; dicarboxylic acids; halogen bonds; hydrogen bonds; separation.

Publication types

Research Support, Non-U.S. Gov't