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Novel keto–enol tautomerism in 1,3,5-trihydroxybenzene systems

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Abstract

We report a new synthesis of the water-soluble compound 1,3,5-trihydroxy-2,4,6-trimethylsulfonic acid (1), which exists in two tautomeric forms (60 : 40::enol%:keto%) and can be used as a proton conductor. Quantum chemical calculations show the importance of intramolecular hydrogen bonding and the presence of implicit MeOH solvent on the relative stabilities of the tautomers. 1 complexes with lanthanides through its sulfonato groups and forms a layered cage-like structure with one intramolecular and two intermolecular hydrogen bonds.

Graphical abstract: Novel keto–enol tautomerism in 1,3,5-trihydroxybenzene systems

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Article information


Submitted
21 May 2020
Accepted
24 Aug 2020
First published
26 Sep 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Novel keto–enol tautomerism in 1,3,5-trihydroxybenzene systems

M. Ruaysap, S. R. Kennedy, C. M. Mayhan, S. P. Kelley, H. Kumari, C. A. Deakyne and J. L. Atwood, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC03639K

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