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Conformational and Tautomeric Control by Supramolecular Approach in Ureido-N-iso-propyl,N’-4-(3-pyridin-2-one)pyrimidine

1
Faculty of Chemistry, Nicolaus Copernicus University in Toruń, 7 Gagarin Street, 87-100 Toruń, Poland
2
Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland
*
Author to whom correspondence should be addressed.
Academic Editor: Jennifer R Hiscock
Molecules 2019, 24(13), 2491; https://doi.org/10.3390/molecules24132491
Received: 7 June 2019 / Revised: 29 June 2019 / Accepted: 5 July 2019 / Published: 8 July 2019
(This article belongs to the Special Issue Noncovalent Interactions and Supramolecular Complex Formation)
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Abstract

Ureido-N-iso-propyl,N’-4-(3-pyridin-2-one)pyrimidine (1) and its 2-methoxy pyridine derivative (1Me) has been designed and prepared. The conformational equilibrium in urea moiety and tautomerism in the pyrimidine part have been investigated by variable temperature and 1H NMR titrations as well as DFT quantum chemical calculations. The studied compounds readily associate by triple hydrogen bonding with 2-aminonaphthyridine (A) and/or 2,6-bis(acetylamino)pyridine (B). In 1, the proton is forced to 1,3-tautomeric shift upon stimuli and keeps it position, even when one of the partners in the complex was replaced by another molecule. The observed tautomerism controlled by conformational state (kinetic trapping effect) opens new possibilities in molecular sensing that are based on the fact that reverse reaction is not preferred. View Full-Text
Keywords: tautomerism; intermolecular interactions; hydrogen bonding; molecular switch tautomerism; intermolecular interactions; hydrogen bonding; molecular switch
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kwiatkowski, A.; Kolehmainen, E.; Ośmiałowski, B. Conformational and Tautomeric Control by Supramolecular Approach in Ureido-N-iso-propyl,N’-4-(3-pyridin-2-one)pyrimidine. Molecules 2019, 24, 2491.

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