A1 Journal article (refereed)
Conformational and Tautomeric Control by Supramolecular Approach in Ureido-N-iso-propyl,N’-4-(3-pyridin-2-one)pyrimidine (2019)

Kwiatkowski, Adam; Kolehmainen, Erkki; Ośmiałowski, Borys (2019) Conformational and Tautomeric Control by Supramolecular Approach in Ureido-N-iso-propyl,N’-4-(3-pyridin-2-one)pyrimidine. Molecules, 24 (13), 2491. DOI: 10.3390/molecules24132491

JYU authors or editors

Publication details

All authors or editors: Kwiatkowski, Adam; Kolehmainen, Erkki; Ośmiałowski, Borys

Journal or series: Molecules

eISSN: 1420-3049

Publication year: 2019

Volume: 24

Issue number: 13

Article number: 2491

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/molecules24132491

Open Access: Publication published in an open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/65116

Additional information: This article belongs to the Special Issue Noncovalent Interactions and Supramolecular Complex Formation.

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.

Free keywords: tautomerism; intermolecular interactions; hydrogen bonding; molecular switch

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2019

JUFO rating: 1