Conformational and Tautomeric Control by Supramolecular Approach in Ureido-N-iso-propyl,N’-4-(3-pyridin-2-one)pyrimidine
Kwiatkowski, A., Kolehmainen, E., & Ośmiałowski, B. (2019). Conformational and Tautomeric Control by Supramolecular Approach in Ureido-N-iso-propyl,N’-4-(3-pyridin-2-one)pyrimidine. Molecules, 24(13), Article 2491. https://doi.org/10.3390/molecules24132491
© 2019 by the authors.
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.
Publication in research information system
MetadataShow full item record
Additional information about fundingThis work was supported by this work was supported by the National Science Centre, Poland under Grant 2013/09/B/ST4/02308. PL-Grid Infrastructure supported this research.
Showing items with similar title or keywords.
Helttunen, Kaisa (Wiley-VCH Verlag, 2022)A calixpyrrole receptor bearing two proximally meso - meso linking isophthaloyl straps displays open and closed states depending on the calixpyrrole conformation. In the crystal structures and in non-polar solvent, ...
Theoretical and experimental studies of some main group compounds : from closed shell interactions to singlet diradicals and stable radicals Moilanen, Jani (University of Jyväskylä, 2012)Acquiring knowledge of different interactions within and between molecules is a fascinating undertaking as it not only deepens our understanding of chemical bonding but also offers insight into electronic structures, ...
Selective Formation of S4- and T-Symmetric Supramolecular Tetrahedral Cages and Helicates in Polar Media Assembled via Cooperative Action of Coordination and Hydrogen-Bonds Shi, Qixun; Zhou, Xiaohong; Yuan, Wei; Su, Xiaoshi; Neniškis, Algirdas; Wei, Xin; Taujenis, Lukas; Snarskis, Gustautas; Ward, Jas S; Rissanen, Kari; de Mendoza, Javier; Orentas, Edvinas (American Chemical Society, 2020)We report on the synthesis and self-assembly study of novel supramolecular monomers encompassing quadruple hydrogen-bonding motifs and metal coordinating 2,2’-bipyridine units. When mixed with metal ions such as Fe2+ or ...
Krupa, Justyna; Wierzejewska, Maria; Lundell, Jan (MDPI AG, 2023)Homoaggregates of isocyanic acid (HNCO) were studied using FTIR spectroscopy combined with a low-temperature matrix isolation technique and quantum chemical calculations. Computationally, the structures of the HNCO dimers ...
Kuosmanen, Riikka T.; Truong, Khai‐Nghi; Rissanen, Kari T.; Sievänen, Elina I. (Wiley-VCH Verlag, 2021)Six bile acid alkyl amide derivatives were studied with respect to their gelation properties. The derivatives were composed of three different bile acids with hexyl or cyclohexyl side chains. The gelation behaviour of all ...