Next Article in Journal
Mechanism of Albuminuria Reduction by Chymase Inhibition in Diabetic Mice
Next Article in Special Issue
Ensemble-Based Analysis of the Dynamic Allostery in the PSD-95 PDZ3 Domain in Relation to the General Variability of PDZ Structures
Previous Article in Journal
Comparative Study of the Steroidogenic Effects of Human Chorionic Gonadotropin and Thieno[2,3-D]pyrimidine-Based Allosteric Agonist of Luteinizing Hormone Receptor in Young Adult, Aging and Diabetic Male Rats
Previous Article in Special Issue
Intramolecular Hydrogen Bond Driven Conformational Selectivity of Coumarin Derivatives of Resorcin[4]arene
Article

Enaminone Substituted Resorcin[4]arene—Sealing of an Upper-Rim with a Directional System of Hydrogen-Bonds

1
Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 60-614 Poznań, Poland
2
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
3
Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, Poland
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(20), 7494; https://doi.org/10.3390/ijms21207494
Received: 15 September 2020 / Revised: 8 October 2020 / Accepted: 9 October 2020 / Published: 11 October 2020
(This article belongs to the Special Issue Structure, Energy, and Dynamics of Molecular Interactions)
The paper presents the synthesis of an enaminone resorcin[4]arene via a thermally activated o-quinomethide. The crystal structure indicates that in the solid state all enaminone units participate in a unidirectional seam of 12 intramolecular hydrogen bonds that are formed around the cavity. The molecule exhibits C2 symmetry, with two opposite-laying enaminone units directed inside the cavity (“in”), and the other two units outside the cavity (“out”). In the solution the enaminone resorcin[4]arene exists as a mixture of conformers with distribution controlled by temperature and solvent. The experimental data are compared with the results of theoretical calculations using DFT B3LYP/6-31G(d,p) and fast semi-empirical DFTB/GFN2-xTB method in various solvents. View Full-Text
Keywords: resorcin[4]arene; crystallographic structure; conformation; DFT calculation; energy resorcin[4]arene; crystallographic structure; conformation; DFT calculation; energy
Show Figures

Graphical abstract

MDPI and ACS Style

Szafraniec, A.; Grajda, M.; Jędrzejewska, H.; Szumna, A.; Iwanek, W. Enaminone Substituted Resorcin[4]arene—Sealing of an Upper-Rim with a Directional System of Hydrogen-Bonds. Int. J. Mol. Sci. 2020, 21, 7494. https://doi.org/10.3390/ijms21207494

AMA Style

Szafraniec A, Grajda M, Jędrzejewska H, Szumna A, Iwanek W. Enaminone Substituted Resorcin[4]arene—Sealing of an Upper-Rim with a Directional System of Hydrogen-Bonds. International Journal of Molecular Sciences. 2020; 21(20):7494. https://doi.org/10.3390/ijms21207494

Chicago/Turabian Style

Szafraniec, Anna, Marcin Grajda, Hanna Jędrzejewska, Agnieszka Szumna, and Waldemar Iwanek. 2020. "Enaminone Substituted Resorcin[4]arene—Sealing of an Upper-Rim with a Directional System of Hydrogen-Bonds" International Journal of Molecular Sciences 21, no. 20: 7494. https://doi.org/10.3390/ijms21207494

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop