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

Anna SzafraniecMarcin GrajdaHanna JędrzejewskaAgnieszka SzumnaWaldemar Iwanek
Published in: International journal of molecular sciences (2020)
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.
Keyphrases
  • crystal structure
  • solid state
  • water soluble
  • density functional theory
  • molecular docking
  • ionic liquid
  • molecular dynamics
  • molecular dynamics simulations
  • heat stress
  • big data
  • solar cells