Binding features of molecular clips derived from diphenylglycoluril

Abstract

The structure and binding properties of a series of receptor molecules based on the building block diphenylglycoluril are described. These receptors bind dihydroxy-substituted aromatic guests in chloroform solution by means of hydrogen bonding and tt-tt stacking interactions. IR difference spectroscopy shows that the hydrogen bonds are formed between the OH groups of the guest molecule and the 7r-electrons of the urea carbonyl groups present in the receptor. The structure of the complexes was further investigated by comparing the complexation-induced shifts in the 'H N M R spectra with the calculated shifts for a number of geometries of the host-guest complexes. These data demonstrate that the guest molecules are clamped within the cavity of the receptor.

Binding Properties of Two Novel Phosphane-Modified Tetrapodants and Their Bimetallic Transition Metal Complexes

“…This carbonyl stretching frequency can be used to observe interactions involving the carbonyl group. For example, hydrogen bonding between the carbonyl group and resorcinol derivatives induces a shift of Ϫ25 ± 5 cm Ϫ1 , as has been described in the literature [16,21,22] . The 1 H-and 13 C-NMR spectra of 3 and 4 indicated that the concave part of the host, i.e.…”

“…Dihydroxybenzenes bind in probably responsible for the non-linear relationship between σ m and ∆G ass . They can interact with an incoming the cavity of the host molecule via hydrogen bonds between the hydroxy groups of the guest and the urea carbonyl substrate, as shown by the lineshape analyses of the 31 P{ 1 H}-NMR spectra (vide supra), and therefore influence groups of the host molecule [15,16,22] . A second interaction is π-π stacking between the aromatic walls of the host and the the association constant.…”

Toposelective synthesis under thermodynamic control and bioactivities of topoisomers based on diethoxycarbonyl glycoluril derivatives

“…Therefore, all the structures of CC, (±) CT, SC, (±) ST isomers were determined by X-ray crystallography to verify their topological structures ( Fig. 3) (C-shaped molecules have the potential to become synthetic receptors for some host-guest complexes [42][43][44][45] , so their X-ray crystal structures and binding properties are under investigation ).…”

DFT Study of the Interaction Energy Between Thioglycoluril Clip and Phenol Derivatives

“…[10][11][12][13][14][15][16] Glycoluril is known as an excellent receptor for dihydroxybenzene guest molecules due to p-p stacking interactions, hydrogen bonds and the cavity effect. [17][18][19][20] The interaction strength of these types of guests within the host can expand a wide range (Ka = 0-10 5 M −1 ), which vary with a simple modification of either the host or guest molecule. 21 It has been found that the separation of a dihydroxybenzene isomer mixture, using an ordinary column, containing silica gel as a stationary phase is impossible.…”