Deprotonation of resorcinarenes by mono- and diamine bases: complexation and intermolecular interactions in the solid state

Abstract

The deprotonation of a resorcinarene by small organic bases results in 1 : 1 inclusion and 1 : 2 pseudo-capsular ion-pair complexes.

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

“…25 Dimethylpiperazine has been shown to deprotonate resorcinarenes and templates a directly hydrogen bonded assembly. 36 In this assembly, the protonated -NH is directly hydrogen bonded to the hydroxyl groups of the resorcinarenes (NH···O) leading to a pseudocapsular dimeric assembly. 36 Host-guest complexes between unfunctionalized resorcinarenes and secondary ammonium cations are very poorly studied.…”

“…25 Dimethylpiperazine has been shown to deprotonate resorcinarenes and templates a directly hydrogen bonded assembly. 36 In this assembly, the protonated -NH is directly hydrogen bonded to the hydroxyl groups of the resorcinarenes (NH⋯O), leading to a pseudocapsular dimeric assembly. 36 Despite the multitude of reported structures involving quaternary ammonium salts and unfunctionalized resorcinarenes and pyrogallarenes, there are limited reports on hostguest complexes with primary 30 and tertiary 35,[37][38][39] ammonium cations.…”

“…36 In this assembly, the protonated -NH is directly hydrogen bonded to the hydroxyl groups of the resorcinarenes (NH⋯O), leading to a pseudocapsular dimeric assembly. 36 Despite the multitude of reported structures involving quaternary ammonium salts and unfunctionalized resorcinarenes and pyrogallarenes, there are limited reports on hostguest complexes with primary 30 and tertiary 35,[37][38][39] ammonium cations. Host-guest complexes of unfunctionalized resorcinarenes and secondary ammonium cations are very poorly studied.…”

2-Methylresorcinarene: a very high packing coefficient in a mono-anion based dimeric capsule and the X-ray crystal structure of the tetra-anion

“…Along these lines, we have previously reported the structures of monoand di-deprotonated core resorcinarenes using mono-and diamine bases in the solid state. 13 In this contribution, we report the preparation, X-ray crystal structures and the electrospray ionization mass spectrometry (ESI-MS) characterization of mono-(1) and tetra-anions (2) as their trans-1,4-diammoniumcyclohexane, (TDAC) 2+ , complexes obtained by reacting 2-methylresorcinarene, 2-MeC2, and trans-1,4-diaminocyclohexane, TDAC, as shown in Fig. 1.…”

“…S4 for crystal structures), thus manifesting positional 50 : 50 disorder within the same unit cell. However both 2a and 2b have the same orientation in the unit cell so that the oxygen atoms O6 (50%) and O25 (50%) accept three hydrogen bonds 13 as shown in Fig. 3.…”