1,4-Phenylene-bis-(3,4-dichloro-5-phenylcarbamoyl-1H-pyrrole-2-carboxamide) bis(tetrabutylammonium chloride) acetonitrile disolvate

Abstract

The title compound, C30H20N6O4Cl4.2C16H36N+·2Cl−·2C2H3N, contains two hydrogen‐bonded chloride anions bound to 1,4‐phenyl­ene‐bis‐(3,4‐di­chloro‐5‐phenyl­carbamoyl‐1H‐pyrrole‐2‐carbox­amide) as the tetra­butyl­ammonium salt. There is also a short pyrrolic hydrogen bond (N⋯Cl = 3.068 (3) Å), and two longer ones to the amino H atoms [N⋯Cl = 3.269 (3) Å and 3.275 (3) Å]. The neutral mol­ecule lies on an inversion centre situated at the centre of the central benzene ring.

Amidopyrroles: from anion receptors to membrane transport agents

“…Additionally, crystals of the tetrabutylammonium chloride salt of receptor 13 were obtained by slow evaporation of an acetonitrile solution of the receptor in the presence of excess tetrabutylammonium chloride. 22 The complex is shown in Fig. 6 revealing that in the solid state in this complex each chloride is bound by three NH hydrogen bonds.…”

“…Orthogonal hydrogen bonded systems such as [(10 2 H + )] 22 2 are quite rare and we therefore wished to investigate if this supramolecular synthon would occur in other systems containing 2,5-bisamido-3,4-dichloropyrroles upon deprotonation. Consequently pyrrole dimers 12 and 13 were synthesised from 1,3-phenylene diamine and 1,4-phenylene diamine respectively.…”

“…Early examples of amidopyrrole containing anion receptors (19)(20)(21)(22) from Jonathan Sessler's group also contain ferrocene and were used as electrochemical anion sensors. 27 Stability constants for 20-22 were determined by 1 H NMR titrations performed in dichloromethane-d 2 /2% DMSO-d 6 and revealed a general increase in the binding affinity for dihydrogen phosphate with increasing numbers of oxygen atoms in the ethylene oxide based linker.…”

Acyclic Oligopyrrolic Anion Receptors

“…In the solid state, the two half molecules are essentially planar, whereas the complete molecule is twisted such that the angle between the pyrrole rings is 61.79(5) [58]. Further, single-crystal X-ray analysis of the Cl À complex of p-phenylene-bridged 18 as a TBA salt shows a [1 + 2]-type binding mode [59]. The molecular structures of protonated and Cl À complexes were also supported by the theoretical studies of Navakhun and Ruangpornvisuti [60,61].…”