A Complex between C-Methylcalix[4]resorcinarene and Triethylammonium Nitrate

Thuéry, Pierre; Nierlich, Martine

doi:10.1080/10610270008049128

Cited by 7 publications

(2 citation statements)

References 15 publications

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“…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.…”

Section: Introductionmentioning

confidence: 99%

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

2015

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The binding of different categories of alkyl ammonium (secondary and tertiary mono-and diammonium) salts by resorcinarenes and a pyrogallarene through weak interactions were analysed in all phases. 1 H NMR spectroscopy and electrospray ionisation mass spectrometry were utilized in analysing the complexes in solution and in the gas phase respectively. The 1 H NMR titration studies in methanol-d 4 reveal the association constants for the 1:1 complexes to vary according to the electronic properties of hosts as well as the size, geometric orientation and charge concentration of the guest cations with binding constants of up to 950 M -1 in some cases. Mass spectrometry reveals 1:1 monomeric and 1:2 dimeric complexes in the gas phase. Six co-crystals, three of which are dimeric host-guest capsular assemblies, two open inclusion complexes and a pseudocapsular methanol solvate were analysed in the solid state through single-crystal X-ray diffraction. The crystal structures confirm the complexes to be held together by multiple cation···π, CH···π and hydrogen bond interactions.

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Section: Introductionmentioning

confidence: 99%

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

2015

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“…C-Methylcalix[4]resorcinarene (Figure ), hereafter abbreviated CAL-Me, is the simplest member of the resorcinarene compounds. A solid-state structure of CAL-Me cocrystallized with various small molecules, e.g., solvents, has been exclusively studied using X-ray crystallography. − ,− Recent X-ray diffraction studies showed a dramatic effect of water and CH 3 CN exerted on C-alkylpyrogallol[4]arene assemblies by means of intermolecular hydrogen bonding.…”

Section: Introductionmentioning

confidence: 99%

X-ray Diffraction, FT-IR, and ¹³C CP/MAS NMR Structural Studies of Solvated and Desolvated C-Methylcalix[4]resorcinarene

et al. 2010

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Solid C-methylcalix[4]resorcinarene solvated by acetonitrile and water (CAL-Me) and then modified by slow solvent evaporation (CAL-Me*) was studied using single-crystal and powder X-ray diffraction, FT-IR, and (13)C CP/MAS NMR. The CAL-Me solvate crystallizes in the monoclinic P2(1)/n space group with three CH(3)CN and two H(2)O molecules in the asymmetric part of the unit cell. The CAL-Me molecules adopt a typical crown conformation with all of the hydroxyl groups of the aryl rings oriented up and all of the methyl groups disposed down (the rccc isomeric form). The crystalline network is formed by resorcinarene, CH(3)CN, and H(2)O molecules and assembled by intermolecular hydrogen bonds and weak C-H...A or C-H...pi interactions. The desolvated CAL-Me* loses its crystalline character and becomes partly amorphous. It is devoid of CH(3)CN and deficient in water. However, the resorcinarene molecules still remain in the crown conformation supported by intramolecular hydrogen bonds, while intermolecular hydrogen bonds are considerably disintegrated. The work directs general attention to the problem of stability and polymorphism of resorcinarene solvates. It shows that the joint use of diffractometric and spectroscopic methods is advantageous in the structural studies of complex crystalline macromolecular systems. On the other hand, the solid-state IR and NMR spectroscopic analyses applied in tandem have been found highly beneficial to elucidate the disordered structure of poorly crystalline, desolvated resorcinarene.

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Resorcarenes in the Boat Conformation as Building Blocks for Hydrogen-Bonded Assemblies Including Two Ammonium Cations

et al. 2001

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Crystal structures are reported for various co-crystals of rccc-resorcarenes with triethylammonium chloride. Usually, two molecules of a C2v-symmetric tetraester 2 in the boat conformation are linked through four hydrogen-bonded chloride anions to give dimeric assemblies. Two of the chloride anions may be replaced by four hydrogen-bonded ethanol molecules in an otherwise similar structure. These assemblies, which consist of six or eight components, posses voluminous, negatively charged chambers in which two triethylammionium cations, 3+, are included as guests by strong electrostatic and hydrogen-bonding interactions. The host-guest N-H...Cl hydrogen bonds were clearly detected at 173 K. These are the first examples of hydrogen-bonded, solid-state capsules trapping two ions of the same charge in close proximity. In the 1:2 complex with 3+ Cl-, the molecule of the parent resorcarene 1 also adopts a boat conformation whose cavity is considerably extended by four hydrogen-bonded chloride anions. The pocket formed in this way again includes two 3+ ions as a result of electrostatic and hydrogen bonding host-guest interactions. All these structures show that the boat conformers of resorcarenes can be used as a novel motif for the construction of hydrogen-bonded assemblies capable of molecular inclusion and encapsulation.

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A Complex between C-Methylcalix[4]resorcinarene and Triethylammonium Nitrate

Cited by 7 publications

References 15 publications

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

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

X-ray Diffraction, FT-IR, and ¹³C CP/MAS NMR Structural Studies of Solvated and Desolvated C-Methylcalix[4]resorcinarene

Resorcarenes in the Boat Conformation as Building Blocks for Hydrogen-Bonded Assemblies Including Two Ammonium Cations

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A Complex between C-Methylcalix[4]resorcinarene and Triethylammonium Nitrate

Cited by 7 publications

References 15 publications

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

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

X-ray Diffraction, FT-IR, and 13C CP/MAS NMR Structural Studies of Solvated and Desolvated C-Methylcalix[4]resorcinarene

Resorcarenes in the Boat Conformation as Building Blocks for Hydrogen-Bonded Assemblies Including Two Ammonium Cations

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X-ray Diffraction, FT-IR, and ¹³C CP/MAS NMR Structural Studies of Solvated and Desolvated C-Methylcalix[4]resorcinarene