New lower rim calix [4]arene amine derivatives: synthesis, characterisation and acid–base properties. Potential anion and cation binders

Namor, Angela F. Danil de; Velarde, Félix J. Sueros; Cabaleiro, Mercedes C.

doi:10.1039/ft9969201731

Cited by 15 publications

(11 citation statements)

References 22 publications

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“…philic cavity is achieved through the interaction of the Agì on with the electron lone pair of the pyridine nitrogen atom [d(AgÉ É ÉN) \ 2.483 (5) The strength of this interaction is Ó]. optimised by rotation of the pyridine molecule around the pivotal group of the residue so as to leave the CH 2 OCH 2 Py Ag`ion practically on the plane deÐned by the pyridine ring [at 0.080 (1) As a result of the complexing interactions, Ó]. Ag`is encapsulated within a polyhedral cage with the form of a distorted Archimedean square antiprism.…”

Section: X-ray Crystallography Of the Silver Monoacetonitrile Complex...mentioning

confidence: 99%

Solution thermodynamics of geometrical isomers of pyridino calix(4)arenes and their interaction with the silver cation. The X-ray structure of a 1:1 complex of silver perchlorate and acetonitrile with 5,11,17,23-tetra-tert-butyl-[25,26,27,28-tetrakis(2- pyridylmethyl)oxy]calix(4)arene

Namor¹,

Piro²,

Salazar³

et al. 1998

Faraday Trans.

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The solubility and derived standard Gibbs energies of solution of three geometrical isomers of pyridinocalix(4)arenes M5,11,17,23-tert-butyl-[25,26,27,28-tetrakis-(n-pyridylmethyl) oxy]-p-tert-butylcalix(4) arene, with n \ 2, 3, 4N in a variety of solvents at 298.15 K are reported. Solvation e †ects are assessed from the standard transfer Gibbs energies of these ligands, using acetonitrile as the reference solvent. For the 2-pyridyl derivative in alcohols as the aliphatic chain length of the alcohol increases, the extent of solventÈligand interaction increases, whereas for the 3-and the 4-pyridyl derivatives the opposite is observed. The protonation constants for the 4-pyridyl derivative in methanol at 298.15 K are reported. The results, compared with corresponding values for the 3-pyridyl derivative show that the basic character of these ligands follows the sequence ; 4-pyridyl [ 3-pyridyl [ 2-pyridyl calix(4)arene. Thermodynamic parameters for the complexation of these macrocycles (2 and 4-pyridyl derivatives) and the silver cation in acetonitrile show that, as the distance between the phenolic oxygens and the pyridyl nitrogens increases, the strength of complexation decreases. Thermodynamic data for the complexation of silver and the 2-pyridylcalix(4)arene derivative are compared with corresponding values for sodium and this ligand in the same solvent. The results suggest that the 2-pyridyl derivative provides phenolic oxygens and pyridyl nitrogens as the active sites for complexation with silver. This is corroborated by 1H NMR measurements of this ligand and silver in at 298 K. CD 3 CN The crystal structure of a 1 : 1 monoacetonitrile and silver complex of the 2-pyridyl derivative with perchlorate as the counter-ion has been determined from XRD data. The substance crystallises in the tetragonal space group P4/n with a \ 15.580(2) c \ 13.082(2) and z \ 2. The macrocycle is sited on a Ó, Ó, fourfold symmetry axis and consists of two conical parts, one hydrophobic, Ðlled with an acetonitrile molecule, the other hydrophilic, encapsulating the Ag`ion through the ethereal oxygen [d(AgÉ É ÉO) \ 2.923(3) and Ó] pyridine nitrogen atoms [d(AgÉ É ÉN) \ 2.483(5)The coordination around the Ag`ion has the form of a Ó]. distorted Archimedean square antiprism. The ability of the macrocycle to complex the silver cation in its hydrophilic cavity is demonstrated.

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Section: X-ray Crystallography Of the Silver Monoacetonitrile Complex...mentioning

confidence: 99%

Solution thermodynamics of geometrical isomers of pyridino calix(4)arenes and their interaction with the silver cation. The X-ray structure of a 1:1 complex of silver perchlorate and acetonitrile with 5,11,17,23-tetra-tert-butyl-[25,26,27,28-tetrakis(2- pyridylmethyl)oxy]calix(4)arene

Namor¹,

Piro²,

Salazar³

et al. 1998

Faraday Trans.

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“…Selecting the receptor Among the various calix [4]arene derivatives tested, 1 and 2 showed the highest affinity with the proton. 31 Due to the very low solubility of the receptors in water, 1 H NMR measurements were carried out to assess the interaction between 1 and the herbicides in a dipolar aprotic solvent, deuterated acetonitrile (CD 3 CN), and in a protic solvent, deuterated methanol (CD 3 OD). Except for NAA and BU for which no chemical shi changes were observed, signicant downeld chemical shi changes relative to the free receptor (proton numbers for the receptor are shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The attachment of calix [4]arenes through their lower or upper rim to silica has been the subject of several papers [24][25][26][27][28] and book chapters reported in the literature. [25][26][27][28][29][30] In this paper we report solution ( 1 H NMR, conductance measurements) and solid state (structural X-ray diffraction) studies on the interaction of a lower rim partially 'tertiary amine' functionalised calix [4]arene, 5,11,17,23-tetra-tert-butyl 25,27-bis(diethylamino)ethoxy-26,28dihydroxy calix [4]arene, 1, its fully substituted calix [4]arene counterpart: 5,11,17,23-tetra-tert-butyl 25,26,27,28-(diethyllamino)ethoxy calix [4]arene, 2, [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] and their interaction with phenoxyacid herbicides.…”

Section: Introductionmentioning

confidence: 99%

Calix[4]arene amine modified silica: from fundamentals to new recyclable materials for the removal of chlorophenoxy acids from water

et al. 2015

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“…Calix(4)arene amino derivatives were synthesised as described elsewhere. 15,16 The silver perchlorate salt (Aldrich) was left over P 4 O 10 for several days, before use. Dichloromethane (Fisher Chemicals) was used for the distribution experiments.…”

Section: Experimental Chemicalsmentioning

confidence: 99%

“…In phase transfer processes using calixarene derivatives, the water-dichloromethane solvent system has often been selected to assess the extraction properties of these macrocycles for metal cations. Therefore we set out to investigate the extraction properties of a wide variety of calixarene amine derivatives 14,15…”

Section: Introductionmentioning

confidence: 99%

Extraction of silver (I) by calixarene amine derivatives: The medium effect on the stoichiometry of the phase transfer extraction process

Namor

Goitia

Casal

et al. 2001

Phys. Chem. Chem. Phys.

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New lower rim calix [4]arene amine derivatives: synthesis, characterisation and acid–base properties. Potential anion and cation binders

Cited by 15 publications

References 22 publications

Solution thermodynamics of geometrical isomers of pyridino calix(4)arenes and their interaction with the silver cation. The X-ray structure of a 1:1 complex of silver perchlorate and acetonitrile with 5,11,17,23-tetra-tert-butyl-[25,26,27,28-tetrakis(2- pyridylmethyl)oxy]calix(4)arene

Solution thermodynamics of geometrical isomers of pyridino calix(4)arenes and their interaction with the silver cation. The X-ray structure of a 1:1 complex of silver perchlorate and acetonitrile with 5,11,17,23-tetra-tert-butyl-[25,26,27,28-tetrakis(2- pyridylmethyl)oxy]calix(4)arene

Calix[4]arene amine modified silica: from fundamentals to new recyclable materials for the removal of chlorophenoxy acids from water

Extraction of silver (I) by calixarene amine derivatives: The medium effect on the stoichiometry of the phase transfer extraction process

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