Inclusion complexes of 18-crown-6 and (Na+⊂[2.2.2]cryptand) in [C-methylcalix[4]resorcinarene-Hn], n⊕=⊕0, 1

Atwood, Jerry L.; Barbour, Leonard J.; Hardie, Michaele J.; Lygris, Emmanuel; Raston, Colin L.; Webb, Helen R.

doi:10.1039/b100578m

Cited by 9 publications

(5 citation statements)

References 13 publications

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“…[2.2.2]Cryptand has been shown to act as a guest in supramolecular chemistry with C-methylresorcin [4]arene 21 and cyclotriveratrylene. 22 In these instances, the cryptand resides in the bowl of the resorcinarene and CTV host molecules.…”

Section: Dalton Full Papermentioning

confidence: 99%

Supramolecular assemblies of p-sulfonatocalix[4]arene with aquated trivalent lanthanide ions

Atwood

Barbour

Dalgarno

et al. 2002

J. Chem. Soc., Dalton Trans.

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Section: Dalton Full Papermentioning

confidence: 99%

Supramolecular assemblies of p-sulfonatocalix[4]arene with aquated trivalent lanthanide ions

Atwood

Barbour

Dalgarno

et al. 2002

J. Chem. Soc., Dalton Trans.

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“…Only the mono-deprotonated resorcinarenes under different conditions have been isolated in the solid state. [33][34][35][36] In this contribution, we present several examples of supramolecular assemblies resulting from the deprotonation of resorcinarenes by mono-and dibasic amines, viz. triethylamine, 3, and its dibasic analog, N,N′-dimethylpiperazine, 4 (Fig.…”

Section: Introductionmentioning

confidence: 99%

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

Beyeh

Valkonen

2014

CrystEngComm

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“…Thus, H 2 CTA - anions organize in a 3D host framework that houses an 18-C-6 macrocycle as the guest upon which the NH 4 + cation is perched. This (NH 4 + guest)∩ (18-C-6 cavitand)⊂(H 2 CTA - hydrate clathrand) structure of 1 is the first organic analogue (no metal ion present) of {M + ⊂18-C-6} n ⊂/∩(calix[4]arene) n - type supermolecules resembling the Russian doll . All O−H···O, N−H···O hydrogen bonds and C−H···O interactions are in their usual distance−angle range (Table ).…”

mentioning

confidence: 92%

“…This indeed turns out to be the case. H 2 CTA - ·H 2 O·NH 4 + ·18-C-6 ( 1 ) has a three-dimensional channel structure of H 2 CTA - through the inclusion of water; the channels house a crown ether and NH 4 + counterion resembling the Russian nesting doll superanion capsule−metal ion complexes reported by Atwood and Raston . The anions form undulated sheets in H 2 CTA - ·OHNH 3 + ·18-C-6 ( 2 ) with supercations intercalating the charged layers.…”

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confidence: 99%

Influence of the Ammonium Cation and 18-Crown-6 Guest on the Supramolecular Networks of 1,3,5-Cyclohexanetricarboxylic Acid

Bhogala

Nangia

2005

Crystal Growth & Design

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The title acid 1,3-cis,5-cis-cyclohexanetricarboxylic acid (H 3 CTA) forms a three-dimensional anionic host framework via O-H‚‚‚O -hydrogen bonds with 11.2 × 12.7 Å square channels for the inclusion of 18-crown-6 (18-C-6) and NH 4 + cation in a Russian doll assembled guest∩cavitand⊂clathrand crystal structure, H 2 CTA -‚H 2 O‚NH 4 + ‚18-C-6 (1). Differences in the binding of the ammonium cation to the crown ether and OHNH 3 + cation result in a two-dimensional network of H 2 CTA -anions in H 2 CTA -‚OHNH 3 + ‚18-C-6 (2) that resemble the black phosphorus topology. In contrast to ionic structures 1 and 2, crystal structure of the neutral complex H 3 CTA‚(18-C-6) 0.5 (3) is sustained by a size/shape fit of the crown macrocycle in the 14.5 × 14.5 Å hexagonal cavity of the triacid host and 12 C-H‚‚‚O interactions.We recently described crystal structures of 1,3-cis,5-cis-cyclohexanetricarboxylic acid (H 3 CTA) with some amine bases to give H 2 CTA -‚RNH 3 + salts (R ) H, NH 2 , OH, Me, Et). 1 The role of cation template was noted to be crucial in these structures. Tetrahedral ammonium cations, such as NH 4 + , OHNH 3 + , and NH 2 -NH 3 + with four strong NH/OH groups, direct a supramolecular tetrahedron of H 2 CTA -anions stabilized by O-H‚‚‚O -hydrogen bonds which in turn grows to the adamantane network. On the other hand, the MeNH 3 + counterion with only three donor groups results in a hexagonal layer structure of black phosphorus topology. Ammonium cation is known to perch on the 18-crown-6 macrocycle bonded via three N + -H‚‚‚O hydrogen bonds. 2 We reasoned that the fourth H bonding group on the hydrophobic outside-hydrophilic inside ammonium ion-18-C-6 complex would direct the organization of H 2 CTA -anions and furthermore the chairlike conformation of 18-C-6 in the solid state would match with that of cyclohexane tricarboxylic acid. This indeed turns out to be the case. H 2 CTA -‚ H 2 O‚NH 4 + ‚18-C-6 (1) has a three-dimensional channel structure of H 2 CTA -through the inclusion of water; the channels house a crown ether and NH 4 + counterion resembling the Russian nesting doll superanion capsule-metal ion complexes reported by Atwood and Raston. 3 The anions form undulated sheets in H 2 CTA -‚ OHNH 3 + ‚18-C-6 (2) with supercations intercalating the charged layers. The crystal structure of neutral host-guest complex H 3 -CTA‚(18-C-6) 0.5 (3) has a large hexagonal, chicken wire network of triacid molecules that is filled by the crown ether and stabilized via numerous C-H‚‚‚O interactions. Ermer 4 had targeted the isolation of a symmetric supramolecular hexagon in complexes of crown ether with trimesic acid (H 3 TMA) and H 3 CTA but instead obtained hydrated structures.Equimolar amounts of H 2 CTA -‚NH 4 + salt and 18-C-6 were dissolved in EtOH by gentle heating and crystallized at room temperature. Diffraction quality single crystals of hydrate 1 appeared after one week, which were solved and refined in the noncentrosymmetric space group Pna2 1 . 5 There are two molecules each of H 2 CTA -, NH 4 + , 18-C-6, ...

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Inclusion complexes of 18-crown-6 and (Na+⊂[2.2.2]cryptand) in [C-methylcalix[4]resorcinarene-Hn], n⊕=⊕0, 1

Cited by 9 publications

References 13 publications

Supramolecular assemblies of p-sulfonatocalix[4]arene with aquated trivalent lanthanide ions

Supramolecular assemblies of p-sulfonatocalix[4]arene with aquated trivalent lanthanide ions

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

Influence of the Ammonium Cation and 18-Crown-6 Guest on the Supramolecular Networks of 1,3,5-Cyclohexanetricarboxylic Acid

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