Host–Guest Complexes between Calix[4]arenes Derived from Resorcinol and Alkylammonium Ions

Lippmann, Tino; Wilde, H.; Pink, Maren; Schäfer, Andrea; Hesse, Manfred; Mann, G.

doi:10.1002/anie.199311951

Cited by 63 publications

(17 citation statements)

References 17 publications

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“…This network never extends to more than three ionic species. The present structure can be compared to that of l.(HNEt&(SO;-).4EtOH (3) previously reported [7]. The intramolecular hydrogen bonds in the calix[4lresorcinarene~ unit are the same in both structures; the small differences between the torsion angles in the two compounds (given in Tab.…”

Section: Resultsmentioning

confidence: 84%

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

Thuéry

Nierlich

2000

Supramolecular Chemistry

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The synthesis and crystal structure of the complex formed by the all-cis epimer of C-methylcalix[4lre-sorcinarene (1) and triethylammonium nitrate are reported. "1.(HNEt:)4 . (NO; )1(2)", crystallizes in the monoclinic space group PZ1/n, a= 25.796(2), b= 16.6048(1!), c= 29.5659(10) A, / I = 94.636(4)', V= 12623(2) A', Z= 8. Refinement led to a final conventional R1 value of 0.128 for 12428 reflections and 1473parameters. The resorcinarene displays the usual bowl-type shape, with four hydroxyl protons involved in intramolecular hydrogen bonds, whereas the remaining four make hydrogen bonds with four bridging nitrate ions, which results in the formation of infinite chains. Those chains are arranged so as to form layers, between which the triethylammonium ions and the remaining nitrate ions are hydrogenbonded one to another.

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Section: Resultsmentioning

confidence: 84%

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

Thuéry

Nierlich

2000

Supramolecular Chemistry

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“…The complex with pyridine [3a·6 (25)] gave suitable crystals for X-ray analysis: in the crystal structure four hydroxyl groups (e.g. the pairs 4, 24 and 12, 16) form intramolecular O-H ….…”

Section: Resorcarenes and Neutral Moleculesmentioning

confidence: 99%

Resorcarenes: Hollow Building Blocks for the Host-Guest Chemistry

Botta

Cassani

D’Acquarica

et al. 2005

COC

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The continuous search for new qualities and the desirability of controlling the size, shape and the chemical features had led to the successful synthesis of various molecular containers and their complexes starting from resorcarene skeleton. The rigidified cavitands have been extended to capture in their round hug bigger and bigger molecules. By covalent synthesis many kinds of new hosts have been built, that maintain guests in their prison for more and more long time. Self assembly, driven by metal-ligand interaction, van der Waals forces, hydrophobicity and, mainly, hydrogen bonds, is at the base of capsules, a novel type of compounds with a peculiar inner phase, stereochemistry and reactivity. The amazing variety of hollow buildings with a resorcarene-based framework and often unique properties is reviewed. OH HO 1168 Current Organic Chemistry, 2005 Botta et al. RESORCARENES AS CONTAINER 2.1 Resorcarenes and Cations or Charged MoleculesAlso resorcarenes form stable complexes with alkali metal cations (Li I , Na I , K I , Rb I , Cs I ) [14]. The interaction of simple resorcarenes with metal cations and ammonium ions has been extensively studied. The conformational change of the host resorcarene, the most favourable binding locations and the relative binding energies have been investigated by ab initio methods [15]. The same group studied the interaction with cations of resorcarene 3a, (Chart 2) in comparison with its permethylated derivative 3b, by Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (ESI-FT-ICR-MS) and ab initio calculations [16]. The significance of intramolecular hydrogen bonding for the cone conformation and the presence of intramolecular flip-flop hydrogen bonding in 3a were confirmed by calculations and ND 3 -exchange experiments. Regard to the complexation, the following items were established: i) all the above alkali metal cations formed host-guest complexes by docking inside the cavity of the host; ii) the complexation with larger cations, especially Cs + , was favoured; iii) all the cations formed stable dimer resorcarene capsules. Chart 2. Resorcarenes octol (3a) and octamethyl ether (3b).Conversely, Cu II cations were shown to interact with cyano-4a (Chart 3) and amino-resorcarenes 4b, forming in the latter case a complex with octahedrical geometry, as evidenced by the EPR spectrum; accordingly, the computercalculated structure suggested a three-molecular complex between Cu II and two molecules of 4b, in which the ligands use three of their functionalities at the lower rim to fix the ion with a distorted octahedral coordination [17]. Chart 3. Resorcarenes interacting with metal cations.The interaction of resorc[4]arenes octamethyl ethers such as 4c with Fe III in organic media was analysed by 1 H NMR studies, carried out using Ga III instead of Fe III . As a result, resorcarenes bearing carboalkyloxy groups in the side chains were shown to have two active sites of interaction, the first located at the aromatic upper rim and the other in the vicinity ...

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“…Size selectivities were obtained with various derivatized compounds [31,32]. Complexes of calix [4]arenes with alkylammonium ions have been generated directly from solution by ESI [33]. The complex of calix [4]arene with benzylammonium cation has been generated by Dearden and co-workers by gas-phase ion molecule reactions [34].…”

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Non-covalent calixarene-amino acid complexes formed by MALDI-MS

Stone

Franz

Lebrilla

2002

J. Am. Soc. Mass Spectrom.

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Non-covalent inclusion complexes formed between amino acids and derivatized calix [6]arenes are observed in MALDI mass spectrometry. The methyl, ethyl, and propyl ester derivatives of calix [6]arene yielded amino acid complexes, while the smaller calix[4]arene analogs did not. Similarly the underivatized calix[6]arene and calix[4]arene did not produce complexes. Amino acid complexes were observed for nearly all 20 amino acids in time-of-flight (TOF) analysis. In Fourier transform mass spectrometry (FTMS) analysis, however, only the most basic amino acids arginine, histidine, and lysine formed stable adducts. The complexes were abundant under matrix-assisted laser desorption ionization (MALDI) conditions, which suggested favorable interactions between host and guest. (J Am Soc Mass Spectrom 2002, 13, 964 -974)

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Host–Guest Complexes between Calix[4]arenes Derived from Resorcinol and Alkylammonium Ions

Cited by 63 publications

References 17 publications

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

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

Resorcarenes: Hollow Building Blocks for the Host-Guest Chemistry

Non-covalent calixarene-amino acid complexes formed by MALDI-MS

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