The formation of complexes by tetraethylresorcarene with planar guest ions studied by electrospray ionisation Fourier transform ion cyclotron resonance mass spectrometry

Mäkinen, Marko; Vainiotalo, Pirjo

doi:10.1002/rcm.1388

Cited by 5 publications

(4 citation statements)

References 38 publications

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“…In the gas phase, the ions probably lost a proton from one of the ammonium groups to decrease the repulsion between the two charged sites, and for that reason only singly charged species were observed. Similar behavior in MS measurements has been observed previously 26…”

Section: Resultssupporting

confidence: 90%

“…In earlier studies, 26 unsubstituted tetraethyl resorcarene was not observed to form complexes with the oxidized forms of p-phen and o-phen. This underlines the importance of tosylium substituents in the complexation of resorcarene 1, in line with the observations made in our study of the complexation of aliphatic ammonium ions.…”

Section: Complex Formationmentioning

confidence: 90%

“…Similar behavior in MS measurements has been observed previously. 26 In addition to an ion at the expected m/z value of 1325, addition of o-phen or p-phen to the measurement solution also gave rise to ions at m/z 1323 and 1324, which correspond to complexes containing oxidized forms of these guest ions. The spectra of arylammonium complexes and magnifications of the isotopic patterns presented in Fig.…”

Section: Complex Formationmentioning

confidence: 97%

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Noncovalent complex formation of tetratosylated resorcarene with aromatic, aliphatic, and cyclic alkyl ammonium ions: a mass spectrometric study of complex properties

Ventola

Pirskanen

Vainiotalo

2005

Rapid Comm Mass Spectrometry

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The ability of tetratosylated resorcarene to form complexes with aromatic ammonium ions was investigated by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. The formation of noncovalent complexes, [1þguest] þ and, as observed with singly charged aromatic anilinium and phenylene aminoammonium guests. Comparison of the complexation efficiencies of the aromatic and aliphatic ammonium ions showed the importance of proton affinity of conjugate amines in complex formation. In collision-induced dissociation experiments, gas-phase stability was found to be lower for complexes formed with aromatic ions and this behavior was not found to depend on the proton affinity of conjugate amines. Fast oxidation of the para and ortho aminoammonium ions and complexation of these ions with tetratosylated resorcarene was observed.

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Section: Resultssupporting

confidence: 90%

Section: Complex Formationmentioning

confidence: 90%

Section: Complex Formationmentioning

confidence: 97%

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Noncovalent complex formation of tetratosylated resorcarene with aromatic, aliphatic, and cyclic alkyl ammonium ions: a mass spectrometric study of complex properties

Ventola

Pirskanen

Vainiotalo

2005

Rapid Comm Mass Spectrometry

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“…The non-covalent interactions within these host-guest complexes require a gentle ionisation method like ESI mass spectrometry, whose results are assumed to reflect the situation in solution [62]. By this method the complexation of resorcarenes with protonated aliphatic amines was shown to occur readily [63].…”

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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Current literature in mass spectrometry

2004

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (4 Weeks journals ‐ Search completed at 7th. July 2004)

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The formation of complexes by tetraethylresorcarene with planar guest ions studied by electrospray ionisation Fourier transform ion cyclotron resonance mass spectrometry

Cited by 5 publications

References 38 publications

Noncovalent complex formation of tetratosylated resorcarene with aromatic, aliphatic, and cyclic alkyl ammonium ions: a mass spectrometric study of complex properties

Noncovalent complex formation of tetratosylated resorcarene with aromatic, aliphatic, and cyclic alkyl ammonium ions: a mass spectrometric study of complex properties

Resorcarenes: Hollow Building Blocks for the Host-Guest Chemistry

Current literature in mass spectrometry

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