Cyclooligomeric phenol-aldehyde condensation products I

Erdtman, H.; Högberg, Sverker; Abrahamsson, Sixten; Nilsson, Bo

doi:10.1016/s0040-4039(01)99028-8

Cited by 85 publications

(53 citation statements)

References 2 publications

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“…[17,18] Resorcinarene 2 was prepared according to earlier reported procedures. [14,19] Resorcinarene 1 was dissolved in methanol and resorcinarene 2 in dimethyl sulfoxide (DMSO).…”

Section: Methodsmentioning

confidence: 99%

Size‐ and Structure‐Selective Noncovalent Recognition of Saccharides by Tetraethyl and Tetraphenyl Resorcinarenes in the Gas Phase

Kalenius

Kekäläinen

Neitola

et al. 2008

Chemistry A European J

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The noncovalent complexation of tetraethyl and tetraphenyl resorcinarenes with mono-, di-, and oligosaccharides was studied with negative-polarization electrospray ionization quadrupole ion trap and electrospray ionization Fourier-transform ion cyclotron resonance mass-spectrometric analysis. The saccharides formed 1:1 complexes with deprotonated resorcinarenes, which exhibited clear size and structure selectivity in their complexation. In the case of the monosaccharides, hexoses formed much more abundant and kinetically stable complexes than pentoses or deoxyhexoses. A comparison of the mono-, di-, and oligosaccharides revealed that both the relative abundance and stability of the complexes increase up to biose and triose, but start to decrease after that point, as the length of the oligosaccharide is increased. This behavior was rationalized by comparing the lowest-energy conformations of the complexes formed between the resorcinarene and oligosaccharides. This comparison was achieved by using theoretical calculations and X-ray crystal studies.

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“…[17,18] Resorcinarene 2 was prepared according to earlier reported procedures. [14,19] Resorcinarene 1 was dissolved in methanol and resorcinarene 2 in dimethyl sulfoxide (DMSO).…”

Section: Methodsmentioning

confidence: 99%

Size‐ and Structure‐Selective Noncovalent Recognition of Saccharides by Tetraethyl and Tetraphenyl Resorcinarenes in the Gas Phase

Kalenius

Kekäläinen

Neitola

et al. 2008

Chemistry A European J

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“…Calix [4]resorcarenes (resorcinarenes) are versatile compounds often obtained from the condensation reaction of resorcinol and aldehydes (aliphatic or aromatic) in acidic medium. 1 The general reaction was reported by Baeyer 2,3 in 1872.…”

Section: Introductionmentioning

confidence: 99%

Resorcarene-Based Receptor: Versatile Behavior in Its Interaction with Heavy and Soft Metal Cations

et al. 2006

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Standard solution Gibbs energies, DeltasG degrees, of the resorcarene-based receptor 5,11,17,23-ethylthiomethylated calix[4]resorcarene, (characterized by 1H NMR and X-ray diffraction studies) in its monomeric state (established through partition experiments) in various solvents are for the first time reported in the area of resorcarene chemistry. Transfer Gibbs energies of from hexane (reference solvent) to other medium are calculated. Agreement between DeltatG degrees (referred to the pure solvents) and standard partition Gibbs energies, DeltapG degrees (solvent mutually saturated) is found. Cation-ligand interactions were investigated through 1H NMR (CD3CN and CD3OD) and conductometric titrations in acetonitrile and methanol. 1H NMR data revealed the sites of interaction of with the metal cation. The composition of the metal-ion complexes (Ag+ and Pb2+ in acetonitrile and Ag+ and Cu2+ in methanol) was established through conductometric titrations. Thus, complexes of 1:1 stoichiometry were formed between and Ag+ and Pb2+ in acetonitrile and Cu2+ in methanol. However, in moving from acetonitrile to methanol, the composition of the silver complex was altered. Thus, two metal cations are hosted by a unit of the ligand. As far as Cu2+ and in acetonitrile is concerned, conductance data suggest that metalates are formed in which up to four units of Cu2+ are taken up per unit of resorcarene. The contrasting behavior of with Cu2+ in acetonitrile relative to methanol is discussed. As far as mercury (II) is concerned, the unusual jump in conductance observed in the titration of Hg2+ with in acetonitrile and methanol after the formation of a multicharged complex (undefined composition) is attributed to the presence of highly charged smaller units (higher mobility) resulting from the departure of pendant arms from the resorcarene backbone. Isolation of these species followed by X-ray diffraction studies corroborated this statement. The thermodynamic characterization of metal-ion complexes of Ag+ and Pb2+ in acetonitrile and Cu2+ and Ag+ in methanol is reported. Final conclusions are given.

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“…Erdtman et at. finally proved the metacyclophane structure 1 of derivatives [5] by X-ray analysis. In 1980 Hogberg published his NMR studies on the conformational changes of the corresponding esters in chloroform solution [6a] and also clarified some of the acid-catalyzed rearrangememts of the stereoisomers [6b], which later were all characterized, in particular by Mann et at.…”

Section: Introductionmentioning

confidence: 86%

The Host-Guest Chemistry of Resorcinarenes [1]

Schneider

1994

Calixarenes 50th Anniversary: Commemorative Issue

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Abstract. Conformations, acid-base and supramolecular properties of phenolic metacyclophanes obtained from the condensation of resorcinol with aldehydes are discussed, including the mechanisms involved in the formation of these macrocycles. The strong binding of choline-type compounds and the inhibition of acetylcholine hydrolysis with the rccc stereoisomers is mechanistically evaluated; a rctt isomer shows strong conformational coupling for, e.g., choline binding and simultaneous proton release. The presence of larger alkyl residues at the bottom of the rccc macrocycle leads to an additional binding site for small lipophilic substrates, which is independent of the upper complexation center for positively charged substrates. Substitution at the upper rim by carboxylic groups at the 2-position of the phenyl rings yields receptors for, e.g., a, w-diammonium ions with alternate equatorial and axial arylunits. Positively charged substituents at the upper rim, introduced by aminoalkylation, lead to little change of complexation as a result from their orientation away from the binding center. Aminoacid substituents, for the same reason, do not lead to enantioselective complexation, but allow particularly for strong binding of transition metal ions. Preliminary studies show that resorcinarenes bearing a wide array of positive charges are potent groove binders to ds-DNA without intercalative contributions.

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Cyclooligomeric phenol-aldehyde condensation products I

Cited by 85 publications

References 2 publications

Size‐ and Structure‐Selective Noncovalent Recognition of Saccharides by Tetraethyl and Tetraphenyl Resorcinarenes in the Gas Phase

Size‐ and Structure‐Selective Noncovalent Recognition of Saccharides by Tetraethyl and Tetraphenyl Resorcinarenes in the Gas Phase

Resorcarene-Based Receptor: Versatile Behavior in Its Interaction with Heavy and Soft Metal Cations

The Host-Guest Chemistry of Resorcinarenes [1]

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