Thermodynamics of Calixarene Chemistry

Namor, Angela F. Danil de; Cleverley, Robert M.; Zapata-Ormachea, Mariel L.

doi:10.1021/cr970095w

Cited by 338 publications

(372 citation statements)

References 91 publications

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“…The loss of methanol from protonated N-acetyl O-methoxy proline, with a same group as in 1 (-COOCH 3 ) was reported by I. Komáromi et al 29 The possible explanation for the loss of 28 Da from ion with m/z 259 can be the migration of alkyl group followed by the loss of CO, as was observed in the metastable ion dissociation of acetylphenyl ions, CH 3 Croat. Chem.…”

Section: +supporting

confidence: 63%

“…21,24 The solvents, acetonitrile and methanol, both HPLC grade, were purchased from J. T. Baker and used without further purification. The salts were nitrates (La(NO 3 ) 3 , Kemika) and formic acid (w = 0.1 %, Kemika).…”

Section: Methodsmentioning

confidence: 99%

“…[1][2][3] Depending on a macrocyclic cavity size and substituents at upper or lower rim, calixarenes are suitable receptors for cations, 4,5 anions, 6 neutral 7 and chiral 8 molecules. Binding properties of these compounds were extensively studied by NMR, UV-Vis, vibrational and luminescence spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

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ESI MS/MS Study of Calix[4]arene Derivatives and their Metal Complexes

Benković¹,

Tomišić²,

Frkanec³

et al. 2012

Croat. Chem. Acta

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, Yb 3+ ) were analyzed by ESI MS. The influences of the solvent (acetonitrile, methanol, addition of formic acid or sodium acetate) and the calixarene:cation molar ratio on signal intensities were investigated. Comprehensive MS/MS analyses were performed of all singly and doubly charged ions of 1-3 and their complexes, and fragmentation pathways were proposed. An inductive cleavage was observed during dissociation of protonated ions, while the presence of alkali-metal or lanthanide cations caused homolytic cleavage and formation of radical cations. The results of MS analysis were in accordance with those obtained by other techniques (spectrophotometric, potentiometric, and conductometric titrations). The MS/MS experiments could be used as fast and sensitive method for prediction of relative stabilities of calixarene complexes with metal ions. (doi: 10.5562/cca2125)

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Section: +supporting

confidence: 63%

Section: Methodsmentioning

confidence: 99%

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ESI MS/MS Study of Calix[4]arene Derivatives and their Metal Complexes

Benković¹,

Tomišić²,

Frkanec³

et al. 2012

Croat. Chem. Acta

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“…[5][6][7][8][9]73 The thermodynamics of complexation of calix[n]arene derivatives and metal cations in non-aqueous solvents have been investigated and reviewed in 1998. 2 As far as calix [4]arene amide derivatives are concerned until then only quantitative data for p-tert-butyl-tetraacetamide, L1 and alkali-metal cations, Ag (I) and Ba (II) in methanol and Rb (I) Cs (I) and Ag (I) in acetonitrile have been reported. 74 From the information given for Ca(II) and Sr(II) in methanol (log K s ≥ 9), Li(I), Na(I) and K(I) (log K s ≥ 8.5) in acetonitrile at 298.15 K it can be concluded that high stability complexes are formed in these solvents.…”

Section: Calix[n]arene Tertiary Amide Derivatives Solution Studiesmentioning

confidence: 99%

“…The role of solvation in complexation processes has been emphasized in several papers. 2,4,76,77 Therefore given that the ∆ s Gº values involves the contribution of solvation and crystal lattice Gibbs energies, the latter is eliminated by the calculation of the transfer Gibbs ener-gies, ∆ t Gº using acetonitrile as the reference solvent. Data are shown in Table 1.…”

Section: Calix[n]arene Tertiary Amide Derivatives Solution Studiesmentioning

confidence: 99%

An Enchiridion of Supramolecular Thermodynamics: Calix[N]arene (N=4,5,6) Tertiary Amide Derivatives and their Ionic Recognition

Namor¹,

Matsufuji-Yasuda²,

Zegarra-Fernandez³

et al. 2013

Croat. Chem. Acta

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Abstract. The importance of detailed thermodynamic studies in assessing the selective behaviour of macrocyclic receptors for one species relative to another in a given solvent and the medium effect on complexation processes involving ionic species are emphasised. Factors to be considered in the determination of thermodynamic parameters of complexation in non-aqueous solvents are highlighted. Particular reference is made to the need for considering the bulk of information available in the literature on the solution properties of electrolytes in non-aqueous medium in the selection of the solvent for ion complexation processes involving macrocycles.A detailed thermodynamic study on the interaction of p-tert-butyl calix[n]arene (n = 4−6) tertiary amide derivatives with uni-and bivalent cations in protic (methanol) and dipolar aprotic (acetonitrile) media is reported. It is demonstrated that as the number of phenyl units in the macrocycle increases, the vital feature of the cyclic tetramer receptor for selective recognition of cations decreases significantly for the cyclic pentamer and almost disappears for the hexamer. Concluding remarks are included. (doi: 10.5562/cca2170)

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