Complexation of adamantane-ammonium substrates by beta-cyclodextrin and itsO-methylated derivatives

Gelb, Robert I.; Schwartz, Lowell M.

doi:10.1007/bf01080464

Cited by 54 publications

(41 citation statements)

References 12 publications

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“…The positive entropy value for S2 is attributed to an overall net release of hydration to the bulk solvent because apolar guests with greater LSA often display an optimal size-fit relationship with the β-CD cavity interior. 45 In Figure 3c, S3 displays an intermediate absorbance change when compared to S1 and S2, where the change in absorbance is more pronounced for S2. A maximum amount of phth is displaced when [S3] o reaches ∼5.0 mM; this concentration is 3-fold higher relative to S2 and 5-fold smaller than that for S1.…”

Section: ■ Results and Discussionmentioning

confidence: 93%

Thermodynamic Properties of Inclusion Complexes between β-Cyclodextrin and Naphthenic Acid Fraction Components

et al. 2015

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The spectral displacement technique was used to determine the 1:1 equilibrium binding constants (K 2 ) of the complexes formed between β-cyclodextrin and carboxylate anion guests, including either single components or mixtures in aqueous solution at variable temperatures (25−55°C). A van't Hoff analysis of the results afforded thermodyamic parameters (ΔH°, ΔS°, and ΔG°) of the single-component carboxylate anions and complex mixtures of carboxylic acid species, referred to as naphthenic acids (NAs). Three types of single-component examples of NAs with variable hydrogen deficiency (z) values were studied: n-octanoic (z = 0; S1), trans-4-pentylcyclohexanecarboxylic acid (z = −2; S2), and dicyclohexylacetic acid (z = −4; S3). The carboxylate anion mixtures were obtained from commercial suppliers and an industrial source obtained from oil sands process water. The estimated K 2 values decrease with increasing temperature, and the standard Gibbs energy change (ΔG°) for complex formation is generally favorable (from −16 to −28 kJ/mol) and largely enthalpy-driven (from −12 to −30 kJ/mol). The change in entropy of complex formation (ΔS°) for S1, S2, and S3 varies (−23 and 44 J mol −1 K −1 ) depending on the guest size and relative lipophilicity. The positive correlation between complex stability, host−guest size-fit complementarity, and lipophilicity of the carboxylate anion reveals the importance of the hydrophobic effect, as evidenced by compensation phenomena for such host−guest complexes.

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Section: ■ Results and Discussionmentioning

confidence: 93%

Thermodynamic Properties of Inclusion Complexes between β-Cyclodextrin and Naphthenic Acid Fraction Components

et al. 2015

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“…[300][301][302] In carboxy-substituted substrates of this type two binding sites existsthe carboxylic acid and the alicyclic portionsand so both 1:1 and 1:2 binding can take place. 301 Some of the binding constants are very large, presumably as a result of a close match of the alicyclic group to the CyD cavity.…”

Section: Structural Studiesmentioning

confidence: 99%

The Stability of Cyclodextrin Complexes in Solution

1997

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“…β-Cyclodextrin (β-CD, 1 ), the cyclic α(1→4) heptamer of glucose, is known to form inclusion compounds with a great variety of guests [1], such as derivatives of benzene [2–3], cyclohexane [4], adamantane [5–6], other alicyclic guests [7], and also inorganic molecules or ions [1,8]. …”

Section: Introductionmentioning

confidence: 99%

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

Fourmentin¹,

Ciobanu

Landy³

et al. 2013

Beilstein J. Org. Chem.

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SummaryThe inclusion of volatile derivatives of benzene and cyclohexane in β-cyclodextrin (β-CD), hydroxypropyl-β-CD, and hydrophilic β-CD-thioethers was investigated by static headspace gas chromatography (HS-GC) and molecular modelling. The obtained binding constants strongly increase with the amount of space filling of the CD cavity and the salt concentration. β-CD thioethers show a 3–10 times higher binding potential than native β-CD.

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Complexation of adamantane-ammonium substrates by beta-cyclodextrin and itsO-methylated derivatives

Cited by 54 publications

References 12 publications

Thermodynamic Properties of Inclusion Complexes between β-Cyclodextrin and Naphthenic Acid Fraction Components

Thermodynamic Properties of Inclusion Complexes between β-Cyclodextrin and Naphthenic Acid Fraction Components

The Stability of Cyclodextrin Complexes in Solution

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

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