Formation, Structure, and Stability of α- and β-Cyclodextrin Inclusion Complexes of Phenol and Benzoic Acid Derivatives in Vacuo and in Water

Song, Le Xin; Wang, Hai Ming; Xu, Peng; Zhang, Zi Qiang; Liu, Qing Qing

doi:10.1246/bcsj.80.2313

Cited by 25 publications

(7 citation statements)

References 37 publications

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“…Figure 4 shows the plots of ( Table 1. For all the four inclusion systems, the dependencies were linear in the investigated concentration range, confirming that the stoichiometries of the inclusion complexes in solution were 1:1 [42,43].…”

Section: Determination Of Formation Constants Of the Inclusion Complesupporting

confidence: 63%

Interaction of naproxen with β-cyclodextrin and its derivatives/polymer: experimental and molecular modeling studies

Banik

Gogoi

Saikia

2011

J Incl Phenom Macrocycl Chem

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The interaction of naproxen with b-cyclodextrin and its derivatives (hosts) as well as polymer has been studied using UV Visible (UV-Vis), Fourier Transform Infrared (FTIR), Nuclear Magnetic Resonance (NMR) spectroscopy and Scanning electron microscopy (SEM). In this paper, the solid inclusion complexes were prepared by freeze drying method. The formation constants of the complexes were determined by UV-Vis method. The adsorption properties of naproxen with b-Cyclodextrin bonded silica stationary phase (CDS) were studied for an in-depth understanding of the host-guest interaction. The inclusion process involving naproxen and hosts was investigated by using the PM3 quantum-mechanical semiempirical method. The stabilization energy values obtained from the semiempirical calculation showed the same relation with the formation constant values determined by UV-Vis spectroscopy.

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Section: Determination Of Formation Constants Of the Inclusion Complesupporting

confidence: 63%

Interaction of naproxen with β-cyclodextrin and its derivatives/polymer: experimental and molecular modeling studies

Banik

Gogoi

Saikia

2011

J Incl Phenom Macrocycl Chem

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“…In general, selective sorption of guest molecules such as carboxylic acids is consistent with the general concept of 'size‐fit' selectivity observed in many supramolecular host‐guest systems 6, 43–46. The lipophilicity of carboxylic acid guest molecules generally increases as the molecular weight increases.…”

Section: Resultssupporting

confidence: 80%

“…4(a)–4(c)); however, the relative abundances of the 1:1 adducts containing surrogate 4 for the CD hosts are: γ ‐CD > β ‐CD ≈ α ‐CD. The formation of favourable 1:1 molecular adducts for γ ‐CD is consistent with its suitable 'size‐fit'43, 44 for larger guest molecules, compared with β ‐CD and α ‐CD. A low intensity ion ( m/z 1043.9) corresponding to the 1:1 cellobiose‐surrogate 4 complex is observed and is consistent with the increased lipophilicity of larger carboxylic acid molecules.…”

Section: Resultssupporting

confidence: 65%

Electrospray ionization mass spectrometry studies of cyclodextrin‐carboxylate ion inclusion complexes

Mohamed

Wilson

Headley³

et al. 2009

Rapid Comm Mass Spectrometry

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Aqueous solutions containing simple model aliphatic and alicyclic carboxylic acids (surrogates 1-4) were studied using negative ion electrospray mass spectrometry (ESI-MS) in the presence and absence of alpha-, beta-, and gamma-cyclodextrin. Molecular ions were detected corresponding to the parent carboxylic acids and complexed forms of the carboxylic acids; the latter corresponding to non-covalent inclusion complexes formed between carboxylic acid and cyclodextrin compounds (e.g., beta-CD, alpha-CD, and gamma-CD). The formation of 1:1 non-covalent inclusion cyclodextrin-carboxylic complexes and non-inclusion forms of the cellobiose-carboxylic acid compounds was also observed.Aqueous solutions of Syncrude-derived mixtures of aliphatic and alicyclic carboxylic acids (i.e. naphthenic acids; NAs) were similarly studied using ESI-MS, as outlined above. Molecular ions corresponding to the formation of CD-NAs inclusion complexes were observed whereas 1:1 non-inclusion forms of the cellobiose-NAs complexes were not detected. The ESI-MS results provide evidence for some measure of inclusion selectivity according to the 'size-fit' of the host and guest molecules (according to carbon number) and the hydrogen deficiency (z-series) of the naphthenic acid compounds. The relative abundances of the molecular ions of the CD-carboxylate anion adducts provide strong support for differing complex stability in aqueous solution. In general, the 1:1 complex stability according to hydrogen deficiency (z-series) of naphthenic acids may be attributed to the nature of the cavity size of the cyclodextrin host compounds and the relative lipophilicity of the guest.

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“…This is because phenol cannot form stable inclusion complexes with CDs, as the single ring of phenol can enter the CDs' cavities freely, so that the fluorescence changes little. 26 In contrast, the fluorescence intensities of the inclusion complexes between BPA and CDs show great differences. HP-β-CD has the highest inclusion capability among these four CDs.…”

Section: Intermediate Analysis By Lc−msmentioning

confidence: 99%

Influences of Various Cyclodextrins on the Photodegradation of Phenol and Bisphenol A under UV Light

Zhou

Zhang

et al. 2015

Ind. Eng. Chem. Res.

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Recently, the removal of phenolic compounds has attracted great attention in wastewater treatment. In this work, the influences of various cyclodextrins (CDs) on the photodegradations of phenol and bisphenol A (BPA) under UV light were investigated systematically. The results show that the photodegradation of phenol displays no obvious differences in the presence or absence of CDs. In contrast, BPA photodegradation increases considerably in the presence of β-CD and its derivatives. Moreover, the catalytic effects of BPA differed among α-CD, β-CD, carboxymethyl-β-CD (CM-β-CD), and hydroxypropyl-β-CD (HP-β-CD), following the order β-CD ≈ HP-β-CD > CM-β-CD > α-CD. Specifically, over 99% of the BPA was degraded in the HP-β-CD and β-CD systems within 120 min. Additionally, six main intermediates of BPA in the presence of β-CD were confirmed, and the probable degradation pathway was proposed, which provides a useful platform for the application of CDs in the photodegradation of BPA.

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Formation, Structure, and Stability of α- and β-Cyclodextrin Inclusion Complexes of Phenol and Benzoic Acid Derivatives in Vacuo and in Water

Cited by 25 publications

References 37 publications

Interaction of naproxen with β-cyclodextrin and its derivatives/polymer: experimental and molecular modeling studies

Interaction of naproxen with β-cyclodextrin and its derivatives/polymer: experimental and molecular modeling studies

Electrospray ionization mass spectrometry studies of cyclodextrin‐carboxylate ion inclusion complexes

Influences of Various Cyclodextrins on the Photodegradation of Phenol and Bisphenol A under UV Light

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