Intrinsic Properties of α-Cyclodextrin Complexes with Benzoate Derivatives in the Gas Phase: An Experimental and Theoretical Study

Li, Zhongshu; Couzijn, Erik P. A.; Zhang, Xiangyang

doi:10.1021/jp210329a

Cited by 34 publications

(29 citation statements)

References 70 publications

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“…Other references suggest that the complementarity of the cavity size is also an important factor for the complexation. Mechanism studies for CD complexes in the gas phase have been performed using a combination of the mass spectrometric methods, namely, gas chromatography–mass spectrometry (GC–MS), ion mobility mass spectrometry (IMS–MS), infrared multiphoton dissociation (IRMPD) spectroscopy, and theoretical calculations involving various combinations of molecular dynamics (MD), semi-empirical, and density functional theory (DFT) methods [ 2 , 26 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 ]. Recently, structural analysis was conducted using action–FRET (Fluorescence Resonance Energy Transfer), a gas phase version of FRET in which chromophore-tagged β-cyclodextrin and amyloid-β fragment peptides were utilized [ 61 ].…”

Section: Introductionmentioning

confidence: 99%

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Lee

2020

Molecules

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Cyclodextrins (CDs) have drawn a lot of attention from the scientific communities as a model system for host–guest chemistry and also due to its variety of applications in the pharmaceutical, cosmetic, food, textile, separation science, and essential oil industries. The formation of the inclusion complexes enables these applications in the condensed phases, which have been confirmed by nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and other methodologies. The advent of soft ionization techniques that can transfer the solution-phase noncovalent complexes to the gas phase has allowed for extensive examination of these complexes and provides valuable insight into the principles governing the formation of gaseous noncovalent complexes. As for the CDs’ host–guest chemistry in the gas phase, there has been a controversial issue as to whether noncovalent complexes are inclusion conformers reflecting the solution-phase structure of the complex or not. In this review, the basic principles governing CD’s host–guest complex formation will be described. Applications and structures of CDs in the condensed phases will also be presented. More importantly, the experimental and theoretical evidence supporting the two opposing views for the CD–guest structures in the gas phase will be intensively reviewed. These include data obtained via mass spectrometry, ion mobility measurements, infrared multiphoton dissociation (IRMPD) spectroscopy, and density functional theory (DFT) calculations.

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Section: Introductionmentioning

confidence: 99%

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Lee

2020

Molecules

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“…[12] More recent studies have employed amino acids fragmentation mass spectrometry to investigate cyclodextrin complexes with small organic molecules. [13][14][15] A number of computational studies have served as support to the experimental investigations, leading to the general picture that isolated native cyclodextrins adopt symmetric conformations with extensive hydrogen bonding networks in their primary and secondary hydroxyl rims. [15][16][17][18][19][20][21][22][23] The coordination of a guest with the cyclodextrin must then compensate for the disruption of such a set of intramolecular hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

Cations in a Molecular Funnel: Vibrational Spectroscopy of Isolated Cyclodextrin Complexes with Alkali Metals

et al. 2012

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The benchmark inclusion complexes formed by α-cyclodextrin (αCD) with alkali-metal cations are investigated under isolated conditions in the gas phase. The relative αCD-M(+) (M=Li(+), Na(+), K(+), Cs(+)) binding affinities and the structure of the complexes are determined from a combination of mass spectrometry, infrared action spectroscopy and quantum chemical computations. Solvent-free laser desorption measurements reveal a trend of decreasing stability of the isolated complexes with increasing size of the cation guest. The experimental infrared spectra are qualitatively similar for the complexes with the four cations investigated, and are consistent with the binding of the cation within the primary face of the cyclodextrin, as predicted by the quantum computations (B3LYP/6-31+G*). The inclusion of the quantum-chemical cation disrupts the C(6) symmetry of the free cyclodextrin to provide the optimum coordination of the cations with the -CH(2)OH groups in C(1), C(2) or C(3) symmetry arrangements that are determined by the size of the cation.

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“…[2] They have hydrophilic exterior and hydrophobic internal cavity; thus, many molecules can be embraced in their cavities. [3,4] The wider upper rim of cavity is surrounded by the secondary hydroxyl groups, while the narrower one lines with the primary hydroxyl groups. [5] This hydroxyl groups can provide additional hydrogen bonds with guests.…”

Section: Introductionmentioning

confidence: 99%

DFT study the interaction of β‐cyclodextrin with benzyl azide and phenyl acetylene in synthesis of 1,2,3‐triazoles

Wan

Wang

Liu

2014

J of Physical Organic Chem

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The phenyl acetylene and benzyl azide cycloaddition reaction in water in the presence of β‐cyclodextrin (β‐CD) as a phase transfer catalyst (PTC) can get a better yield in a shorter time. The interaction between β‐CD and phenyl acetylene or benzyl azide plays an important role in this reaction. This paper studies the complexes of β‐CD with phenyl acetylene and benzyl azide using density functional theory (DFT) method. In order to find out the orientations of guests in the cavity of β‐CD, binding energy and deformation energy are investigated, and the calculated results are confirmed by 1H nuclear magnetic resonance (1HNMR). The data from single point energy indicate that the inclusion complexes can improve the solubilities of phenyl acetylene and benzyl azide in water. The 13C and 15N spectra show that the most obvious variation concentrates on C6 and C8 of phenyl acetylene and N15 of benzyl azide in complexes. Mulliken charge and frontier orbital are employed for revealing the charge distribution. The effect of β‐CD is discussed in terms of the calculated parameters. Copyright © 2014 John Wiley & Sons, Ltd.

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Intrinsic Properties of α-Cyclodextrin Complexes with Benzoate Derivatives in the Gas Phase: An Experimental and Theoretical Study

Cited by 34 publications

References 70 publications

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Cations in a Molecular Funnel: Vibrational Spectroscopy of Isolated Cyclodextrin Complexes with Alkali Metals

DFT study the interaction of β‐cyclodextrin with benzyl azide and phenyl acetylene in synthesis of 1,2,3‐triazoles

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