The interplay between hydrogen and halogen bonding: substituent effects and their role in the hydrogen bond enhanced halogen bond

Berryman, Orion B.; Sun, Jiyu; Decato, Daniel A.; John, Eric A.; Bryantsev, Vyacheslav S.

doi:10.1039/d3sc02348f

Cited by 8 publications

(3 citation statements)

References 76 publications

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“…It is worth noting that compared with the catalyst E-ET, E-SO performs more sensitively for alcohol oxidation with different substituent groups. It is possibly due to the different substituent groups (including electron-drawing and electron-donating groups) affecting the environment of the H atom, which results in hydrogen bond differences. − In addition, to verify the advantage of the encapsulated structure, we compared the oxidation effects of the supported catalysts and encapsulated catalysts. The encapsulated catalysts showed more favorable performance in alcohol oxidation, especially with the SO group modified (Table S4).…”

Section: Resultsmentioning

confidence: 99%

Surface-Modified S═O Microenvironment Boosts Catalyzed Oxidation of Alcohol via Hydrogen Bond Interactions

Feng,

Shi,

Zhu

et al. 2024

ACS Catal.

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Enzymes have unique structures, with various amino acid residues encapsulating metal active sites. Their high performance is mainly achieved via weak interactions between the functional groups and the substrate. Inspired by the enzyme structure, we designed an encapsulated catalyst (E-S�O) wherein AuPd nanoparticles were encapsulated by porous organic frameworks (POFs) modified with S�O groups. The alcohol reaction rate of E-S�O increased 2-fold compared with the control catalyst without S�O groups. The hydrogen bond was formed between alcohol and S�O groups, which was confirmed via 1 H NMR and inverse-phase gas chromatography (IGC) tests. Further insight including adsorption isotherm, in situ diffuse reflective infrared Fourier transform spectroscopy (DRIFTS), and the kinetics data confirmed the hydrogen bond could account for the rate enhancement. The proposed catalyst preparation strategy through precise microenvironment control via hydrogen bonds with substrates paves a new way for high-performance catalyst design.

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Section: Resultsmentioning

confidence: 99%

Surface-Modified S═O Microenvironment Boosts Catalyzed Oxidation of Alcohol via Hydrogen Bond Interactions

Feng,

Shi,

Zhu

et al. 2024

ACS Catal.

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“…Subsequently, we also developed the hydrogen bond enhanced halogen bond (HBeXB) which has allowed us to preorganize structure and strengthen XBs by employing complementary intramolecular HBs to the electron-rich belt of XB donors. 54−56 The HBeXB can increase binding by 50fold 57 and our lab and others have used the HBeXB to improve the function of organocatalysts. 58−60 Ho et al have also demonstrated that the HBeXB stabilizes protein folding and enhances the function of a T4 lysozyme derivative.…”

Section: ■ Introductionmentioning

confidence: 99%

Taming Molecular Folding: Anion-Templated Foldamers with Tunable Quaternary Structures

John,

Riel,

Wieske

et al. 2024

J. Am. Chem. Soc.

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Higher-order foldamers represent a unique class of supramolecules at the forefront of molecular design. Herein we control quaternary folding using a novel approach that combines halogen bonding (XBing) and hydrogen bonding (HBing). We present the first anion-templated double helices induced by halogen bonds (XBs) and stabilized by "hydrogen bond enhanced halogen bonds" (HBeXBs). Our findings demonstrate that the number and orientation of hydrogen bond (HB) and XB donors significantly affect the quaternary structure and guest selectivity of two similar oligomers. This research offers new design elements to engineer foldamers and tailor their quaternary structure for specific guest binding.

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“…Hydrogen bonding (HB), [1][2][3][4][5][6][7][8] halogen bonding (XB) [9][10][11][12][13][14] and chalcogen bonding (ChB), [15][16][17][18][19][20][21][22] three prominent non-covalent interactions that are weaker than covalent bonds, but can efficiently induce monomer aggregation, have been highly anticipated in self-assembly chemistry over the past two decades. Since the discovery of the double helical structure of DNA by Watson and Crick, 23 chemists have been drawn to design simple linear molecules that are able to form artificial helices.…”

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confidence: 99%

Multiple non-covalent-interaction-directed supramolecular double helices: the orthogonality of hydrogen, halogen and chalcogen bonding

Liu,

Zhang,

et al. 2024

Chem. Commun.

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The interplay between hydrogen and halogen bonding: substituent effects and their role in the hydrogen bond enhanced halogen bond

Abstract: The Hydrogen Bond Enhanced Halogen Bond (HBeXB) has recently been used to effectively improve anion binding, organocatalysis, and protein structure/function. In this study, we present the first systematic investigation of...

Cited by 8 publications

References 76 publications

Surface-Modified S═O Microenvironment Boosts Catalyzed Oxidation of Alcohol via Hydrogen Bond Interactions

Surface-Modified S═O Microenvironment Boosts Catalyzed Oxidation of Alcohol via Hydrogen Bond Interactions

Taming Molecular Folding: Anion-Templated Foldamers with Tunable Quaternary Structures

Multiple non-covalent-interaction-directed supramolecular double helices: the orthogonality of hydrogen, halogen and chalcogen bonding

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