Contrasting structure-property relationships in amorphous, hierarchical and microporous aluminophosphate catalysts for Claisen-Schmidt condensation reactions

Annath, Hamza; Manayil, Jinesh C.; Thompson, Jillian M.; Marr, Andrew C.; Raja, Robert

doi:10.1016/j.apcata.2021.118376

Cited by 6 publications

(8 citation statements)

References 48 publications

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“…Considering the significance of this synthesis strategy, several catalysts with certain desirable characteristics have been developed to date. − Even today, extensive research is being performed to improve the existing methods. In 2016, Yu et al reported using Ca(OH) 2 for the condensation of aldehydes and methyl ketones.…”

Section: Resultsmentioning

confidence: 99%

“…Since then, different synthetic methods have been developed by changing the catalyst, solvent system, or both. Some of the most efficient catalysts used for this transformation are metal- or metal oxide-based catalysts, acid catalysts, base catalysts, , nanocatalysts, etc. However, their use has several drawbacks, such as toxicity or the requirement of harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of α,β-Unsaturated Ketones in Water: The Claisen–Schmidt Condensation Revisited

Choudhury

Mahapatra

Sahu

et al. 2022

ACS Sustainable Chem. Eng.

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Carrying out organic synthesis in an aqueous medium is always challenging. Herein, we present a highly efficient method for the synthesis of α,β-unsaturated ketones in water through the Claisen−Schmidt condensation by using a green catalyst, choline hydroxide (ChOH). The products were isolated without any chromatographic separation technique. The catalyst shows high substrate tolerance and works well with electrondonating and electron-withdrawing substituted aromatic aldehydes. Not only is the catalyst metal-free and nontoxic, but it also offers the advantage of forming strong hydrogen bonds with the transition state and intermediates, facilitating the reaction and enhancing the product yield. A variety of substrate scopes has been explored. The catalysis happens at 50 °C in water which is the significant finding of this study. The reaction mechanism of this hydrogen-bond-mediated catalysis was thoroughly investigated with density functional theory (DFT). The plausible reaction pathway was proposed based on the energetics of the reactants, intermediates, transition states, and product. Further, quantum theory of atoms in molecules (QTAIM) and noncovalent interactions (NCI) index analyses were done to demonstrate the effects of strong hydrogen bonds in the crucial steps of the reaction pathway. The obtained results correlate well with our hypothesis and validate our proposed mechanism, suggesting that the hydrogen-bond-mediated catalysis needs special attention in carrying out organic synthesis in water.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of α,β-Unsaturated Ketones in Water: The Claisen–Schmidt Condensation Revisited

Choudhury

Mahapatra

Sahu

et al. 2022

ACS Sustainable Chem. Eng.

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“…Reactive hydrogens from the basic structure of chalcones determine the possibility of these compounds being structurally modified in order to obtain a large number of derivatives [ 89 ]. Chalcones are precursors for many heterocyclic compounds such as cyanopyridines, 2-pyrazolines, pyrazoles, isoxazoles, pyrimidine-2-ones, flavanones and flavones and so forth [ 90 , 91 ]. Data from literature indicate that molecules with a 1,3-diaryl-2-propen-1-one residue have numerous biological activities and, for this reason, are of particular pharmacological importance [ 92 , 93 ].…”

Section: Flavonoidsmentioning

confidence: 99%

Two Important Anticancer Mechanisms of Natural and Synthetic Chalcones

Constantinescu

Mihis

2022

IJMS

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ATP-binding cassette subfamily G and tubulin pharmacological mechanisms decrease the effectiveness of anticancer drugs by modulating drug absorption and by creating tubulin assembly through polymerization. A series of natural and synthetic chalcones have been reported to have very good anticancer activity, with a half-maximal inhibitory concentration lower than 1 µM. By modulation, it is observed in case of the first mechanism that methoxy substituents on the aromatic cycle of acetophenone residue and substitution of phenyl nucleus by a heterocycle and by methoxy or hydroxyl groups have a positive impact. To inhibit tubulin, compounds bind to colchicine binding site. Presence of methoxy groups, amino groups or heterocyclic substituents increase activity.

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“…[21] Indeed, the performance of amorphous based devices in catalysis, solar energy generation, and electronics is highly dependent on their interfaces. [22][23][24] To achieve an amorphous surface, oftentimes a melt-quench bulk structure is cleaved via optimization with a large vacuum placed in the direction orthogonal to the surface. [10,[25][26][27] However, the suitability of this approach for generating amorphous surfaces has recently been called into question.…”

Section: Introductionmentioning

confidence: 99%

“…[ 21 ] Indeed, the performance of amorphous based devices in catalysis, solar energy generation, and electronics is highly dependent on their interfaces. [ 22–24 ]…”

Section: Introductionmentioning

confidence: 99%

Predicting Electronic Structure of Realistic Amorphous Surfaces

Repa

Fredin

2023

Advcd Theory and Sims

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Amorphous materials underlie the functionality of many devices in photocatalysis, electronics, and other technological applications. The performance of such devices is largely altered by the interfacial characteristics of the material motivating better understanding of their structure function relationships. However, open questions remain about how to generate atomistic representations of amorphous surfaces that are realistic while being amenable to computational study using electronic structure methods. Here, model parameters are explored to generate accurate amorphous surface models using prototypical amorphous titanium dioxide and a melt‐quench approach. In particular, non‐standard model considerations such as minimum sample size, unit cell size, and quench conditions are varied to efficiently explore amorphous structural space. The results indicate different modeling parameters have a substantial effect on surface morphology and electronic structure that significantly alters the interpretations gained by computational study of amorphous interfaces. Critically, it is shown that the structural motifs that contribute to such differences are not detectable by short range structural analysis that has traditionally been used to assess the quality of melt‐quench derived amorphous structures.

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Contrasting structure-property relationships in amorphous, hierarchical and microporous aluminophosphate catalysts for Claisen-Schmidt condensation reactions

Cited by 6 publications

References 48 publications

Synthesis of α,β-Unsaturated Ketones in Water: The Claisen–Schmidt Condensation Revisited

Synthesis of α,β-Unsaturated Ketones in Water: The Claisen–Schmidt Condensation Revisited

Two Important Anticancer Mechanisms of Natural and Synthetic Chalcones

Predicting Electronic Structure of Realistic Amorphous Surfaces

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