Brønsted acid-catalyzed chlorination of aromatic carboxylic acids

Yu, Zhiqun; Yao, Hongmiao; Xu, Qilin; Liu, Jiming; Le, Xingmao; Ren, Minna

doi:10.1080/10426507.2021.1903008

Cited by 3 publications

(1 citation statement)

References 22 publications

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“…Synthesis of the compounds was accomplished following modified procedures from previous reports. , In brief, 3-nitrobenzoyl chloride (1 equiv), the appropriate alcohol (2 equiv), and pyridine (2 equiv) were dissolved in dichloromethane. The reaction flask was sealed, and the contents were magnetically stirred at room temperature overnight.…”

Section: Methodsmentioning

confidence: 99%

Discerning the Impact of Noncovalent Interactions via Simulated Crystal Growth: A Structural Study of Aromatic Esters

Boucher,

Bellia,

Howarth

et al. 2024

Crystal Growth & Design

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The synthesis and structural characterization of seven systematically varied aromatic esters are reported. The compounds are analyzed using single-crystal X-ray diffraction, dynamic scanning calorimetry, and variabletemperature viscometry. The state of the compounds, i.e., liquid and solid, is controlled, in part, via sterics of the ester functionalities which influence the presence of specific noncovalent interactions in the solid state. Two distinct conformational polymorphs are observed in the solid state. To rationalize the formation of the conformational polymorphs, the intermolecular forces of the crystalline structures were studied via Hirshfeld surface analysis, leading to the conclusion that the unique geometries are controlled by a combination of halogen contacts, π interactions, and interactions involving the nitro group on the aromatic rings. These conclusions are further examined via computational studies of the conformers, analysis of packing efficiency, and assessment of the structure of the energy frameworks for the crystalline solids. Finally, the information derived from the analysis of the interactions is used to simulate the growth of the crystals, helping to rationalize the conclusions about which interactions are responsible for the phase behavior of the compounds.

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Section: Methodsmentioning

confidence: 99%

Discerning the Impact of Noncovalent Interactions via Simulated Crystal Growth: A Structural Study of Aromatic Esters

Boucher,

Bellia,

Howarth

et al. 2024

Crystal Growth & Design

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Novel approach of thionyl chloride detection and disposal using a benzimidazole-based derivative: perspectives and proposals

Kabaňová,

Tokárová

2024

Int. J. Environ. Sci. Technol.

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Benzimidazoles are important heterocyclic compounds that exhibit a wide range of pharmacological and biological properties. Among all, sensitivity to Lewis acids provide a possibility to act as a fluorescent detectors for senzing the cathions, radicals, highly reactive low-molecular species with hazardous effects to environment and human health. Herein, we present the design and synthesis of N-((1H-benzo[d]imidazol-2-yl)methyl)cinnamamide (I) for the detection of readily reactive thionyl chloride (SOCl2). Treatment of SOCl2 with a novel benzimidazole-based compound I is accompanied by immediate color change. Although the process is irreversible the change noticeable by eye is profitable for a simple and rapid protection against the SOCl2 exposure at amounts harmful for surroundings and body. In the context of environmental issue, the chemical reaction between the detector I and thionyl chloride is beneficial for the safe waste disposal. Thionyl chloride is recaptured in the structure of I throughout the reaction leading to a formation of stable compound II. Incorporation of residual traces of SOCl2 into the structure of organic-type detector I represents effective route to achieve non-reactive and non-damaging derivatives. Accordingly, the organic non-liquid waste is subsequently stored and disposed in a safe manner.

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Catalytic Asymmetric Conjugate Addition of 2-Methyl-3,5-dinitrobenzoates to Unsaturated Ketones

Chen

et al. 2022

J. Org. Chem.

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Asymmetric catalytic vinylogous Michael addition of 2-methyl-3,5-dinitrobenzoates to unsaturated ketones catalyzed by chiral rhodium catalysts has been established. This strategy allowed the synthesis of a variety of optically pure compounds containing imidazole and 3,5-dinitrobenzene skeletons in 64−98% yields with 88−98% ee. The developed reaction not only represents highly asymmetric catalytic enantioselective vinylogous Michael addition employing 2-methyl-3,5-dinitrobenzoates as a building block but also enriches the chemistry of catalytic asymmetric vinylogous Michael addition of 2-methyl-3,5-dinitrobenzoates. Furthermore, the protocol showed obvious advantages in reaction activity and enantioselectivity. When the chiral rhodium catalyst was reduced to 0.06 mol %, the gram-level reaction was still achieved to provide the desired product with 95% ee.

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Brønsted acid-catalyzed chlorination of aromatic carboxylic acids

Cited by 3 publications

References 22 publications

Discerning the Impact of Noncovalent Interactions via Simulated Crystal Growth: A Structural Study of Aromatic Esters

Discerning the Impact of Noncovalent Interactions via Simulated Crystal Growth: A Structural Study of Aromatic Esters

Novel approach of thionyl chloride detection and disposal using a benzimidazole-based derivative: perspectives and proposals

Catalytic Asymmetric Conjugate Addition of 2-Methyl-3,5-dinitrobenzoates to Unsaturated Ketones

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