A review on oxime functionality: an ordinary functional group with significant impacts in supramolecular chemistry

Tarai, Arup; Nath, Bhaskar

doi:10.1039/d4cc01397b

Chem. Commun.

2024

DOI: 10.1039/d4cc01397b

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A review on oxime functionality: an ordinary functional group with significant impacts in supramolecular chemistry

Arup Tarai,

Bhaskar Nath

Abstract: This article explores the medicinal, agricultural, crystal engineering, analyte recognition, and coordination chemistry aspects of oxime derivatives to inspire researchers to develop novel oximes for future applications.

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Cited by 3 publications

References 183 publications

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Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Vara,

Thete,

Ghotekar

et al. 2024

Chemistry An Asian Journal

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A simple and efficient strategy for the synthesis of structurally diverse β,β‐diarylmethine substituted isoxazoline derivatives have been developed. This approach employs a manganese‐promoted oxidative cyclization coupled with a 1,6‐conjugate addition of unsaturated oximes to p‐quinone methides. The key features of this study include the formation of C‐O and C‐C bonds through intramolecular and intermolecular interactions, facilitated by in situ generated iminoxyl radicals. β,β‐diarylmethine substituted isoxazolines, bearing a wide range of functional groups, were isolated in high yields

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Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Vara,

Thete,

Ghotekar

et al. 2024

Chemistry An Asian Journal

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Exploring Polymorphism in Quinoline‐4‐Carbaldoxime: Experimental Validation and Computational Insights into Hydrogen Bonding and Structural Variations

Tarai,

Sutradhar

et al. 2024

ChemistrySelect

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This study identifies and characterizes a second polymorph (Poly‐II) of quinoline‐4‐carbaldoxime (HQ), isolated from an acetone‐acetonitrile mixture. Poly‐II was compared to the previously known Poly‐I using PXRD, DSC, IR, and Raman spectroscopy. Poly‐I forms a 1D supramolecular assembly, whereas Poly‐II exhibits a 2D assembly with additional hydrogen bonds. Hirshfeld surface analysis reveals the presence of different non‐covalent interactions in Poly‐I and Poly‐II, and atom‐in‐molecule (AIM) analysis identifies their strength. AIM analysis, along with Espinosa's relation, was used to calculate the strength of O─H···N and C─H···N interactions in Poly‐I and Poly‐II. The values are −30.0 and −6.17 kJ/mol for Poly‐I, whereas the values for Poly‐II are −36.18 and −3.66 kJ/mol. The plane wave periodic DFT calculations determined the lattice energies of Poly‐I and Poly‐II to be −1.52 and −1.53 eV, respectively, indicating that both polymorphs have comparable stability. The crystal parameters of Poly‐I and Poly‐II obtained from theoretical simulations and the experiment are comparable, indicating the similar stability of Poly‐I and Poly‐II. Computational simulations confirmed experimental data, showing both polymorphs have similar stability and melting points despite different unit cell volumes.

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A Review: Recent Advances in Chemistry and Applications of 2,4-Dihydroxybenzaldehyde Oxime and Its Transition Metal Complexes

Reema Chand,

Mohseen Ahmed,

Bibhesh K. Singh

2024

J. Adv. Chem. Sci.

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This review presents a comprehensive overview of the recent advances in the chemistry and applications of 2,4-dihydroxybenzaldehyde oxime (DHBO) and its transition metal complexes. DHBO, characterized by its unique hydroxyl and oxime functional groups, has gained significant attention due to its versatile reactivity and potential applications across various fields, including pharmaceuticals, catalysis, and environmental science. Recent synthetic methodologies, including microwave-assisted techniques and green chemistry approaches, have improved the efficiency and sustainability of DHBO production. The formation of transition metal complexes with DHBO has been a focal point of research, revealing enhanced catalytic properties and biological activities compared to the free ligand. These complexes have shown promise in organic synthesis, particularly in oxidation and reduction reactions, as well as in drug development, exhibiting antimicrobial and anticancer properties. Furthermore, the potential of DHBO and its metal complexes in environmental remediation, particularly in removing heavy metals and pollutants, underscores their significance in addressing contemporary environmental challenges. This review also provides current knowledge on the synthesis, characterization, and applications of DHBO and its transition metal complexes, highlighting their importance in both academic research and industrial applications. By elucidating the multifaceted roles of DHBO, this work aims to pave the way for future research and innovation in this promising area of study.

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A review on oxime functionality: an ordinary functional group with significant impacts in supramolecular chemistry

Abstract: This article explores the medicinal, agricultural, crystal engineering, analyte recognition, and coordination chemistry aspects of oxime derivatives to inspire researchers to develop novel oximes for future applications.

Cited by 3 publications

References 183 publications

Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Exploring Polymorphism in Quinoline‐4‐Carbaldoxime: Experimental Validation and Computational Insights into Hydrogen Bonding and Structural Variations

A Review: Recent Advances in Chemistry and Applications of 2,4-Dihydroxybenzaldehyde Oxime and Its Transition Metal Complexes

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