Reversal in Solvatochromism, enol-imine/keto-amine Tautomerism and (E)-(Z) Photoisomerizations in a Benzylidene Aniline Schiff Base Derivative in Different Solvents

Molecules, Год журнала: 2025, Номер 30(3), С. 745 - 745

Опубликована: Фев. 6, 2025

A novel Schiff base, (E)-4-acetyl-N-(4-hydroxy-3-methoxybenzylidene)aniline (abbreviated as ANHMA), was synthesized and characterized using infrared 1H- 13C-NMR spectroscopies. Optical properties in different solvents were evaluated UV-vis absorption spectroscopy. The compound is shown to exhibit both positive negative solvatochromism with reversal occurring for ET(30)~45 (e.g., DMSO). solvatochromic behavior of the found be strongly dependent on hydrogen bond abilities polarizability solvent, observed being explained by change dominant solvent effects non-polar polar–aprotic (H-bond acceptor ability polarizability) compared polar–protic donor ability), according developed Catalán multiparametric model. In all freshly prepared solutions studied, (E)-enol-imine tautomer predominate over keto-amine tautomeric forms, latter increasing their populations time presence H-bond donor/acceptor species. Irradiation ANHMA UV light (λ ≥ 311 nm) also investigated several follow a general pattern, conversion into forms solvent-mediated enol-imine/keto-amine tautomerism, (Z)→(E) C=C isomerization between keto-imine forms. experimental results received support from an extensive series calculations structure spectra relevant tautomeric/isomeric performed at DFT(B3LYP)/6-311++G(d,p) level approximation (including time-dependent DFT consideration).

Язык: Английский

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Therapeutic and Structural Insights into Selenium Bearing Inflammatory Inhibitors and DNA Intercalators

Journal of Molecular Structure, Год журнала: 2025, Номер unknown, С. 142790 - 142790

Опубликована: Май 1, 2025

Язык: Английский

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Synthesis and characterization of 3,5-bis((2-hydroxybenzylidene)amino)-N-(2-hydroxyphenyl)benzamide and Zn(II) complex: Investigation of chromic, fluorescence and DPPH radical scavenging behaviours

Inorganica Chimica Acta, Год журнала: 2024, Номер unknown, С. 122410 - 122410

Опубликована: Окт. 1, 2024

Язык: Английский

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