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April 29, 2026Acta Chimica Slovaca0 citationsOpen Access

Synthesis, molecular and electronic properties, and crystal structure of two novel potent perfluorophenylhydrazone derivatives, 1-((5-nitrothiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, and 1-((5-nitrofuran-2-yl)methylene)-2-(perfluorophenyl) hydrazine

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JSJ. SivýSlovak University of Technology in BratislavaDVDaniel VéghSlovak University of Technology in BratislavaDBDušan BortňákSlovak University of Technology in Bratislava

Key Points

  • The research presents two new perfluorophenylhydrazone derivatives and evaluates their properties and structures for AD therapy.
  • Synthesis and characterization of compounds I and II using elemental and spectroscopic analysis (1H-NMR).
  • Crystal structures determined via single-crystal X-ray diffraction with monoclinic space groups.
  • Non-covalent interactions analyzed, including hydrogen bonding and π-ring interactions.
  • Both compounds were synthesized successfully with confirmed stereochemistry.
  • Compound I crystallizes as a dimer while compound II crystallizes as a racemate.
  • Diverse non-covalent interactions were observed in the crystal structures, including hydrogen bonding.

Abstract

Abstract Two novel potent perfluorophenylhydrazone derivatives, 1-((5-nitrothiophen-2-yl)methylene)-2-(per- fluorophenyl)hydrazine, ( I ), and 1-((5-nitrofuran-2-yl)methylene)-2-(perfluorophenyl) hydrazine, ( II ), are introduced, with suggested improvement by further design. Their multitarget structures and features have been combined to create potential AD therapeutics. Crystals ( I ) and ( II ) are molecules with two rings and a hydrazone part at the centre of the molecule. They were synthesised and characterised using elemental and spectroscopic ( 1 H-NMR) analyses and their crystal structures were determined using the single-crystal X-ray diffraction method. The structures crystallise in the monoclinic space group with Z = 2 and Z = 4 molecules per unit cell. Compound ( I ) crystallises as a dimer in the non-centrosymmetric space group, while compound ( II ) crystallises as a racemate in the centrosymmetric space group. The “absolute configuration and conformation for bond values” were not derived from anomalous dispersion (rmad). The crystal structures reveal diverse non-covalent interactions such as intra- and inter-hydrogen bonding, π-ring — π-ring, C—H — π-ring interactions. The expected stereochemistry of hydrazone atoms C7, N2, and N1 was confirmed for compounds ( I ) and ( II ). Both molecules possess a “boat conformation” resembling a 6-membered ring. Results of the single crystal studies were reproduced using the Hirshfeld surface analysis, Gaussian software, and QTAIM contour mapping.

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Cite This Study

Sivý et al. (2026) studied this question.

synapsesocial.com/papers/69f154c0879cb923c4944f7ahttps://doi.org/10.2478/acs-2026-0002
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