Synthesis and characterization of novel conformers of (E)‐2‐(3‐nitro‐H‐imidazo[1,2‐a]pyridin‐2‐ylthio)‐N′‐benzylideneacetohydrazide derivatives

Evrard, Ablo; Coulibaly, Souleymane; Coulibali, Siomenan; Signo, Kouassi; Achi, Patrick‐Armand; Giraud, Nicolas; Bertho, Gildas

doi:10.1002/mrc.5308

“…9 The electronic conjugation intrinsic to these molecules can significantly influence charge transport properties, offering opportunities for exploitation in the development of optoelectronic devices such as organic light-emitting diodes (OLEDs), 10 and organic fieldeffect transistors (OFETs). 11 Building upon our prior studies, 12,13 which consistently established the stable (E) conformation of N-acylhydrazones in various solvents, particularly the prevalence of the syn conformation in solvents like DMSO-d6, we identified conditions favoring the anti conformation, including less polar solvents (e.g., CDCl3), intramolecular hydrogen bonding, or steric hindrance. The persistent dominance of the syn conformation, where crucial substituents adopt specific spatial orientations, suggests a structural regularity with promising implications for the design of novel molecules tailored for specific purposes.…”

Section: Introductionmentioning

confidence: 98%

Unveiling the Synthesis, Spectral Characterizations, and Electrochemical Potential of Novel (E)-Furan-2-yl Acrylohydrazides: An Exploration in Molecular Design

Penayori Marie-Aimée,

Coulibaly,

N'Dri

et al. 2024

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In this study, we present the synthesis of novel derivatives of 3-furan-2-yl acrylohydrazide using a meticulous three-step reaction sequence. The synthesis ends up in the condensation of (E)-3-(furan-2-yl) acrylohydrazine (3) with diverse benzaldehyde and acetophenone derivatives. Comprehensive characterization of the synthesized compounds was achieved through 1D NMR spectroscopic analyses (1H and 13C NMR), 2D NMR spectroscopy (HSQC, NOESY), and high-resolution mass spectrometry (HRMS). The investigation of 1H NMR data at room temperature in deuterated dimethyl sulfoxide (DMSO-d6) unveiled the existence of (E)-3-(furan-2-yl) acrylohydrazide derivatives (4a-h) in a conformational equilibrium, manifesting as a mixture of synperiplanar E (sp E) and antiperiplanar E (ap E), or synperiplanar Z (sp Z) and antiperiplanar Z (ap Z). Notably, compounds 4a and 4b predominantly adopted the sp E conformer (Ec=c sp EC=N), while compounds 4c and 4d favored the antiperiplanar conformation. For the remaining compounds (4e-h), both conformers were nearly equimolar, with a marginal preference for the anti over the syn conformer. Interestingly, compounds 4f and 4h exhibited a prevalence of the apZ conformer (Ec=c ap ZC=N), while compound 4e featured the apE conformer (Ec=c ap EC=N). UV-visible absorption spectra for the N-acylhydrazones (4a-h) indicated absorption within the 570-635 nm range. Furthermore, cyclic voltammetry results demonstrated the capacity of the synthesized (E)-3-(furan-2-yl) acrylohydrazide derivatives (4a-h) to undergo quasi-reversible oxidation and reduction processes on a platinum electrode. These findings contribute valuable insights into the conformational dynamics and electrochemical behavior of this class of compounds, holding significance for applications in diverse scientific and technological domains.

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Theoretical Investigation on the Stability and Reactivity of Imidazo [1,2-a] Pyridine N-Acylhydrazone Derivatives Using Density Functional Theory

Etienne,

Kassoum,

Ouehi

et al. 2024

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The reactivity and stability of seventeen (17) imidazo [1,2-a]pyridine N-acylhydrazone derivatives were investigated using density functional theory at the B3LYP/6-31+ G (d, p) level. Analysis of the molecular electrostatic potential (MEP) and determination of the dual descriptor revealed that in most cases, the nitrogen atoms of the 6-πelectron conjugation, the oxygen, and the sulfur atom are nucleophilic site. Chemical reactivity of the compounds was assessed through analysis of frontier molecular orbitals (HOMO and LUMO), energy gap ( Δ ), chemical hardness (η), and the softness (S).Consequently, the compound 9e exhibited the lowest reactivity, least electron donating, and the highest stability. This comprehensive study offers valuable insights into the chemical behavior of these derivatives, crucial for further exploration and potential applications.

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Unveiling the synthesis and spectral characterizations of novel (E)-furan-2-yl acrylohydrazides: an exploration in molecular design

Coulibaly,

Ablo

et al. 2024

PeerJ Organic Chemistry

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In this study, we present the synthesis of novel derivatives of 3-furan-2-yl acrylohydrazide using a meticulous three-step reaction sequence. The synthesis ends up in the condensation of (E)-3-(furan-2-yl) acrylohydrazide (3) with diverse benzaldehyde and acetophenone derivatives. Comprehensive characterization of the synthesized compounds was achieved through 1D nuclear magnetic resonance spectroscopic analyses (1H and 13C NMR), 2D nuclear magnetic resonance spectroscopy (HSQC, NOESY), and high-resolution mass spectrometry (HRMS). The investigation of 1H NMR data at room temperature in deuterated dimethyl sulfoxide (DMSO-d6 ) unveiled the existence of (E)-3-(furan-2-yl) acrylohydrazide derivatives (4a–h) in a conformational equilibrium, manifesting as a mixture of synperiplanar E (sp E) and antiperiplanar E (ap E), Notably, compounds 4a and 4b predominantly adopted the sp E conformer (Ec=c sp EC=N), while the remaining compounds (4c–h), favored the antiperiplanar conformation (Ec=c ap EC=N) even if for the 4g compound it was challenging to determine the EC=N conformer. These findings contribute valuable insights into the conformational dynamics of this class of compounds, holding significance for applications in diverse scientific domains.

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Synthesis and characterization of novel conformers of (E)‐2‐(3‐nitro‐H‐imidazo[1,2‐a]pyridin‐2‐ylthio)‐N′‐benzylideneacetohydrazide derivatives

Cited by 3 publications

References 26 publications

Unveiling the Synthesis, Spectral Characterizations, and Electrochemical Potential of Novel (E)-Furan-2-yl Acrylohydrazides: An Exploration in Molecular Design

Unveiling the Synthesis, Spectral Characterizations, and Electrochemical Potential of Novel (E)-Furan-2-yl Acrylohydrazides: An Exploration in Molecular Design

Theoretical Investigation on the Stability and Reactivity of Imidazo [1,2-a] Pyridine <i>N</i>-<i>Acylhydrazone</i> Derivatives Using Density Functional Theory

Unveiling the synthesis and spectral characterizations of novel (E)-furan-2-yl acrylohydrazides: an exploration in molecular design

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