Chitosan/La catalyzed synthesis of novel ferrocenated spiropyrrolizidines: Green synthesis, crystallographic, DFT and Hirshfeld surface studies

•Novel chitosan/La-catalysed ferrocenated spiropyrrolizidines were designed and synthesized.•Spectroscopy was used to determine structures, which were then correlated with a single crystal X-ray diffraction analysis.•DFT and Hirshfeld analysis were employed to optimize the compound's molecular...

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Published in:Journal of molecular structure 2025-02, Vol.1322, p.140240, Article 140240
Main Authors: Asad, Mohammad, Arshad, Muhammad Nadeem, Azum, Naved, Alzahrani, Khalid A., Marwani, Hadi M., Elhenawy, Ahmed A., Alam, Mohammad Mahboob, Nazreen, Syed, K, Snigdha, TN, Mohammed Musthafa
Format: Article
Language:English
Subjects:
Chitosan/La catalyst
DFT study
Ferrocenated spiropyrrolizidines
Green synthesis
Hirshfeld surface study
X-ray crystallography
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Summary:•Novel chitosan/La-catalysed ferrocenated spiropyrrolizidines were designed and synthesized.•Spectroscopy was used to determine structures, which were then correlated with a single crystal X-ray diffraction analysis.•DFT and Hirshfeld analysis were employed to optimize the compound's molecular structure. A novel polymeric catalytic system, utilizing chitosan-bounded lanthanum (chitosan/La), facilitated the formation of spiropyrrolizidine hybrids in higher yield. These hybrids were synthesized via one-pot three component 1,3-dipolar cycloaddition reaction involving ferrocenated chalcones, and azomethine ylides. The chemical structures were elucidated using various spectroscopic techniques and further confirmed via X-ray crystallography of a compound 3. Density functional theory (DFT) calculations executed followed by Gaussian 09 and GaussView 5.0 software provided insights into the optimal structure of molecular compounds. The computational analysis employed the 6–311G++ (d,p) higher-order basis set and the B3LYP method. Additionally, Hirshfeld surface analysis was utilized to predict crystallographic shapes, revealing van der Waals interaction contributing to crystal stabilization. [Display omitted]
ISSN:0022-2860
DOI:10.1016/j.molstruc.2024.140240