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η3-allyl-Pd(II) complexes of 2-, 3- and 4-pyridylmethyl-coumarin esters

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Abstract

A series of 2-, 3- and 4-pyridylmethyl-coumarin esters ligands (1–3) and their η3-allyl palladium complexes (1-Pd–3-Pd) have been designed, synthetized, and characterized. NMR analysis of compounds 1-Pd–3-Pd indicated the presence of the allyl fragment. The molecular structures of 2, 3 and 1-Pd were determined by X-ray crystallographic analysis. The molecular structure of 1-Pd reveals that coumarin ligand (2) is coordinated to the palladium center via a monodentate fashion through the nitrogen atom of the pyridinyl fragment while, the allyl group is binding via a η3 fashion in an overall square-planar geometry completed with a chloride atom. The crystal packing is stabilized by a variety of weak intermolecular conventional and non-conventional interactions involving C–H–O/N hydrogen bonds, π–π and C–H–π interactions, which have been analyzed by Hirshfeld surface and non-covalent interactions analysis. The intermolecular interaction energies were explored using an energy framework analysis, which revealed that π–π and C–H–π interactions serve as the primary building blocks in these crystal packing.

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Acknowledgements

This research was supported by the Universidad Autónoma del Estado de Hidalgo (Grant: UAEH-DIDI-DI-ICBI-QUI-22-004) to SG-M.

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Authors and Affiliations

  1. Área Académica de Química, Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Hidalgo, km. 4.5 Carretera Pachuca-Tulancingo, Ciudad del Conocimiento, 42184, Mineral de la Reforma, Hidalgo, Mexico

    Simplicio González-Montiel, René Velázquez-Jiménez, Raúl Segovia-Pérez, Willyfredo Fragoso-Soto, Noemí Andrade-López, Verónica Salazar-Pereda & Julián Cruz-Borbolla

  2. Parque Científico y Tecnológico, Universidad Autónoma del Estado de Hidalgo, Blvd. Ciudad del Conocimiento, Mza. 15 Lote 2, 42162, Santa Catarina, San Agustín Tlaxiaca, Hidalgo, Mexico

    René Velázquez-Jiménez

  3. Centro Conjunto de Investigación en Química Sustentable, UAEM-UNAM, Carretera Toluca-Atlacomulco km. 14.5, 50200, Toluca, Estado de Mexico, Mexico

    Diego Martínez-Otero

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  1. Simplicio González-Montiel
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Contributions

SG-M contributed to the validation, formal analysis, data curation, methodology, supervision-lead, writing—review and editing, visualization, conceptualization and resources; RV-J was involved in the validation, formal analysis, data curation and methodology; RS-P assisted in the validation, formal analysis and data curation; WF-S contributed to the methodology and supporting; DM-O was involved in the formal analysis and data curation; NA-L contributed to supporting and formal analysis; VS-P was involved in supporting and formal analysis; JC-B contributed to the validation, formal analysis and data curation. All authors reviewed the manuscript.

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Correspondence to Simplicio González-Montiel.

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González-Montiel, S., Velázquez-Jiménez, R., Segovia-Pérez, R. et al. η3-allyl-Pd(II) complexes of 2-, 3- and 4-pyridylmethyl-coumarin esters. Transit Met Chem 48, 21–36 (2023). https://doi.org/10.1007/s11243-022-00518-3

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