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Synthesis, crystal structure, Hirshfeld surface analysis, and DFT studies of 2-bromo-4,6-bis(dibromoacetyl)resorcinol

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Abstract

The synthesis and crystal structure of 2-bromo-4,6-bis(dibromoacetyl)resorcinol, I, was reported. In the title compound, I, crystalized in the triclinic crystal system with Pī space group. The two carbon and the oxygen atom of the acetyl groups (atoms C7, C8, O3, and C9, C10, O4) are nearly co-planar with the central phenyl ring. Intramolecular O–H···O, C–H···Br, and intermolecular C–H···Br/O interactions, two non-bonded contacts (Br5···Br3 and O4···C8) and π-π stacking interaction are stabilized the crystal packing of the title compound. Intermolecular interactions that exist in the title compound, I, are quantified with the aid of PIXEL and Hirshfeld surface (HS) analysis and the decomposed fingerprint (FP) plots. The FP plot reveals that the Br···Br contacts are comparably higher than the other contacts in the title crystal structure. Furthermore, the theoretical density functional theory (DFT) calculations were performed at the M062X/cc-PVTZ level of theory. The experimental geometry parameters of the title molecule are compared with the geometry of the optimized molecule in the gas phase. The chemical reactivity and charge transfer properties of the title compound were calculated from the HOMO and LUMO energy. In addition, the molecular electrostatic potential map was generated at their crystal structure geometry and quantitatively analyzed.

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Acknowledgements

The authors PV and MJP wish to express their gratitude to VIEP-BUAP (grant pv19-ID00375, and grant 00110-VIEP-202). Also, the authors thankfully acknowledge the computer resources and technical support provided by the Laboratorio Nacional de Supercómputo del Sureste de México. KL and MP wish to thank the Jamal Mohamed College management for providing the necessary facilities.

Funding

The authors PV and JP have received research support from VIEP-BUAP (grant pv19-ID00375, and grant 00110-VIEP-202).

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Authors and Affiliations

  1. Department of Chemistry, Jamal Mohamed College, (Autonomous and Affiliated to Bharathidasan University, India), Tiruchirappalli-620 020, Tamilnadu, India

    K. Loganathan, M. Purushothaman & P. Daniel Jebaraj

  2. Department of Chemistry, Srimad Andavan Arts and Science College, (Autonomous and Affiliated to Bharathidasan University, India), Tiruchirappalli-620 005, Tamilnadu, India

    A. Anandan & Perumal Venkatesan

  3. Department of Chemistry, Government Arts College, (Autonomous and Affiliated to Bharathidasan University, India), Tiruchirappalli-620 022, Tamilnadu, India

    K. Thanigaimani

  4. Unidad de Polímeros Y Electrónica Orgánica, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Val3-Ecocampus Valsequillo, Independencia O2 Sur 50, 72960, Puebla, San Pedro Zacachimalpa, Mexico

    M. Judith Percino

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Contributions

K. Loganathan: conceptualization, chemical synthesis, characterization; A. Anandan: conceptualization, investigation, crystal structure analysis, characterization, writing—original draft; M. Purushothaman: conceptualization, chemical synthesis, characterization, writing—review and editing; P. Daniel Jebaraj: chemical synthesis; K. Thanigaimani: data curation, review; M. Judith Percino: resources, data curation, writing—review and editing; P. Venkatesan: conceptualization, investigation, supervision, writing—original draft—review and editing.

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Correspondence to M. Purushothaman or Perumal Venkatesan.

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Authors PV and JP have research funding from VIEP-BUAP (grant pv19-ID00375, and grant 00110-VIEP-202), and other authors declare they have no financial interests.

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K. Loganathan and A. Anandan contributed equally to this work as the first authors

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Loganathan, K., Anandan, A., Purushothaman, M. et al. Synthesis, crystal structure, Hirshfeld surface analysis, and DFT studies of 2-bromo-4,6-bis(dibromoacetyl)resorcinol. Struct Chem 35, 627–640 (2024). https://doi.org/10.1007/s11224-023-02221-0

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