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Crystal Structure and Quantum Chemical Studies of a Novel Push–Pull Enaminone: 3-Chloro-4-((4-bromophenyl)amino)pent-3-en-2-one

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Abstract

Reaction of 3-chloro-2,4-pentanedione with p-bromoaniline yields enaminone, 3-chloro-4-((4-bromophenyl)amino)pent-3-en-2-one. The structure of synthesized enaminone was identified by IR spectroscopy, proton NMR spectroscopy and single crystal X-ray crystallography. The enaminone was crystallized in monoclinic system with space group P21/c with cell coordinates a = 6.5123(4) Å, b = 12.1367(8) Å, c = 14.8002(9) Å, α = 90°, β = 93.512(2)°, γ = 90°, V = 1167.58(13) Å3, and Z = 4. Crystallographic analysis revealed that nitrogen and bromine atoms are in plane with aromatic ring. The aminopent-3-en-2-one chain forms a second plane and the angle between the two planes is observed to be 58.48°. Theoretical quantum chemical calculations have been performed on the studied enaminone using three different functionals—APFD, B3LYP & M06-2X. The geometric parameters of the optimized structure are in good agreement with experimental data obtained from X-ray structure.

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Acknowledgements

The authors are grateful to HEC, Government of Pakistan, for access to Scientific Instrumentation and Institute of Chemistry, University of the Punjab, Lahore for providing laboratory facilities.

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Authors and Affiliations

  1. Institute of Chemistry, University of the Punjab, Lahore, 54590, Pakistan

    Rahila Huma, Tariq Mahmud & Rubina Munir

  2. Department of Chemistry, Kinnaird College for Women, 93- Jail Road, Lahore, 54000, Pakistan

    Rahila Huma & Rubina Munir

  3. Department of Mathematics, Government College University, Faisalabad, Pakistan

    Nazeran Idrees

  4. Department of Applied Chemistry, Government College University, Faisalabad, Pakistan

    Muhammad Jawwad Saif

  5. Department of Physics, COMSATS University Islamabad, Lahore Campus, Lahore, 54000, Pakistan

    Nosheen Akbar

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  1. Rahila Huma
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  2. Tariq Mahmud
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Correspondence to Tariq Mahmud.

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Huma, R., Mahmud, T., Idrees, N. et al. Crystal Structure and Quantum Chemical Studies of a Novel Push–Pull Enaminone: 3-Chloro-4-((4-bromophenyl)amino)pent-3-en-2-one. J Chem Crystallogr 50, 187–197 (2020). https://doi.org/10.1007/s10870-019-00786-5

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