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Synthesis, Crystal Structures and DFT Calculations of Two New Phenol-Based Ester Derivatives

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Abstract

Two new phenol-based ester derivatives, namely C13H9ClO2 (I) and C20H14O4 (II) have been synthesized and characterized by NMR spectroscopy, single crystal X-ray diffraction and density functional theory (DFT) geometry optimization and molecular orbital calculations. Compound I crystallizes in the orthorhombic space group Pca2(1),with a = 7.6297 (5) Å, b = 5.5875 (3) Å, c = 26.1624 (12) Å, α = β = γ = 90°, V = 1115.33(11) Å3 and Z = 4. Compound II crystallizes in the triclinic space group P \(\bar 1\), with a = 5.7970 (4) Å, b = 8.1366 (8) Å, c = 8.8057 (9) Å, α = 83.246 (8)°, β = 72.138 (8)°, γ = 76.696 (8)°, V = 384.22 (6) Å3 and Z = 1. Geometry optimization calculations for each compound is consistent with these observations. A comparison of the dihedral angles between mean planes of the benzene rings in the crystal with the DFT theoretical calculations and weak intermolecular hydrogen bond interactions has been included for each molecule. Electronic transitions have been predicted by DFT Molecular Orbital calculations and compared with experimental absorption spectra.

Graphical Abstract

Synthesis, crystal structures, DFT geometry optimization and molecular orbital surface calculations of two new phenol-based ester derivatives of 4-chlorophenyl benzoate, (I): C13H9ClO2 and 1,4-phenylene dibenzoate, (II): C20H14O4.

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Acknowledgments

SKG thanks UGC (University Grants Commission, New Delhi) for financial assistance [Grant No. F.37-500/2009 (SR)]. JPJ acknowledges the NSF–MRI (Grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

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Authors and Affiliations

  1. School of Studies in Chemistry, Jiwaji University, Gwalior, 474 011, India

    Javeed A. Ganaie, Jubin Kumar & Sushil K. Gupta

  2. Department of Chemistry, Howard University, 525 College Street NW, Washington, DC, 20059, USA

    Ray J. Butcher

  3. Department of Chemistry, Keene State College, 229 Main Street, Keene, NH, 03435-2001, USA

    Jerry P. Jasinski

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  1. Javeed A. Ganaie
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  2. Jubin Kumar
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Correspondence to Sushil K. Gupta.

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Ganaie, J.A., Kumar, J., Butcher, R.J. et al. Synthesis, Crystal Structures and DFT Calculations of Two New Phenol-Based Ester Derivatives. J Chem Crystallogr 46, 93–104 (2016). https://doi.org/10.1007/s10870-016-0632-4

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  • DOI: https://doi.org/10.1007/s10870-016-0632-4

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