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Synthesis, Crystal Structures and DFT Calculations of Three Schiff Base Derivatives of (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-phenylmethanone

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Abstract

Three new Schiff base derivatives of (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-phenylmethanone, namely, C23H21NO3S (I), C24H22N2O5S (II) and C26H28N2O2S (III) have been synthesized and characterized by NMR, single-crystal X-ray diffraction and DFT molecular orbital calculations. Compound (I) crystallizes in the orthorhombic space group P212121, with Z = 4 in cells with a = 5.02536(8) Å, b = 17.5927(3) Å, c = 21.2134(4) Å, V = 1875.47(5) Å3 and displays weak C–H···O intermolecular interactions which contribute to crystal packing. Compound (II) crystallizes in the monoclinic space group P21/c, with Z = 4 in cells with a = 11.2263(2) Å, b = 19.7401(3) Å, c = 10.0202(2) Å, β = 108.565(2)°, V = 2105.00(8) Å3 and displays weak C–H···O intermolecular interactions forming zig-zag chains along the b axis and weak π–π stacking interactions which influence crystal packing. Compound (III) also crystallizes in the monoclinic space group P21/c, with Z = 4 in cells with a = 10.9599(2) Å, b = 11.9287(3) Å, c = 17.0626(4) Å, β = 97.680(2)°, V = 2210.71(8) Å3 and displays weak C–H···O intermolecular interactions which contribute to crystal packing. Additionally, the DFT frontier molecular orbitals of each compound are displayed and correlation between the calculated molecular orbital energies (eV) for the surfaces of the frontier molecular orbitals to the electronic excitation transitions from the absorption spectra of each compound has been proposed.

Graphical Abstract

Synthesis, crystal structures, density functional theory (DFT) and molecular orbital surface calculations of three new Schiff base derivatives of (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-phenylmethanone: {2-[(2-hydroxy-3-methoxy-benzylidene)-amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}-phenylmethanone (I): C23H21NO3S; {2-[(4,5-dimethoxy-2-nitro-benzylidene)-amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}-phenylmethanone, (II): C24H22N2O5S and {2-[(4-diethylamino-2-hydroxybenzylidene)-amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}-phenylmethanone, (III): C26H28N2O2S.

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Acknowledgments

MK is grateful to CPEPA–UGC for the award of a JRF and thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (Grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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Authors and Affiliations

  1. Department of Studies in Chemistry, University of Mysore, Mysore, 570 006, India

    Manpreet Kaur & Hemmige S. Yathirajan

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

    Jerry P. Jasinski & Brian J. Anderson

  3. Materials Science Center, University of Mysore, Vijyana Bhavan Building, Manasagangothri, Mysore, 570 006, India

    K. Byrappa

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  1. Manpreet Kaur
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  2. Jerry P. Jasinski
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Correspondence to Jerry P. Jasinski.

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Kaur, M., Jasinski, J.P., Anderson, B.J. et al. Synthesis, Crystal Structures and DFT Calculations of Three Schiff Base Derivatives of (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-phenylmethanone. J Chem Crystallogr 46, 44–56 (2016). https://doi.org/10.1007/s10870-015-0626-7

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