Synthesis, crystal structures and DFT calculations of three schiff base derivatives of (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-phenylmethanone

Kaur, Manpreet and Anderson, B. J. and Yathirajan, H. S. and Byrappa, K. (2016) Synthesis, crystal structures and DFT calculations of three schiff base derivatives of (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-phenylmethanone. Journal of Chemical Crystallography, 146 (1). pp. 44-56. ISSN 1572-8854

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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.

Item Type:	Article
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Manjula P Library Assistant
Date Deposited:	13 Jun 2019 10:30
Last Modified:	13 Jun 2019 10:30
URI:	http://eprints.uni-mysore.ac.in/id/eprint/3011

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