Synthesis, crystal structures and DFT calculations of two schiff base derivatives of (2-amino-5-ethyl-thiophen-3-yl)-(2-chloro-phenyl)-methanone

Kaur, M. and Jasinski, J. P. and Anderson, B. J. and Yathirajan, H. S. and Byrappa, K. (2015) Synthesis, crystal structures and DFT calculations of two schiff base derivatives of (2-amino-5-ethyl-thiophen-3-yl)-(2-chloro-phenyl)-methanone. JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 45 (4). pp. 193-201. ISSN 1572-8854

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Official URL: https://doi.org/10.1007/s10870-015-0580-4

Abstract

Two new Schiff base derivatives of (2-amino-5-ethyl-thiophen-3-yl)-(2-chloro-phenyl)-methanone, namely C22H19N2O5SCl (I) and C20H15N2O3SCl (II), have been synthesized and characterized by means of NMR, single-crystal X-ray diffraction and density functional theory geometry optimization and molecular orbital calculations. Compound (I) crystallizes in the triclinic space group P-1, with a = 7.8235(6) , b = 10.3256(5) , c = 13.6678(9) , alpha = 82.597(5)A degrees, beta A = 74.759(6)A degrees, gamma A = 89.968(5)A degrees, V = 1055.96(12) (3) and Z = 2. Compound (II) also crystallizes in the triclinic space group P-1, with a = 8.0644(7) , b = 10.7984(9) , c = 10.8191(9) , alpha = 104.142(7)A degrees, beta = 92.660(7)A degrees, gamma = 93.292(7)A degrees, V = 910.31(13) (3) and Z = 2. Geometry optimization calculations for each compound support these observations. Both compounds display R (2) (2) (10) ring motifs formed by weak C center dot center dot center dot H center dot center dot center dot O intermolecular interactions and contribute to crystal packing. Additionally, the frontier molecular orbitals of each complex 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 has been proposed. Synthesis, crystal structures, density functional theory (DFT) geometry optimization and molecular orbital surface calculations of two new Schiff base derivatives of (2-amino-5-ethyl-thiophen-3-yl)-(2-chloro-phenyl)-methanone: (2-chloro-phenyl)-{2-(4,5-dimethoxy-2-nitro-benzylidene)-amino]-5-et hyl-thiophen-3-yl}-methanone, (I): C22H19N2O5SCl and (2-chloro-phenyl)-{5-ethyl-2-(4-nitro-benzylidene)-amino]-thiophen-3 -yl}-methanone (II): C20H15N2O3SCl. GRAPHICS] .

Item Type: Article
Subjects: C Chemical Science > Chemistry
D Physical Science > Material Science
Divisions: Department of > Chemistry
Department of > Material Science
Depositing User: Shrirekha N
Date Deposited: 12 Jun 2019 09:33
Last Modified: 06 Jul 2019 05:42
URI: http://eprints.uni-mysore.ac.in/id/eprint/2756

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