The title molecule, (E)-3-chloro-N-((5-nitrothiophen-2-yl)methylene)aniline, (C(11)H(7)ClN(2)O(2)S), was synthesized and characterized by IR and single-crystal X-ray structure determination. The compound crystallizes in the monoclinic space group P2(1)/c. In addition, the molecular geometry, vibrational frequencies and frontier molecular orbitals analysis of the title compound in the ground state have been calculated by using the PM3 semi-empirical, HF/6-31G(d) and B3LYP/6-31G(d) ab initio methods. The results of the optimized molecular structure are exhibited and compared with the experimental X-ray diffraction and the calculated results are show that the optimized geometry can well reproduce the crystal structure. The Schiff base compounds are very important in medicinal and pharmaceutical fields because of their wide spectrum of biological activities. Most of them show biological activities such as antimicrobial, antifungal as well as antitumor activity. Therefore, (C(11)H(7)ClN(2)O(2)S) was investigated for their antimicrobial activities, Gram-positive and Gram-negative bacteria.
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