Synthesis, spectral characterization, thermal behaviour, antibacterial activity and DFT calculation on N′-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide and N′-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 145; pp. 98 - 109
• Main Authors: Bharty, M.K., Dani, R.K., Kushawaha, S.K., Prakash, Om, Singh, Ranjan K., Sharma, V.K., Kharwar, R.N., Singh, N.K.
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 15.06.2015
• Subjects: Anti-Bacterial Agents - pharmacology; Antibacterial property; Bacteria - drug effects; Benzamides - chemical synthesis; Benzamides - chemistry; Benzamides - pharmacology; Carbon-13 Magnetic Resonance Spectroscopy; Crystal structure; Crystallography, X-Ray; DFT calculation; Differential Thermal Analysis; Humans; Hydrazines - chemical synthesis; Hydrazines - chemistry; Hydrazines - pharmacology; Hydrogen Bonding; Inhibitory Concentration 50; Models, Molecular; Molecular Conformation; NLO property; Nonlinear Dynamics; Optical Phenomena; Proton Magnetic Resonance Spectroscopy; Quantum Theory; Spectroscopy, Fourier Transform Infrared; Static Electricity; Temperature; Thermal stability; DFT calculation; Antibacterial property; Hydrogen bonding; Thermal stability; Crystal structure; NLO property
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2015.02.055

Two new compounds N′-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide {Hbmshb (1)} and N′-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester {H2mbhce (2)} have been synthesized. Inter and intra molecular hydrogen bonding link two molecules and provide linear chain structure. In addition to this, compound 2 is stabilized by CH⋯π and NH⋯π interactions. Molecular geometry from X-ray analysis, geometry optimization, charge distribution, bond analysis, frontier molecular orbital (FMO) analysis and non-linear optical (NLO) effects have been performed using the density functional theory (DFT) with the B3LYP functional. The bioefficacy of compounds has been examined against the growth of bacteria to evaluate their anti-microbial potential. [Display omitted] •Two new N-aroyl-hydrazinecarbodithioic acid esters have been reported.•Both compounds show NLO behaviour better than the urea.•Structural data from X-ray are corroborated well with DFT calculations.•Compound 2 shows antibacterial activity but lower than the standard drugs.•These compounds may be potentially used against weak bacterial pathogens. Two new compounds N′-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide {Hbmshb (1)} and N′-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester {H2mbhce (2)} have been synthesized and characterized with the aid of elemental analyses, IR, NMR and single crystal X-ray diffraction data. Compounds 1 and 2 crystallize in orthorhombic and monoclinic systems with space group Pna21 and P21/n, respectively. Inter and intra molecular hydrogen bonding link two molecules and provide linear chain structure. In addition to this, compound 2 is stabilized by CH⋯π and NH⋯π interactions. Molecular geometry from X-ray analysis, geometry optimization, charge distribution, bond analysis, frontier molecular orbital (FMO) analysis and non-linear optical (NLO) effects have been performed using the density functional theory (DFT) with the B3LYP functional. The bioefficacy of compounds has been examined against the growth of bacteria to evaluate their anti-microbial potential. Compounds 1 and 2 are thermally stable and show NLO behaviour better than the urea crystal.