Synthesis, characterization, spectroscopic properties, theoretical calculation, and antimicrobial activity of new aryldisulfonamides

WOS: 000289965000004New aryldisulfonamides were synthesized and characterized by FTIR, (1)H NMR, (13)C NMR, HETCOR, COSY, LC-MS and elemental analysis techniques. The compounds gave intense emissions, where lambda(max) = 405, 379 and 402 nm, upon irradiation by Ultra-Violet light. The photoluminescence quantum yields and long excited-state lifetimes of the compounds were calculated and were found to have photoluminescence quantum yields 39 +/- 1.8%, 45 +/- 2.2% and 34 +/- 1.4% and long excited-state lifetimes of 3.65 +/- 0.16, 4.17 +/- 0.20 and 3.15 +/- 0.12 ns, respectively. The photoluminescence intensities and quantum yields of compounds varied with the position of substituent on the ring and the chain length between aromatic rings. These novel compounds may be of interest as organic emitting materials for electroluminescent devices. The visible absorption maxima were calculated using time-depended density-functional theory (ID-OFT) and Zerner's intermediate neglect of differential overlap/spectroscopic (ZINDO/S) method in the gas phase. Further, the compounds were evaluated for in vitro antimicrobial activity against various microorganisms by microdilution and disk diffusion methods. (C) 2011 Elsevier B.V. All rights reserved.TUBITAKTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [TBAG 104 T 390, MAG 104M 367]; Gazi University Scientific Research ProjectGazi University [05/2008-05]The authors wish to thank TUBITAK for the financial support (TBAG 104 T 390 and (MAG 104M 367) and Gazi University Scientific Research Project (05/2008-05). We would also like to thank the Departments of Chemistry at Gazi University and Gaziantep University

Synthesis, crystal structure, antibacterial activities, and electrochemical studies of new N,N '-polymethylene bis-sulfonamides

WOS: 000301606200001Four disulfonamide derivatives (C2H5 center dot SO2 center dot NH)(2)(CH2)(n) (n = 2, 3, 4, 5) were synthesized and characterized by FTIR, H-1 NMR, C-13 NMR, HETCOR, LCMS and elemental analysis.Ethanesulfonamide-N,N'-pentamethylene bis was also characterized by X-ray single crystal diffraction measurement. The electrochemical characteristics of the disulfonamide derivatives were performed by cyclic voltammetry and chronoamperometry. H-1 and C-13 NMR chemical shifts of the compounds were calculated by using DFT-/B3LYP methods with a 6-311++G (d,p) basis set. Antibacterial activity and the structural relationship of the compounds showed that activity decreases proportionately to the increasing length of the carbon chain between NH groups, log P values, hydration energy and molecular volumes. Anodic peak potentials and HOMO values do not correlate with the activity, but reduction potential and LUMO decrease weakly with increasing activity. (C) 2011 Elsevier B.V. All rights reserved.TUBITAKTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [104T390]; Gazi University BAPGazi University [05/2006-33]This research was supported by TUBITAK Research Fund under Project No.: 104T390, Gazi University BAP (No. 05/2006-33)

BAZI DİSÜLFONAMİT TÜREVLERİ VE Cu(II) KOMPLEKSLERİNİN SENTEZİ, ANTİMİKROBİYAL AKTİVİTELERİNİN İNCELENMESİ, KANTİTATİF-YAPI-AKTİVİTE İLİŞKİLERİNİN DEĞERLENDİRİLMESİ

Bu çalışmada, genel formülü X-ph-SO2-NH-(CH2)n-NH-SO2-ph-X ( n = 2, 3, 4, 5 ve X= o-, m-, p-CH3) olan sekiz simetrik aromatik disülfonamit bileşiği o-, m-, ptoluensülfonil klorür ile bir seri diamin tepkimeye sokularak sentezlenmiştir. Yapıları element analizi, LCMS, 1H-NMR, 13C-NMR, COSY, HETCOR ve IR teknikleri ile aydınlatılmıştır. N,N\'-dimetilenbis (m-toluensülfonamit) (mtsen) ve N,N\'-trimetilenbis(p-toluensülfonamit) (ptspr) bileşiklerinin yapısı ayrıca Xışınları kırınım yöntemi ile incelenmiştir. [Cu(phen)2]L (L= n=3, X=p-CH3; n=4, X=p-CH3; n=5, X=p-CH3; n=2, X=m- CH3; n=4, X=m-CH3; n=2, X=o-CH3) kompleksleri sentezlenmiş ve yapıları LCMS, FTIR, iletkenlik teknikleri ile incelenmiştir. [Cu(phen)2](mtsen) ve [Cu(phen)2](otsen) komplekslerinin yapısı X-ışınları kırınım yöntemi ile aydınlatılmıştır. Disülfonamit türevlerinin in vitro antimikrobiyal aktiviteleri Escherichia coli ATCC 11230, Salmonella enterititis ATCC 13076, Bacillus magaterium RSKK v 5117, Bacillus cereus ATCC 6633, Staphylococcus aureus ATCC 25953 bakterilerine karşı disk difüzyon ve mikrodilüsyon metotları ile incelenmiştir. Bileşikler, Gram-negatif ve Gram-pozitif bakterilere karşı geniş spektrumlu aktivite göstermiştir. Gram- negatif bakterilere karşı Gram- pozitifler bakterilerden daha fazla aktivite sergilemektedir. 74 μg/mL MİK değeri ile otsen bileşiği Escherichia coli bakterisine karşı en yüksek aktivite göstermiştir. Bütün bileşikler Bacillus magaterium bakterisine karşı düşük aktiviteye sahiptir. En düşük aktiviteyi ise ptspen bileşiği 440 μg/mL değeri ile göstermiştir. Bir seri simetrik disülfonamit bileşiğinin (26 tane) Bacillus cereus ATCC 6633, Staphylococcus aureus ATCC ve Escherichia coli ATCC 1123 bakterilerine karşı antimikrobiyal aktiviteleri ile fizikokimyasal özellikleri ve topolojik parametreleri arasında korelasyon kurmak amacı ile Hansch analizi uygulanarak QSAR çalışması yapılmıştır. QSAR çalışması ile topolojik parametrelerden ortalama konektivite indisinin, 3χA en yüksek korelasyonu gösterdiği belirlenmiştir. QSAR model denklemleri çapraz validasyon ve LOO tekniği ile belirlenmiştir

Conformational analysis and nonlinear optical properties of the N, N '-pentamethylenebis(salicylideneiminato)manganase(II) complex

WOS: 000304429900024Conformational analysis of the tricyclic Schiff base chelate complex N,N'- pentamethylenebis(salicylideneiminato)manganese(II) is performed by means of the molecular mechanic (MM+), semi-empirical PM3 and density functional (B3LYP/LanL2DZ) methods, respectively. Eight starting structures of the complex are minimized. The structures of the three lowest minimum energy conformations of cyclooctane, boat-chair (bc), chair-chair (cc) and boat-boat (bb), are used as initial approximations to the geometry of the eight-membered chelate ring. The absolute-MEC (Mn-bc4) and the most unstable one (Mn-bb) originate from the boat-chair-shaped form of the eight-membred cycle, differing in the position of the metal atom. After the conformational analysis of the tricyclic Schiff base chelate complex, nonlinear optical properties and optical band gap (EHOMO-LUMO) were calculated with B3LYP/LanL2DZ level of theory for all conformations. The frontier molecular orbital calculations clearly show the inverse relationship of optical band gap (EHOMO-LUMO) with the total static hyperpolarizability

Synthesis, characterization and anti-microbial evaluation of Cu(II), Ni(II), Pt(II) and Pd(II) sulfonylhydrazone complexes; 2D-QSAR analysis of Ni(II) complexes of sulfonylhydrazone derivatives

WOS: 000318209100016PubMed ID: 23466322Copper(II), nickel(II), platinum(II) and palladium(II) complexes with 2-hydroxy-1-naphthaldehyde-N-methylpropanesulfonylhydrazone (nafpsmh) derived from propanesulfonic acid-1 -methylhydrazide (psmh) were synthesized, their structure were identified, and antimicrobial activity of the compounds was screened against three Gram-positive and three Gram-negative bacteria. The results of antimicrobial studies indicate that Pt(II) and Pd(II) complexes showed the most activity against all bacteria. The crystal structure of 2-hydroxy-1-naphthaldehyde-N-methylpropanesulfonylhydrazone (nafpsmh) was also investigated by X-ray analysis. A series of Ni(II) sulfonyl hydrazone complexes (1-33) was synthesized and tested in vitro against Escherichia coli and Staphylococcus aureus. Their antimicrobial activities were used in the QSAR analysis. Four-parameter QSAR models revealed that nucleophilic reaction index for Ni and O atoms, and HOMO-LUMO energy gap play key roles in the antimicrobial activity. (c) 2013 Elsevier B.V. All rights reserved.Gazi University BAPGazi University [05/2010-43]The authors would like to thank Gazi University BAP (Grant No: 05/2010-43) for the financial support of this project

Conformational analysis, vibrational and NMR spectroscopic study of the methanesulfonamide-N,N '-1,2-ethanediylbis

WOS: 000303073300007PubMed ID: 22349891A conformational analysis of the methanesulfonamide-N,N'-1,2-ethanediylbis (msen) was performed by using vibrational and NMR spectroscopies as well as theoretical computations. The possible stable conformers of msen on its potential energy surface were investigated by semi-empirical PM5 method and appropriate structures were defined with B3LYP hybrid density functional theory (DFT) method along with the basis sets of different size and type. Six different rotational isomers were found as the result of DFT calculation. The two isomer, called trans-trans-gauche(+)-eclipsed, synperiplanar (ttg(+)-e,bis) and trans-gauche(+)-gauche(-)-staggered, antiplanar (tg(+)g(-)-s,anti), were considered in the vibrational spectral analysis. The infrared (4000-30 cm(-1)) and Raman (4000-60 cm(-1)) spectra of msen were measured in solid state. For a complete assignment of the vibrational spectra, DFT calculations at B3LYP/6311-G(d,p) theory level combined with scaled quantum mechanics force field (SQMFF) methodology was performed. Furthermore, C-13 and H-1 NMR analyses were performed for six conformers at B3LYP/6-311++G(d,p) level of theory and compared with the experimental findings. Results from experimental and theoretical data showed the ttg(+)-e,bis to be the most stable form of a msen molecule. (C) 2012 Elsevier B.V. All rights reserved

Experimental and theoretical studies on methanesulfonic acid 1-methylhydrazide: Antimicrobial activities of its sulfonyl hydrazone derivatives

WOS: 000272896300009Methanesulfonic acid 1-methylhydrazide (msmh) and its sulfonyl hydrazone derivatives, salicylaldehyde-N-methylmethanesulfonylhydrazone (salmsmh) and 2-hydroxy-1-naphthaldehyde-N-methylmethanesulfonylhydrazone (nafmsmh) were synthesized and characterized by using FT-IR, H-1 NMR, C-13 NMR, LC-MS and elemental analysis Conformation analysis of msmh based on DFT/B3LYP/6-311G(d) method was performed. H-1 and C-13 shielding tensors of msmh for the most stable conformer were calculated with GIAO/DFT/B3LYP/6-311++G(2d, 2p) methods in vacuo, and various solvents such as DMSO, THF, acetonitrile, methanol and aqueous solution. The harmonic vibrational wavenumbers for the most stable conformer were calculated using at B3LYP/6-311G(d) level Antimicrobial activity of the compounds was also screened against Gram-positive bacteria (Staphylococcus aureus ATCC 25923. Bacillus cereus RSKK 863)and Gram-negative bacteria(Escherichia coli ATCC 11230, Salmonella enterititis ATCC 40376, Pseudomonos aeruginosa ATCC 28753) by both disc diffusion and micro dilution methods. (C) 2009 Elsevier B.V. All rights reservedTUBITAKTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [104 T 390]; Gazi University BAPGazi University [05/2005-59]The authors thank the TUBITAK (Grant No 104 T 390) and Gazi University BAP (Grant No. 05/2005-59) for the financial support of this project

Biologically active Schiff bases containing thiophene/furan ring and their copper(II) complexes: Synthesis, spectral, nonlinear optical and density functional studies

WOS: 000378453100030Schiff bases; 1,8-bis(thiophene-2-carboxaldimine)-p-menthane (L-1) and 1,8-bis(furan-2-carboxaldimine)-p-menthane (L-2) have been synthesized and characterized by elemental analysis, H-1-C-13 NMR, UV-vis, FT-IR and LC-MS methods. H-1 and C-13 shielding tensors for L-1 and L-2 were calculated with GIAO/DFT/B3LYP/6-311++G(d,p) methods in CDCl3. The vibrational band assignments, nonlinear optical (NLO) activities, frontier molecular orbitals (FMOs) and absorption spectrum have been investigated by the same basis set. Schiff base-copper(II) complexes have been synthesized and structurally characterized with spectroscopic methods, magnetic and conductivity measurements. The spectroscopic data suggest that Schiff base ligands coordinate through azomethine-N and thiophene-S/furan-O donors (as SNNS and ONNO chelating systems) to give a tetragonal geometry around the copper(II) ions. Schiff bases and Cu(II) complexes have been screened for their biological activities on different species of pathogenic bacteria, those are, Gram positive bacteria: Bacillus subtitilus, Yersinia enterotica, Bacillus cereus, Listeria monocytogenes, Micrococcus luteus and Gram negative bacteria: Escherichia coli, Pseudomonas aeroginosa, Shigella dysenteriae, Salmonella typhi, Kiebsiella pseudomonas by using microdilution technique (MIC values in mM). Biological activity results show that Cu(II) complexes have higher activities than parent ligands and metal chelation may affect significantly the antibacterial behavior of the organic ligands. (C) 2016 Elsevier B.V. All rights reserved.Gazi UniversityGazi University [05/2007-09]The authors thank the Gazi University, vide Project no (05/2007-09) for financial support

Synthesis, characterization and antimicrobial activity of new butanesulfonamides

WOS: 000248688400281

Synthesis, characterization and antimicrobial activity of m-toluenesulfonamide, N,N '-1,2-ethanediylbis (mtsen) and [Cu(II)(phenanthroline)(2)]mtsen complex

WOS: 000311174800018M-toluenesulfonamide, N,N'-1,2-ethanediylbis (a disulfonamide compound, mtsen) and [Cu(II)(phenanthroline)(2)]mtsen compounds were newly synthesized. The molecular structure of mtsen was investigated by using elemental analyses, liquid chromatography-mass spectrometry (LC-MS), X-ray diffraction, Fourier transform infrared spectroscopy (FT-IR), dispersive Raman spectroscopy, H-1, C-13, heteronuclear chemical-shift correlation (HETCOR) and correlation spectroscopy (COSY) NMR spectroscopies. The FT-IR, dispersive Raman and far-infrared spectra of mtsen were recorded at room-temperature and discussed assisted with B3LYP/6-311G(d,p) level of theory along with scaled quantum mechanics force field (SQM-FF) method. Furthermore, H-1 and C-13 NMR analyses were performed at B3LYP/6-311++G(d,p) theory level using gauge including atomic orbital (CIAO) method and compared with the experimental findings. Further analyses were also made for [Cu(II)(phenanthroline)(2)]mtsen complex by using elemental analysis, LC-MS, magnetic susceptibility; conductivity measurement and FT-IR. The antibacterial activities of synthesized compounds were studied against some Gram-positive and Gram-negative bacteria by using the microdilution and disk diffusion method. The biological activity screening showed that complex have more activity than ligand against the tested bacteria. (C) 2012 Elsevier B.V. All rights reserved