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Antibacterial Investigation and Structural Study on Few ortho-Mercapto-azo Compounds by Spectroscopic Techniques and DFT Calculation
Corresponding Author(s) : Murshida Karim
Asian Journal of Chemistry,
Vol. 34 No. 8 (2022): Vol 34 Issue 8, 2022
Abstract
An efficient method has been applied for the synthesis of bivalent ortho-mercapto-azo compounds by using green reduction, condensation using ionic liquid and green debenzylation. These greener steps provide the benefits like higher yields, shorter reaction times and simple work-up. Density functional theory (DFT) calculation and XRD analysis proved the ionic nature of these compounds as 2-arylbenzo-1-thia-2,3-diazol-2-ium (BTD+) bromide due to intramolecular cyclization between electrophilic sulfur atom and ortho-azo group. Some extent of LUMO orbital is present in electrophilic sulfur atom in BTD+ bromides. These sulfenyl bromides were also found to be active against antibacterial strains.
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References
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A.J. Parker and N. Kharasch, Chem. Rev., 59, 583 (1959); https://doi.org/10.1021/cr50028a003
S. Oae, Organic Sulfur Chemistry: Structure and Mechanism, CRC Press (1991).
J.L. Kice and N.A. Favstritsky, J. Am. Chem. Soc., 91, 1751 (1969); https://doi.org/10.1021/ja01035a025
S.H. Smallcombe and M.C. Caserio, J. Am. Chem. Soc., 93, 5826 (1971); https://doi.org/10.1021/ja00751a041
L. Craine and M. Raban, Chem. Rev., 89, 689 (1989); https://doi.org/10.1021/cr00094a001
N. Kharasch, S.J. Potempa and H.L. Wehrmeister, Chem. Rev., 39, 269 (1946); https://doi.org/10.1021/cr60123a004
Q.T. Do, D. Elothmani and G. Le Guillanton, Tetrahedron Lett., 39, 4657 (1998); https://doi.org/10.1016/S0040-4039(98)00871-5
M. Iwasaki, T. Fujii, K. Nakajima and Y. Nishihara, Angew. Chem. Int. Ed., 53, 13880 (2014); https://doi.org/10.1002/anie.201408121
G.H. Schmid, A. Modro, F. Lenz, D.G. Garratt and K. Yates, J. Org. Chem., 41, 2331 (1976); https://doi.org/10.1021/jo00875a025
W.H. Mueller and P.E. Butler, J. Am. Chem. Soc., 90, 2075 (1968); https://doi.org/10.1021/ja01010a029
N. Kharasch, J. Chem. Educ., 33, 585 (1956); https://doi.org/10.1021/ed033p585
I.V.E. Koval, Russ. Chem. Rev., 64, 731 (1995); https://doi.org/10.1070/RC1995v064n08ABEH000172
J. Tan, F.S. Liang, Y.M. Wang, X. Cheng, Q. Liu and J. Yuan, Org. Lett., 10, 2485 (2008); https://doi.org/10.1021/ol800765s
A. Burawoy and C.E. Vellins, J. Chem. Soc., 90 (1954); https://doi.org/10.1039/jr9540000090
K. Sanjib, P. Kabita, P. Barman, D. Hazarika and S.K. Bhattacharjee, Acta Crystallogr. Sect. E Struct. Rep. Online, 60, 179 (2004); https://doi.org/10.1107/S1600536803029702
N. Ahmed, T. Bhattacharjee, P. Barman and S.K. Bhattacharjee, Synth. Commun., 43, 2663 (2013); https://doi.org/10.1080/00397911.2012.733476
A. Burawoy and A. Chaudhuri, J. Chem. Soc., 653 (1956); https://doi.org/10.1039/jr9560000653
P. Barman, S.K. Bhattacharjee and T. Bhattacharjee, Synth. Commun., 41, 2870 (2011); https://doi.org/10.1080/00397911.2010.515361
T. Bhattacharjee, M. Kalita, D. Chakravarty, P. Barman and V.G. Puranik, J. Coord. Chem., 67, 1702 (2014); https://doi.org/10.1080/00958972.2014.922683
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A. Fontana and E. Scoffone, Methods Enzymol., 25, 482 (1972); https://doi.org/10.1016/S0076-6879(72)25044-3
B. Hellman, J. Lernmark, J. Sehlin, M. Söderberg and I.-B. Täljedal, Endocrinology, 99, 1398 (1976); https://doi.org/10.1210/endo-99-5-1398
G.K. Helmkamp, D.C. Owsley, W.M. Barnes and H.N. Cassey, J. Am. Chem. Soc., 90, 1635 (1968); https://doi.org/10.1021/ja01008a039
O. Bortolini, A. Guerrini, V. Lucchini, G. Modena and L. Pasquato, Tetrahedron Lett., 40, 6073 (1999); https://doi.org/10.1016/S0040-4039(99)01261-7
M.K. Chaudhuri, A.T. Khan, B.K. Patel, D. Dey, W. Kharmawophlang, T.R. Lakshmiprabha and G.C. Mandal, Tetrahedron Lett., 39, 8163 (1998); https://doi.org/10.1016/S0040-4039(98)01818-8
M. Benz, A.M. van der Kraan and R. Prins, Appl. Catal. A., 172, 149 (1998); https://doi.org/10.1016/S0926-860X(98)00111-2
P.J. Das and J. Das, RSC Adv., 5, 11745 (2015); https://doi.org/10.1039/C4RA12298D
A.D. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
C. Lee, W. Yang and R.G. Parr, Phys. Rev., 37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785