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New Tridentate Schiff Base, Product of Condensation of 4-Methyl-7-hydroxy-8-formylcoumarin and N-Aminomercaptotriazole: Synthesis, Structure, and Complex Formation

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Abstract

A new Schiff base was prepared by the reaction of 4-methyl-7-hydroxy-8-formylcoumarin with N-aminomercaptotriazole. In solution and in solid phase the compound was shown to exist in the thione form. The compound reacts with Cu(II), Ni(II), Zn(II) and Cd(II) ions depending on the metal salt to give complexes of composition ML2 or MHLX, where HL is monodeprotonated form of the ligand. Cu(II) and Ni(II) complexes were studied by spectral and magnetochemical methods. The Zn(II) and Cd(II) complexes exhibit fluorescence.

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References

  1. Krause, M., Rouleau, A., Stark, H., Luger, P., Lipp, R., Garbarg, M., Schwartz, J.-C., and Schunack, W., J. Med. Chem., 1995, vol. 38, no. 20, p. 4070. doi 10.1021/jm00020a022

    Article  CAS  PubMed  Google Scholar 

  2. Hui, M.B.V., Lien, E.J., and Trousdale, M.D., Antivir. Res., 1994, vol. 24, no. 4, p. 261. doi 10.1016/0166-3542(94)90074-4

    Article  CAS  PubMed  Google Scholar 

  3. Lewinski, J., Zachara, J., Justyniak, I., and Dranka, M., Coord. Chem. Rev., 2005, vol. 249, nos. 11–12, p. 1185. doi 10.1016/j.ccr.2004. 11.013

    Article  CAS  Google Scholar 

  4. Kleij, A.W., Chem. Eur. J., 2008, vol. 14, no. 34, p. 10520. doi 10.1002/chem.200801149

    Article  CAS  PubMed  Google Scholar 

  5. Garnovskii, A.D., Nivorozhkin, A.L., and Minkin, V.I., Coord. Chem. Rev., 1993, vol. 126, nos. 1–2, p. 1. doi 10.1016/0010-8545(93)85032-Y.

    Article  CAS  Google Scholar 

  6. Garnovskii, A.D., Burlov, A.S., Vasil’chenko, I.S., Garnovskii, D.A., Uraev, A.I., and Sennikova, E.V., Russ. J. Coord. Chem., 2010, vol. 36, no. 2, p. 81. doi 10.1134/S1070328410020016

    Article  CAS  Google Scholar 

  7. Chattopadhyay, A., Meier, M., Ivaninskii, S., Burkhard, P., Speroni, F., Campanini, B., Bettati, S., Mozzarelli, A., Rabeh, W.M., Li, L., and Cook, P.F., Biochemistry, 2007, vol. 46, no. 28, p. 8315. doi 10.1021/bi602603c

    Article  CAS  PubMed  Google Scholar 

  8. Montagner, C., de Souza, S.M., Groposo, C., Delle Monache, F., Smania, E.F.A., and Smania, Jr.A., Z. Naturforsch. C, 2008, vol. 63, nos. 1–2, p. 21. doi 10.1515/znc-2008-1-205

    Article  CAS  PubMed  Google Scholar 

  9. Minkin, V.I., Tsukanov, A.V., Dubonosov, A.D., and Bren, V.A., J. Mol. Struc., 2011, vol. 998, nos. 1–3, p. 179. doi 10.1016/j.molstruc.2011.05.029

    Article  CAS  Google Scholar 

  10. Uzhinov, B.M. and Khimich, M.N., Russ. Chem. Rev., 2011, vol. 80, no. 6, p. 553. doi 10.1070/RC2011v080n06ABEH004144

    Article  CAS  Google Scholar 

  11. Ohshima, A., Momotake, A., Arai, T., J. Photochem. Photobiol. (A), 2004, vol. 162, nos. 2–3, p. 473. doi 10.1016/S1010-6030(03)00388-5

    Article  CAS  Google Scholar 

  12. Harada, J., Uekusa, H., and Ohashi, Y., J. Am. Chem. Soc., 1999, vol. 121, no. 24, p. 5809. doi 10.1021/ja9842969

    Article  CAS  Google Scholar 

  13. Seo, K.D., Song, H.M., Lee, M.J., Pastore, M., Anselmi, C., De Angelis, F., Nazeeruddin, M.K., Graetzel, M., and Kim, H.K., Dyes Pigments, 2011, vol. 90, no. 3, p. 304. doi 10.1016/j.dyepig.2011.01.009

    Article  CAS  Google Scholar 

  14. Traven’, V.F., Ivanov, I.V., Panov, A.V., Safronova, O.B., and Chibisova, T.A., Russ. Chem. Bull., 2008, vol. 57, no. 9, p. 1989. doi 10.1007/s11172-008-0267-5

    Article  CAS  Google Scholar 

  15. Bagihalli, G.B., Avaji, P.G., Badami, P.S., and Patil, S.A., J. Coord. Chem., 2008, vol. 61, no. 17, p. 2793. doi 10.1080/00958970801975109

    Article  CAS  Google Scholar 

  16. Yan, M.-H., Li, T.-R., and Yang, Z.-Y., Inorg. Chem. Commun., 2011, vol. 14, no. 3, p. 463. doi 10.10316/j.inoche.2010.12.027

    Article  CAS  Google Scholar 

  17. An, J.-M., Yang, Z.-Y., Yan, M.-H., and Li, T.-R., J. Luminescence, 2013, vol. 139, p. 79. doi 10.10316/j.jlumin.2013.02.019

    Article  CAS  Google Scholar 

  18. Xie, L., Chen, Y., Wu, W., Guo, H., Zhao, J., and Yu, X., Dyes Pigments, 2012, vol. 92, no. 3, p. 1361. doi 10.1016/j. dyepig.2011.09.023

    Article  CAS  Google Scholar 

  19. Kulkarni, A.D., Bagihalli, G.B., Patil, S.A., and Badami, P.S., J. Coord. Chem., 2009, vol. 21, no. 18, p. 3060. doi 10.1080/00958970902914569

    Article  CAS  Google Scholar 

  20. Chen, F., Liu, G., Shi, Y., Xi, P., Cheng, J., Hong, J., Shen, R., Yao, X., Bai, D., and Zeng, Z., Talanta, 2014, vol. 124, p. 139. doi 10.1016/j.talanta.2014.02.034

    Article  CAS  PubMed  Google Scholar 

  21. Singh, K., Puri, P., Kumar, Y., and Sharma, C., Phosphorus, Sulfur, Silicon, Relat. Elem., 2013, vol. 188, no. 10, p. 1462. doi 10.1080/10426507.2012.757609

    Article  CAS  Google Scholar 

  22. Kumar, M.S., Tamilarasan, R., and Sreekanth, A., Spectrochim. Acta. (A), 2011, vol. 79, no. 2, p. 370. doi 10.1016/j.saa.2011.03.030

    Article  CAS  Google Scholar 

  23. Heshmatpour, F., Ghassemzadeh, M., Semsarha, M., and Neumuller, B., Z. Anorg. Allg. Chem., 2007, vol. 633, no. 3, p. 465. doi 10.1002/zaac.200600342

    Article  CAS  Google Scholar 

  24. Ko, K.C., Wu, J.-S., Kim, H.J., Kwon, P.S., Kim, J.W., Bartsch, R.A., Lee, J.Y., and Kim, J.S., Chem. Commun., 2011, vol. 47, no. 11, p. 3165. doi 10.1039/C0CC05421F

    Article  CAS  Google Scholar 

  25. Talrose, V., Yermakov, A.N., Usov, A.A., Goncharova, A.A., Leskin, A.N., Messineva, N.A., Trusova, N.V., and Efimkina, M.V., UV-Visible Spectra in NIST Chemistry. NIST Standard Reference Database Number 69, Linstrom, P.J. and Mallard, W.G., Eds., Gaithersburg: National Institute of Standards and Technology, 2017. doi 10.18434/T4D303

  26. Montanaro, D., Lavecchia, R., Petrucci, E., and Zuorro, A., Chem. Eng. J., 2017, vol. 323, p. 512. doi 10.1016/j.cej.2017.04.129

    Article  CAS  Google Scholar 

  27. Orysyk, S.I., Repich, G.G., Bon, V.V., Dyakonenko, V.V., Orysyk, V.V., Zborovskii, Yu.L., Shishkin, O.V., Pekhnyo, V.I., and Vovk, M.V., Inorg. Chim. Acta, 2014, vol. 423, p. 496. doi 10.1016/j.ica.2014.08.056

    Article  CAS  Google Scholar 

  28. Parker, C.A., Photoluminescence of Solutions, Amsterdam: Elsevier, 1968.

    Google Scholar 

  29. Chernyshov, A.A., Veligzhanin, A.A., and Zubavichus, Y.V., Nucl. Instrum. Methods Phys. Res. (A), 2009, vol. 603, nos. 1–2, p. 95. doi 10.1016/j.nima.2008.12.167

    Article  CAS  Google Scholar 

  30. Newville, M., J. Synchrotron Rad., 2001, vol. 8, no. 2, p. 96. doi 10.1107/S0909049500016290

    Article  CAS  Google Scholar 

  31. Zabinski, S.I., Rehr, J.J., Ankudinov, A., Albers, R.C., and Eller, M.J., Phys. Rev. (B), 1995, vol. 52, no. 4, p. 2995. doi 10.1103/PhysRevB.52.2995

    Article  Google Scholar 

  32. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven, Jr.T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision, E.1., 2003.

    Google Scholar 

  33. Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, p. 11623. doi 10.1021/j100096a001

    Article  CAS  Google Scholar 

  34. Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648. doi 10.1063/1.464913

    Article  CAS  Google Scholar 

  35. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785. doi 10.1103/PhysRevB.37.785

    Article  CAS  Google Scholar 

  36. Tsipis, A.C., Coord. Chem. Rev., 2014, vol. 272, p. 1. doi 10.1016/j.ccr.2014.02.023

    Article  CAS  Google Scholar 

  37. Wang, Y.-G., J. Phys. Chem. (A), 2009, vol. 113, no. 41, p. 10867. doi 10.1021/jp904007j

    Article  CAS  Google Scholar 

  38. Furche, F. and Rappoport, D., Theor. Comput. Chem., 2005, vol. 16, p. 93. doi 10.1016/S1380-7323(05)80020-2

    Article  CAS  Google Scholar 

  39. Miertus, S., Scrocco, E., and Tomasi, J., Chem. Phys., 1981, vol. 55, p. 117. doi 10.1016/0301-0104(81)85090-2

    Article  CAS  Google Scholar 

  40. Cammi, R. and Tomasi, J., J. Comput. Chem., 1995, vol. 16, p. 1449. doi 10.1002/jcc.540161202

    Article  CAS  Google Scholar 

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Correspondence to L. D. Popov.

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Original Russian Text © L.D. Popov, S.А. Borodkin, I.S. Vasil’chenko, V.G. Vlasenko, G.S. Borodkin, Ya.V. Zubavichus, S.I. Levchenkov, Yu.P. Tupolova, Yu.V. Revinskii, I.N. Shcherbakov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 7, pp. 1149–1158.

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Popov, L.D., Borodkin, S.A., Vasil’chenko, I.S. et al. New Tridentate Schiff Base, Product of Condensation of 4-Methyl-7-hydroxy-8-formylcoumarin and N-Aminomercaptotriazole: Synthesis, Structure, and Complex Formation. Russ J Gen Chem 88, 1441–1450 (2018). https://doi.org/10.1134/S1070363218070150

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