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Synthesis, structure, and properties of new phosphorus Schiff bases

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Abstract

A series of new Schiff bases has been synthesized on the basis of (2-aminophenyl)triphenyl-phosphonium chloride and substituted salicylaldehydes. The structure of the prepared compounds has been established by means of IR, UV, and 1H NMR spectroscopy, as well as DFT B3LYP/6-31G(d,p) quantum-chemical simulation. The possible tautomerism and certain properties of the azomethines, including complex formation, have been studied.

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References

  1. Shoichiro, Y., Coord. Chem. Rev., 1999, vol. 190–192, p. 537.

    Google Scholar 

  2. Garnovskii, A.D., and Vasil’chenko, I.G., Usp. Khim., 2005, vol. 74, no. 3, p. 211.

    Google Scholar 

  3. Garnovskii, A.D., Koord. Khim., 1993, vol. 19, no. 5, p. 394.

    CAS  Google Scholar 

  4. Kogan, V. A., Kharabaev, N.N., Osipov, O.A., and Kochin, S.G., Zh. Strukt. Khim., 1981, vol. 22, no. 1, p. 126.

    CAS  Google Scholar 

  5. Minbaev, B.U., Shiffovy osnovaniya (Schiff Bases), Alma-Ata: Nauka, 1989.

    Google Scholar 

  6. Kuznetsov, V.V., and Prostakov, I.S., Khim. Geterotsikl. Soedin., 1990, no. 1, p. 5.

  7. Vigato, P.A., and Tamburini, S., Coord. Chem. Rev., 2004, vol. 248, p. 1717.

    Article  CAS  Google Scholar 

  8. Parr, J., and Slawin, A.M.Z., Inorg. Chim. Acta, 2000, vol. 303, no. 1, p. 116.

    Article  CAS  Google Scholar 

  9. Shi, P.-Y., and Liu, Y.-H., Organometallics, 2002, vol. 21, no. 15, p. 3203.

    Article  CAS  Google Scholar 

  10. Korupoju, S.R., Lai, R.-Y., Liu, Y.-H., Peng, S.-M., and Liu, S.-T., Inorg. Chim. Acta, 2005, vol. 358, no. 11, p. 3003.

    Article  CAS  Google Scholar 

  11. Doherty, S., Knight, J.G., Scanlan, T.H., Elsegood, R.Y., and Clegg, W., J. Organomet. Chem., 2002, vol. 650, nos. 1–2, p. 231.

    Article  CAS  Google Scholar 

  12. Dalili, S., Caiazzo, A., and Yudin, A.K., J. Organomet. Chem., 2004, vol. 689, no. 22, p. 3604.

    Article  CAS  Google Scholar 

  13. Faller, J.W., Mason, G., and Parr, J., J. Organomet. Chem., 2002, vol. 650, nos. 1–2, p. 181.

    Google Scholar 

  14. Cameron, P.A., Gibson, V.C., Redshaw, C., Segal, J.A., White, J.P., and Williams, D.J., J. Chem. Soc., Dalton Trans., 2002, vol. 2, no. 3, p. 415.

    Article  Google Scholar 

  15. Bhattacharyya, P., Loza, M.L., Parr, J., and Slawin, A.M.Z., J. Chem. Soc., Dalton Trans., 1999, no. 17, p. 2917.

  16. Dilworth, J.R., Howe, S.D., Hutson, A.J., Miller, J.R., Silver, J., Thompson, R.M., Harman, M., and Hursthouse, M.B., J. Chem. Soc., Dalton Trans., 1994, no. 24, p. 53.

  17. Bhattacharyya, P., Parr, J., and Slawin, A.M.Z., J. Chem. Soc. Dalton Trans., 1998, no. 21, p. 3609.

  18. Bandoli, G., Dolmella, A., Crociani, L., Antonaroli, S., and Crociani, B., Trans. Met. Chem., 2000, vol. 25, no. 1, p. 17.

    Article  CAS  Google Scholar 

  19. Watkins, S.E., Craig, D.C., and Colbran, S.B., Inorg. Chim. Acta, 2000, vol. 307, nos. 1–2, p. 134.

    Article  CAS  Google Scholar 

  20. Getty, A.D., and Goldberg, K.I., Organometallics, 2001, vol. 20, no. 12, p. 2545.

    Article  CAS  Google Scholar 

  21. Ohtaka, A., Kato, N., and Kurosawa, H., Organometallics, 2002, vol. 21, no. 25, p. 5464.

    Article  CAS  Google Scholar 

  22. Ankersmit, H.A., Loken, B.H., Kooijman, H., Spek, A.L., Vrieze, K., and Koten, G., Inorg. Chim. Acta, 1996, vol. 252, nos. 1–2, p. 141.

    Article  CAS  Google Scholar 

  23. Sanchez, G., Serrano, J.L., Lopez, C.M., Garcia, J., Perez, J., and Lopez, G., Inorg. Chim. Acta, 2000, vol. 306, no. 2, p. 168.

    Article  CAS  Google Scholar 

  24. Sanchez, G., Vives, J., Serrano, J.L., Perez, J., and Lopez, G., Inorg. Chim. Acta, 2002, vol. 328, no. 1, p. 74.

    Article  CAS  Google Scholar 

  25. Barbaro, P., Bianchini, C., Laschi, F., Midollini, S., Moneti, S., Scapacci, G., and Zanello, P., Inorg. Chem., 1994, vol. 33, no. 8, p. 1622.

    Article  CAS  Google Scholar 

  26. Lane, H.P., Watkinson, M., Bricklebank, N., McAuliffe, C.A., and Pritchard, R.G., Inorg. Chim. Acta, 1995, vol. 232, nos. 1–2, p. 145.

    Article  CAS  Google Scholar 

  27. Kbin, H.-F., Beck, R., Florke, U., and Haupt, H.-J., Eur. J. Inorg. Chem., 2002, no, 12, p. 3305.

  28. Del Zotto, A., Zangrando, E., Baratta, W., Felluga, A., Martinuzzi, P., and Rigo, P., Eur. J. Inorg. Chem., 2005, no. 23, p. 4707.

  29. Ainscough, E.W., Brodie, A.M., Burrell, A.K., and Kennedy, M.F., J. Organomet. Chem., 2000, vol. 609, nos. 1–2, p. 2.

    Article  CAS  Google Scholar 

  30. Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, no. 45, p. 11623.

    Article  CAS  Google Scholar 

  31. Sanchez, G., Serrano, J.L., Moral, M.A., Perez, J., Molins, E., and Lopez, G., Polyhedron, 1999, vol. 18, no. 23, p. 3057.

    Article  CAS  Google Scholar 

  32. Chen, X., Femia, F.J., Babich, J.W., and Zubieta, J., Inorg. Chim. Acta, 2001, vol. 315, no. 2, p. 147.

    Article  CAS  Google Scholar 

  33. Minkin, V.I., Olekhnovich, L.P., and Zhdanov, Yu.A., Molecular Design of Tautomeric Compounds, Boston: Kluwer, 1988.

    Google Scholar 

  34. Olekhnovich, L.P., and Zhdanov, Yu.A., Acc. Chem. Res., 1981, vol. 14, p. 210.

    Article  Google Scholar 

  35. Minkin, V.I., Pure Appl. Chem., 1989, vol. 61, p. 661.

    Article  CAS  Google Scholar 

  36. Minkin, V.I., Olekhnovich, L.P., and Zhdanov, Yu.A., Zh. Vses. Khim. O-va, 1977, vol. 22, p. 274.

    CAS  Google Scholar 

  37. Metelitsa, A.V., Burlov, A.S., Bezuglyi, S.O., Borodkina, I.G., Bren’, V.A., Garnovskii, A.D., and Minkin, V.I., Koord. Khim., 2006, vol. 32, no. 12, p. 894.

    Google Scholar 

  38. Katkova, M.A., Vitukhnovskii, A.G., and Bochkarev, M.N., Usp. Khim., 2005, vol. 74, no. 12, p. 1193.

    Google Scholar 

  39. Veinot, J.G.C., and Marks, T.J., Acc. Chem. Res., 2005, vol. 38, no. 8, p. 632.

    Article  CAS  Google Scholar 

  40. Organic Light-Emmiting Devices, Mueller, K., Schert, U. and Weinhein Eds., New York: Wiley-VCH, 2006, p. 426.

    Google Scholar 

  41. Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, no. 45, p. 11 623.

  42. Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648.

    Article  CAS  Google Scholar 

  43. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B., 1988, vol. 37, no. 2, p. 785.

    Article  CAS  Google Scholar 

  44. Granovsky, A.A., web-reference http://classic.chem.msu.su/gran/gamess/index.html .

  45. Zhurko, G.A., Chemcraft, ver. 1.5 trial, build 266. http://www.chemcraftprog.com/description.html .

  46. Cooper, M.K., Downes, J.M., Duckworth, P.A., and Tiekins, E.R.T., Aust. J. Chem., 1992, vol. 45, no. 9, p. 595.

    CAS  Google Scholar 

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Correspondence to S. A. Borodkin.

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Original Russian Text © L.D. Popov, S.A. Borodkin, I.N. Shcherbakov, Yu.N. Tkachenko, V.A. Kogan, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 4, pp. 586–593.

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Popov, L.D., Borodkin, S.A., Shcherbakov, I.N. et al. Synthesis, structure, and properties of new phosphorus Schiff bases. Russ J Gen Chem 78, 567–574 (2008). https://doi.org/10.1134/S1070363208040099

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