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Amino-substitutedgem-diphosphonic acids: Dissociation mechanism and the structure of species in aqueous solutions

  • Physical Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

The mechanism of dissociation of amino-substitutedgem-diphosphonic acids R2N(CH2) n CR'(PO3H2)2 with different lengths of the alkylidene chain and different substituents at the N atom was studied by vibrational (IR, Raman) and NMR (1H,14N,31P) spectroscopy using data of conformational analysis (molecular mechanical) data. The important role of intramolecular H-bonds and cyclic solvates for the stabilization of various conformations and tautomeric forms of ions was demonstrated. The spectral data that allow one to consider thegem-diphosphonate group as a single acidic center were found.

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References

  1. F. H. Ebetino,Abstracts, XIVth Intern. Conference on Phosphorus C Chem. (XIVth-ICPC), Cincinnati, Ohio, 1998, B.1, p. LM1–1; G. RussellIbid., Abstracts, XIVth Intern. Conference on Phosphorus Chem. (XIVth-ICPC), Cincinnati, Ohio, 1998, B. 1, p. LMA: L. Widler, K. A. Jaeggi, J. R. Green, and F. H. Ebetino,Ibid., Abstracts, XIVth Intern. Conference on Phosphorus Chem. (XIVth-ICPC), Cincinnati, Ohio, 1998, B.1, p. LM1-3; H. Blum,Ibid., Abstracts, XIVth, Intern. Conference on Phosphorus Chem. (XIVth-ICPC), Cincinnati, Ohio, 1998, B.1, p. LF1-3; O. Aleksiuk, D. Z. Gabriel, D. Kantoci, W. J. Wechter, D. Borchardt, and F. H. Ebetino,Ibid. Abstracts, XIVth Intern. Conference on Phosphorus Chem. (XIVth-ICPC), Cincinnati, Ohio, 1998, B.1 p. PO5.

    Google Scholar 

  2. M. O. Lozinsky, A. L. Chuiko, P. Kafarski, I. Jasicka-Misiak, L. P. Filonenko, and A. N. Borisevich,Abstracts, XIVth Intern. Conference on Phosphorus Chem. (XIVth-ICPC), Cincinnati, Ohio, 1998, B.2, p. P148; P. Kafarski, B. Lejczak. G. Forlani, A. L. Chuiko, M. O. Lozinsky, I. Jasicka-Misiak, K. Czekala, and J. Lipok,Ibid., p. LH5-4.

    Google Scholar 

  3. E. I. Sinyavskaya,Koord. Khim., 1992,18, 899 [Sov. J. Coord. Chem., 1992,18, (Engl. Transl.)].

    CAS  Google Scholar 

  4. Calcium Disorders, Eds. D. Heath and S. J. Marx, Butterworth Scientific, London-Boston-Sydney-Wellington-Durban-Toronto, 1982.

    Google Scholar 

  5. S. V. Matveev, F. I. Bel'skii, A. G. Matveeva, A. Yu. Gukasova, Yu. M. Polikarpov, and M. I. Kabachnik,Izv. Akad. Nauk. Ser. Khim., 1998, 1784 [Russ. Chem. Bull., 1998,47, 1736 ((Engl. Transl.)].

    Google Scholar 

  6. M. I. Kabachnik, T. Ya. Medved', N. M. Dyatlova, Yu. M. Polikarpov, B. K. Shcherbakov, and F. I. Bel'skii,Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 433 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1978,27, 374 (Engl. Transl.)].

  7. M. I. Kabachnik. F. I. Bel'skii, M. P. Komarova, B. K. Shcherbakov, E. I. Matrosov, Yu. M. Polikarpov, N. M. Dyatlova, and T. Ya. Medved',Izv. Akad. Nauk SSSR, Ser. Khim., 1979, 1726 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979,28 (Engl. Transl.)]; b) T. A. Matkovskaya, L. S. Nikolaeva, B. K. Shcherbakov, A. M. Evseev, and N. M. Dyatlova,Zh. Neorg. Khim., 1987,32, 295 [J. Inorg. Chem. (USSR), 1987,32 (Engl. Transl.)]; c) K. B. Yatsimirskii, M. I. Kabachnik, E. I. Sinyavskaya, M. A. Konstantinovskaya, T. Ya. Medved', Yu. M. Polikarpov, and B. K. Shcherbakov,Zh. Neorg. Khim., 1980,25, 3326 [J. Inorg. Chem. (USSR) 1980,25 (Engl. Transl.)].

  8. M. I. Kabachnik and T. Ya Medved',Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1962, 2103 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 196211 (Engl. Transl.)].

  9. M. I. Kabachnik and E. S. Shepeleva,Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1953, 862 [Bull. Acad. Sci. SSSR, Div. Chem. Sci., 1953,2 (Engl. Transl.)].

  10. J. Dodonow and H. Medox,Chem. Ber., 1928,61, 907.

    Google Scholar 

  11. K. A. Petrov, F. L. Maklyaev, and N. K. Bliznyuk,Zh. Obshch. Khim., 1960,30, 1602 [J. Gen. Chem. USSR, 1960,30 (Engl. Transl.)].

    CAS  Google Scholar 

  12. T. Shedlovsky and D. A. Maclnnes,J. Am. Chem. Soc., 1937,59, 503.

    Article  CAS  Google Scholar 

  13. N. I. Voronezheva, Yu. V. Rudyak, N. M. Dyatlova, and A. I. Grigor'ev,Koord. Khim., 1980,6, 991 [Sov. J. Coord. Chem., 1980,6, (Engl. Transl.)].

    CAS  Google Scholar 

  14. G. C. Pimentel and A. L. McClellan,The Hydrogen Bond, San-Francisco-London, 1960.

  15. A. Yu. Kireeva, B. V. Zhadanov, and B. I. Bikhman,Trudy IREA [Collection of Works of IREA], 1972,34, 12 (in Russian).

    Google Scholar 

  16. E. Steger and J. Rehar,Z Anorg. Allg. Chem., 1965,336, 156.

    Article  CAS  Google Scholar 

  17. B. V. Zhadanov, I. A. Polyakova, N. V. Tsirul'nikov, T. M. Sushitskaya, and V. Ya. Temkina,Koord. Khim., 1979,5, 1614 [Sov. J. Coord. Chem., 1979,5 (Engl. Transl.)].

    CAS  Google Scholar 

  18. L. V. Nikitina, A. I. Grigor'ev, and N. M. Dyatlova,Zh. Obshch. Khim., 1974,44, 1598 [J. Gen. Chem. USSR, 1974,44 (Engl. Transl.)].

    CAS  Google Scholar 

  19. E. N. Rizkalla,Rev. Inorg. Chem., 1983,5, 223.

    CAS  Google Scholar 

  20. A. I. Grigor'ev,Dokl. Akad. Nauk SSSR, 1966,171, 136 [Dokl. Chem., 1966 (Engl. Transl.)].

    Google Scholar 

  21. K. W. F. Kohlrausch,Ramanspectren, Leipzig, 1943; (b) L. J. Bellamy,Advances. in Infrared Group Frequencies, Methuen & Co., Suffolk, 1968; (c) B. Schrader,Raman/Infrared Atlas of Organic Compounds, 2 ed., VCH-Verl.-Ges. Weinheim, 1989.

  22. T. G. Appleton, J. R. Hall, A. D. Harris, H. A. Kimlin, and I. J. McMahon,Aust. J. Chem., 1984,37, 1833.

    Article  CAS  Google Scholar 

  23. F. I. Bel'skii, I. B. Goryunova, P. V. Petrovskii, M. I. Kabachnik, and T. Ya. Medved',Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 103 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982,31 (Engl. Transl.)].

    Google Scholar 

  24. L. Maier,J. Organomet. Chem., 1979,178, 157; G. Hagele, M. Grozonka, H.-W. Kropp, J. Ollig, and H. Spiegl,Phosphorus, Sulfur, and Silicon, 1993,77, 85; Z. H. Kudzin, G. Andrijewski, and J. Drabowicz,Heteroatom Chem., 1994,5, 1; T. G. Appleton, J. R. Hall, and I. J. McMahon,Inorg. Chem., 1986,25, 726.

    Article  CAS  Google Scholar 

  25. R. J. Grabenstetter, O. T. Quimby, and T. J. Flautt,J. Phys. Chem., 1967,71, 4194.

    Article  CAS  Google Scholar 

  26. K. Moedritzer and R. R. Irani,J. Inorg. and Nucl. Chem., 1961,22, 297.

    Article  CAS  Google Scholar 

  27. G. Anderegg,Helv. Chim. Acta, 1965,48, 1712.

    Article  CAS  Google Scholar 

  28. E. N. Tsvetkov,Zh. Obshch. Khim., 1976,46, 2763 [J. Gen. Chem. USSR, 1976,46 (Engl. Transl.)].

    CAS  Google Scholar 

  29. I. G. Orlov, V. S. Markin, Yu. V. Moiseev, and U. I. Khurgin,Zh. Strukt. Khim. SSSR, 1966,7, 796 [J. Struct. Chem. USSR, 1966 (Engl. Transl.)].

    CAS  Google Scholar 

  30. Annual Reports on NMR Spectroscopy, V.18, Ed. G. A. Webb, Academic press, London, 1986, 761 p.

    Google Scholar 

  31. N. M. Dyatlova, V. Ya. Temkina, and K. I. Popov,Kompleksony i kompleksonary metallov [Complexones and Metal Complexonates]. Khimiya, Moscow, 1988, 422, 544.

    Google Scholar 

  32. J. W. Emsley, J. Feeney, and L. H. Sutcliffe,High Resolution Nuclear Magnetic Resonance Spectroscopy, V.2, Pergamon Press, Oxford-London-Edinburgh-New York-Paris-Frankfurt, 1966; (b) V.1

    Google Scholar 

  33. T. K. Leipert and J. H. Noggle,J. Am. Chem. Soc., 1975,97, 269.

    Article  CAS  Google Scholar 

  34. N. Naulet, D. Tome, and G. J. Martin,Org. Magnetic Res., 1983,21, 564.

    Article  CAS  Google Scholar 

  35. G. Gross, B. Kostizella, K. Shvarts, M. I. Kabachnik, F. I. Bel'skii, and M. Yu. Polikarpov,Zh. Obshch. Khim., 1990,60, 749 [J. Gen. Chem. USSR, 1990,60 (Engl. Transl.)].

    CAS  Google Scholar 

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    A. G. Matveeva, M. P. Pasechnik, P. V. Petrovskii, S. V. Matveev & S. A. Pisareva

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  1. A. G. Matveeva
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  2. M. P. Pasechnik
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  3. P. V. Petrovskii
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  4. S. V. Matveev
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Translated fromIzvestiya Akademii Nauk Seriya Khimicheskaya, No. 6, pp. 1051–1064, June, 2000.

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Matveeva, A.G., Pasechnik, M.P., Petrovskii, P.V. et al. Amino-substitutedgem-diphosphonic acids: Dissociation mechanism and the structure of species in aqueous solutions. Russ Chem Bull 49, 1045–1058 (2000). https://doi.org/10.1007/BF02494893

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