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Formation of Diazepam–Lanthanides(III) Complexes in the 50–50 Volume % Ethanol–Water Solvent System and Study of the Effect of Temperature on the Complex Formation Constants

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Abstract

Diazepam (7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one) is an important derivative of the 1,4-benzodiazepine compound commercially distributed as Valium. The complex formation constants of diazepam with some light lanthanide(III) metal ions have been studied by potentiometric measurements. All titrations were performed in 50–50% (volume/volume) ethanol–water solvent mixtures at constant ionic strength (0.10 mol⋅dm−3). The ionic strength was maintained by using sodium perchlorate. The complex formation constants were determined at 25.00, 35.00 and 45.00 °C. With increasing temperature, a decrease was observed in the protonation constant (pK) of diazepam.

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References

  1. Moros, J., Garrigues, S., Guardia, M.: Quality control Fourier transform infrared determination of pharmaceuticals. J. Pharm. Biomed. Anal. 43, 1277–1282 (2007)

    Article  CAS  Google Scholar 

  2. Correia dos Santos, M.M., Famila, V., Simoes Goncalves, M.L.: Copper–psychoactive drug complexes: a voltammetric approach to complexation by 1,4-benzodiazepines. Anal. Biochem. 303, 111–119 (2002)

    Article  Google Scholar 

  3. El-Hawary, W.F., Issa, Y.M., Talat, A.: Spectrophotometric determination of diazepam in pure form, tablets and ampoules. Int. J. Biomed. Sci. 3, 50–55 (2007)

    CAS  Google Scholar 

  4. Guo, W., Lin, H., Liu, L., Song, J.: Polarographic determination of diazepam with its parallel catalytic wave in the presence of persulfate. J. Pharm. Biomed. Anal. 34, 1137–1144 (2004)

    Article  CAS  Google Scholar 

  5. Mosset, A., Tuchagues, J.P., Bonnet, J.J., Haran, R., Sharrock, P.: Solution and solid-state structural study of the copper(II) complex of diazepam. Inorg. Chem. 19, 290–294 (1980)

    Article  CAS  Google Scholar 

  6. Vinkovic, V., Raza, Z., Sunjic, V.: 13C NMR and IR evidence for the two types of copper(I) and (II) complexes with 5-pyrido-1,4-benzodiazepin-2-ones. Spectrosc. Lett. 27, 269–279 (1994)

    Article  CAS  Google Scholar 

  7. Cinellu, M.A., Stoccoro, S., Minghetti, G., Bandini, A.L., Demartin, F.: Mono and dinuclear gold(I) complexes with neutral and deprotonated 1,4-benzodiazepin-2-ones. Crystal and molecular structure of (L–H) Au(PPh3)⋅Et2O, where L = 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one, nitrazepam. Inorg. Chim. Acta 168, 33–41 (1990)

    Article  CAS  Google Scholar 

  8. Preti, C., Tosi, G.: A novel series of palladium(II) and platinum(II) complexes with 1,4-benzodiazepines as ligands. J. Coord. Chem. 8, 223–229 (1979)

    Article  CAS  Google Scholar 

  9. Preti, C., Tosi, G.: Syntheses and spectroscopic studies on group IIB metal 1,4-benzodiazepine complexes. Transit. Metal Chem. 3, 246–250 (1978)

    Article  CAS  Google Scholar 

  10. Wittwer, J.D.: Application of high pressure liquid chromatography to the forensic analysis of several benzodiazepines. J. Liq. Chromatogr. Relat. Technol. 3, 1713–1724 (1980)

    Article  CAS  Google Scholar 

  11. Perez-Lozano, P., Garcia-Montoya, E., Orriols, A., Minarro, M., Tico, J.R., Sune-Negre, J.M.: Development and validation of a new HPLC analytical method for the determination of alprazolam in tablets. J. Pharm. Biomed. Anal. 34, 979–987 (2004)

    Article  CAS  Google Scholar 

  12. Nedved, M.L., Habibi-Goudarzi, S., Ganem, B., Henion, J.D.: Characterization of benzodiazepine “combinatorial” chemical libraries by on-line immunoaffinity extraction, coupled column HPLC–ion spray mass spectrometry–tandem mass spectrometry. Anal. Chem. 68, 4228–4236 (1996)

    Article  CAS  Google Scholar 

  13. Kleinschnitz, M., Herderich, M., Schreier, P.: Determination of 1,4-benzodiazepines by high-performance liquid chromatography–electrospray tandem mass spectrometry. J. Chromatogr. B 676, 61–67 (1996)

    Article  CAS  Google Scholar 

  14. Frankiln-Smyth, W., Grooves, J.A.: A polarographic study of the hydrolysis of 1,4-benzodiazepines and its analytical applications. Anal. Chem. Acta 134, 227–238 (1983)

    Article  Google Scholar 

  15. Feher, S., Horvai, G., Nagy, G., Niegreisz, Z., Toth, K., Pungor, E.: A polarographic and spectrophotometric routine analyzer for assaying content uniformity in pharmaceutical quality control. Anal. Chem. Acta 145, 41–50 (1983)

    Article  CAS  Google Scholar 

  16. Sioufi, A., Dubois, J.P.: Chromatography of benzodiazepines. J. Chromatogr., B, Biomed. Sci. Appl. 531, 459–480 (1990)

    Article  CAS  Google Scholar 

  17. Berrueta, L.A., Gallo, B., Vicente, F.: Biopharmacological data and high-performance liquid chromatographic analysis of 1,4-benzodiazepines in biological fluids: a review. J. Pharm. Biomed. Anal. 10, 109–136 (1992)

    Article  CAS  Google Scholar 

  18. Pietrogrando, A., Guerrato, A., Fini, G.D.: Automatic potentiometric micro-determination of basic nitrogen in organic compounds. Analyst 109, 1541–1543 (1984)

    Article  Google Scholar 

  19. Salem, A.A., Barsoum, B.N., Izake, E.L.: Potentiometric determination of diazepam, bromazepam and clonazepam using solid contact ion-selective electrodes. Anal. Chim. Acta 498, 79–91 (2003)

    Article  CAS  Google Scholar 

  20. Correia dos Santos, M.M., Famila, V., Simoes Goncalves, M.L.: A voltammetric study of the complexation of copper by the psychoactive compounds 1,4-benzodiazepines. Electroanalysis 12, 216–222 (2000)

    Article  Google Scholar 

  21. Irving, H., Rossotti, H.: Methods for computing successive stability constants from experimental formation curves. J. Chem. Soc. 3397–3405 (1953)

  22. Irving, H., Rossotti, H.: The calculation of formation curves of metal complexes from pH titration curves in mixed solvents. J. Chem. Soc. 2904–2910 (1954)

  23. Irving, H., Rossotti, H.: The stabilities of some metal complexes of 8-hydroxyquinoline and related substances. J. Chem. Soc. 2910–2918 (1954)

  24. Hagel, R.B., Debesis, E.M.: The non-aqueous reactions of some 1,4-benzodiazepines. Anal. Chim. Acta 78, 439–450 (1975)

    Article  CAS  Google Scholar 

  25. Perez, J., Riera, V., Rodrıguez, A., Miguel, D.: Synthesis and structure of the first ruthenated benzodiazepines. Organometallics 21, 5437–5438 (2002)

    Article  CAS  Google Scholar 

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Acknowledgement

The authors thank the late Prof. V.G. Dongre, Department of Chemistry, University of Mumbai for his precious guidance.

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Authors and Affiliations

  1. Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz (East), Mumbai, 400 098, Maharashtra, India

    Gunaji S. Bayes, Sambhaji S. Raut, Vishwanath R. Patil & Rama S. Lokhande

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  1. Gunaji S. Bayes
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  2. Sambhaji S. Raut
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  3. Vishwanath R. Patil
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  4. Rama S. Lokhande
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Correspondence to Vishwanath R. Patil.

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Bayes, G.S., Raut, S.S., Patil, V.R. et al. Formation of Diazepam–Lanthanides(III) Complexes in the 50–50 Volume % Ethanol–Water Solvent System and Study of the Effect of Temperature on the Complex Formation Constants. J Solution Chem 41, 241–248 (2012). https://doi.org/10.1007/s10953-012-9798-3

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