Skip to main content
SpringerLink
Log in

Calorimetric and structural studies of organic compound of tris(pentafluorophenyl)-4-pyridylethylgermane

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

In the present research, the temperature dependence of heat capacity of tris(pentafluorophenyl)-4-pyridylethylgermane (C6F5)3Ge–CH2–CH2–C5H4N was studied by precise adiabatic vacuum calorimetry and differential scanning calorimetry over the temperature range from 6 to 450 K. The temperature and enthalpy of fusion of tris(pentafluorophenyl)-4-pyridylethylgermane and the total mole fraction of impurities have been determined. The thermal stability of the sample was investigated by thermogravimetric analysis. The experimental data were used to calculate the standard thermodynamic functions: heat capacity, enthalpy, entropy, and the Gibbs energy over the range from T → 0 to 420 K for crystalline and liquid states. For the compound under study, the standard entropy of formation in the crystalline state was calculated at T = 298.15 K. In addition, the structure of the investigated compound was established, and corresponding structural parameters were determined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Chambers RD. Fluorine in organic chemistry. Oxford: Blackwell Publishing Ltd.; 2004.

    Book  Google Scholar 

  2. Bardin VV. Synthesis of bis(pentafluorophenyl)phenylhalogenogermanes and bis(pentafluorophenyl)dihalogenogermanes, (C6F5)2GeXY (X = Ph, Y = Br, Cl; X = Y = F, Cl, Br). J Organomet Chem. 2016;822:46–52.

    Article  CAS  Google Scholar 

  3. Song B, Yang S, Zhong H, Jin L, Hu D, Liu G. Synthesis and bioactivity of 2-cyanoacrylates containing a trifluoromethylphenyl moiety. J Fluor Chem. 2005;126:7–92.

    Article  CAS  Google Scholar 

  4. Banks RE, Smart BE, Tatlow JC. Organofluorine. Chemistry principles and commercial applications. New York: Plenum; 1994.

    Book  Google Scholar 

  5. Kissa E. Fluorinated surfactants: synthesis, properties, applications. Surfactant Science Series, Vol. 50. New York: Marcel Dekker; 1994.

    Google Scholar 

  6. Kronberg B, Holmberg K, Lindman B. Surface chemistry of surfactants and polymers. Chichester: Wiley; 2014.

    Book  Google Scholar 

  7. Guo W, Brown TA, Fung BM. Micelles and aggregates of fluorinated surfactants. J Phys Chem. 1991;95:1829–36.

    Article  CAS  Google Scholar 

  8. Magueur G, Crousse B, Charneau S, Grellier P, Begue JP, Bonnet-Delpon D. Fluoroartemisinin: trifluoromethyl analogues of artemether and artesunate. J Med Chem. 2004;47:2694–9.

    Article  CAS  PubMed  Google Scholar 

  9. Gamage SA, Spicer JA, Rewcastle GW, Milton J, Sohal S, Dangerfield W, Mistry P, Vicker N, Charlton PA, Denny WA. Structure-activity relationships for pyrido-, imidazo-, pyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerase-targeted anticancer agents. J Med Chem. 2002;45:740–3.

    Article  CAS  PubMed  Google Scholar 

  10. Abdou IM, Saleh AM, Zohdi HF. Synthesis and antitumor activity of 5-trifluoromethyl-2,4- dihydropyrazol-3-one nucleosides. Molecules. 2004;9:109–16.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Filler R. Biochemistry involving carbon–fluorine bonds. Washington: American Chemical Society; 1976.

    Book  Google Scholar 

  12. Bhamaria RP, Bellare RA, Deliwala CV. In intro effect of 1-acyl-4-alkyl-(oraryl)-thiosemicarbazides 1-(5-chlorosalicylidine)-4-alkyl-(oraryl)-thiosemicarbazones and some hydrazones of 5-chlorosalicylaldehyde against pathogenic bacteria including mycobacterium tuberculosis (H37Rv). Indian J Exp Biol. 1968;6:62–3.

    CAS  PubMed  Google Scholar 

  13. Fujiwara T, Takeuchi Y. Synthesis, reactions, and applications of fluorine-containing multifunctional carbon compounds. J Fluor Chem. 2005;126:941–55.

    Article  CAS  Google Scholar 

  14. Salunkhe NG. Green synthesis, characterization and biological evaluation of some triazole and thiadiazole. J Curr Chem Pharm Sci. 2012;2(2):100–6.

    CAS  Google Scholar 

  15. Ishikawa N. Synthesis function of fluorinated compounds. CMC: Tokyo; 1987.

    Google Scholar 

  16. Zamyshlyaeva OG, Lapteva OS, Blinova LS, Fukin GK. Tris-(pentafluorophenyl)-4-pyridylethylgermane and method for production thereof. Patent RU 2591958 C1; 2016.

  17. Gasilova ER, Saprykina NN, Zamyshlyayeva OG, Semchikov YuD, Bochkarev MN. Hyperbranched perfluorinated poly(phenylenegermanes) obtained by polycondensation of A2B2 and AB3 monomers. J Phys Org Chem. 2010;23:1099–107.

    Article  CAS  Google Scholar 

  18. SAINT. Data reduction and correction program., v. 8.34A and v.8.37A, Bruker AXS, Madison, Wisconsin, USA. 2014.

  19. Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015;C71:3–8.

    Google Scholar 

  20. Sheldrick GM. SADABS 2012/1, Bruker AXS area detector scaling and absorption correction. Madison: Bruker AXS; 1998.

    Google Scholar 

  21. Piskunov AV, Aivaz’yan IA, Poddel’sky AI, Fukin GK, Baranov EV, Cherkasov VK, Abakumov GA. New germanium complexes containing ligands based on 4,6-di-tert-butyl-N-(2,6-diisopropylphenyl)-o-iminobenzoquinone in different redox states. Eur J Inorg Chem. 2008;8:1435–44.

    Article  CAS  Google Scholar 

  22. Uhl W, Bohnemann J, Kappelt B, Malessa K, Rohling M, Tannert J, Layh M, Hepp A. Hydrometallation (M = Al, Ga) of silicon- and germanium-centred oligoalkynes. Z Naturforsch. 2014;69b:1333–47.

    Article  Google Scholar 

  23. Rohwer H, Dillen J. Deviation from tetrahedral geometry in Me2GeCl2: crystal structure of a model compound and insight from ab initio calculations. Inorg Chem. 2002;41:4167–72.

    Article  CAS  PubMed  Google Scholar 

  24. Batsanov SS. Van der Waals radii of elements. Inorg Mater. 2001;37:871–85.

    Article  CAS  Google Scholar 

  25. Varushchenko RM, Druzhinina AI, Sorkin EL. Low-temperature heat capacity of 1-bromoperfluorooctane. J Chem Thermodyn. 1997;29:623–7.

    Article  CAS  Google Scholar 

  26. Malyshev VM, Milner GA, Sorkin EL, Shibakin VF. Automatic low-temperature calorimeter. Prib Tekh Eksp. 1985;6:195–7 [in Russian].

    Google Scholar 

  27. Höhne GWH, Hemminger WF, Flammersheim H-J. Differential scanning calorimetry. 2nd ed. Heidelberg: Springer; 2003.

    Book  Google Scholar 

  28. Drebushchak VA. Calibration coefficients of heat-flow DSC. Part II. Optimal calibration procedure. J Therm Anal Calorim. 2005;79:213–8.

    Article  CAS  Google Scholar 

  29. Aleksandrov YuI. Tochnaya Kriometriya Organicheskih Veshestv. Leningrad: Khimiya; 1975.

    Google Scholar 

  30. Rabinovich IB, Nistratov VP, Telnoy VI, Sheiman MS. Thermochemical and thermodynamic properties of organometallic compounds. New York: Begell House Inc., Publishers; 1999.

    Google Scholar 

  31. Sologubov SS, Markin AV, Smirnova NN, Rybakova YuA, Novozhilova NA, Tatarinova EA, Muzafarov AM. Calorimetric study of carbosilane dendrimers of the third and sixth generations with phenylethyl terminal groups. J Therm Anal Calorim. 2016;125:595–606.

    Article  CAS  Google Scholar 

  32. McCullough JP, Scott DW. Calorimetry of non-reacting systems. London: Butterworth; 1968.

    Google Scholar 

  33. Chase MW Jr. NIST-JANAF thermochemical tables, 4th ed. J Phys Chem Ref Data Monogr. 1998;9:1951. http://webbook.nist.gov/chemistry/. Accessed 5 July 2018.

  34. Cox JD, Wagman DD, Medvedev VA. CODATA key values for thermodynamics. New York; 1989. http://webbook.nist.gov/chemistry/. Accessed 5 July 2018.

Download references

Acknowledgments

This work was performed with the financial support of the Ministry of Education and Science of the Russian Federation (Contracts Nos. 4.6138.2017/6.7 and 4.5706.2017/8.9) and the Russian State Assignment (Theme No. 44.2, Reg. No. AAAA-A16-116122110053-1). The elemental analysis was conducted based on equipment of the Common Use Center « New Materials and Resource-saving Technologies» of the Research Institute for Chemistry of National Research Lobachevsky State University of Nizhny Novgorod.

Author information

Authors and Affiliations

  1. National Research Lobachevsky State University of Nizhny Novgorod, 23/5 Gagarin Ave, Nizhny Novgorod, Russian Federation, 603950

    O. G. Zamyshlyayeva, A. V. Markin, N. N. Smirnova, S. S. Sologubov & L. S. Blinova

  2. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, 49 Tropinin St, Nizhny Novgorod, Russian Federation, 603950

    A. S. Shavyrin, R. V. Rumyantsev & G. K. Fukin

Authors
  1. O. G. Zamyshlyayeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Markin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. N. Smirnova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. S. Sologubov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. S. Blinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. S. Shavyrin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. R. V. Rumyantsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. G. K. Fukin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Markin.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zamyshlyayeva, O.G., Markin, A.V., Smirnova, N.N. et al. Calorimetric and structural studies of organic compound of tris(pentafluorophenyl)-4-pyridylethylgermane. J Therm Anal Calorim 136, 1227–1236 (2019). https://doi.org/10.1007/s10973-018-7786-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-018-7786-6

Keywords

Search

Navigation