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Empirical Models of Stability of Crown Ether Complexes with Alkaline and Alkaline-Earth Metals in Selected Pure Solvents

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Abstract

An approach to predict the stability constants of coronates from the properties of solvents, cations, and crown ethers has been developed based on exploratory and neural network methods for mathematical modeling of equilibria in solutions. Exploratory (factor, cluster, discriminant, canonical, decision trees), regression, and neural network (supervised and Kohonen network) models of the stability of crown ethers (12С4, 13С4, 14С4, 15С4, 15С5, 18С6, 21С7, 24С8, B12C4, B15C5, CH15C5, CH18C6, DCH18C6, DCH21C7, DB18C6, DB21C7, DB24C8, DB27C9, and DB30C10) complexes with cations of alkali (Li+, Na+, K+, Cs+, Rb+) and alkaline-earth (Ca2+, Sr2+, Ba2+) metals in aqueous and non-aqueous (acetone, acetonitrile, dimethyl sulfoxide, methanol, pyridine, dimethylformamide, dioxane, propylene carbonate, 1,2-dichloroethane, and nitrobenzene) solutions have been developed according to the properties of solvents (diameter of solvent molecule, Kamlet–Taft parameter, Dimroth–Reichardt parameter, dielectric constant), crown ethers (Balaban topological index), and cations (cation diameter) at 298.15 K.

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REFERENCES

  1. Kamlet, M.J., Abboud, J.L.M., Abraham, M.H., and Taft, R.W.,J. Org. Chem., 1983, vol. 48, no. 17, p. 2877. https://doi.org/10.1021/jo00165a018

    Article  CAS  Google Scholar 

  2. Politzer, P. and Murray, J.S., Quantitative Approaches to Solute-Solvent Interactions. Modern Aspects of Electrochemistry, Vayenas, C., Ed., New York: Springer, 2005, no. 39, p. 1. https://doi.org/10.1007/978-0-387-31701-4_1

  3. Gao, H., Struble, T.J., Coley, C.W., Wang, Y., Green, W.H., and Jensen, K.F., ACS Cent. Sci., 2018, vol. 4, no. 11, p. 1465. https://doi.org/10.1021/acscentsci.8b00357

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Piccione, P.M., Baumeister, J., Salvesen, T., Flores, Y., Grosjean, Ch., Murudi, V., Shyadligeri, A., Lobanova, O., and Lothschütz, Ch., Org. Proc. Res. Dev., 2019, vol. 23, no. 5, p. 998. https://doi.org/10.1021/acs.oprd.9b00065

    Article  CAS  Google Scholar 

  5. Wang, H., Wang, X., Chen, G., Farajtabar, A., Zhao, H., and Li, X.,J. Chem. Eng. Data, 2019, vol. 64, no. 6, p. 2867. https://doi.org/10.1021/acs.jced.9b00243

    Article  CAS  Google Scholar 

  6. Wu, J., Wang, J., and Zhao, H., J. Chem. Eng. Data, 2019, vol. 64, no. 6, p. 2904. https://doi.org/10.1021/acs.jced.9b00320

    Article  CAS  Google Scholar 

  7. Qiu, J. and Albrecht, J., Org. Process Res. Dev., 2018, vol. 22, no. 7, p. 829. https://doi.org/10.1021/acs.oprd.8b00117

    Article  CAS  Google Scholar 

  8. Xu, R., Huang, C., and Xu, J., J. Chem. Eng. Data, 2019, vol. 64, no. 4, p. 1454. https://doi.org/10.1021/acs.jced.8b01051

    Article  CAS  Google Scholar 

  9. Li, W., Zhu, Ya., Wang, X., Zheng, M., Li, X., and Zhao, H.,J. Chem. Eng. Data, 2019, vol. 64, no. 2, p. 771. https://doi.org/10.1021/acs.jced.8b01014

    Article  CAS  Google Scholar 

  10. Chen, G., Liang, J., Han, J., and Zhao, H., J. Chem. Eng. Data, 2019, vol. 64, no. 1, p. 315. https://doi.org/10.1021/acs.jced.8b00811

    Article  CAS  Google Scholar 

  11. Laurence, C., Legros, J., Chantzis, A., Planchat, A., and Jacquemin, D., J. Phys. Chem. B, 2015, vol. 119, no. 7, p. 3174. https://doi.org/10.1021/jp512372c

    Article  CAS  PubMed  Google Scholar 

  12. Sanli, S., Altun, Y., and Guven, G., J. Chem. Eng. Data, 2014, vol. 59, no. 12, p. 4015. https://doi.org/10.1021/je500595w

    Article  CAS  Google Scholar 

  13. Bondarev, N.V., Russ. J. Gen. Chem., 2016, vol. 86, no. 6, p. 1221. https://doi.org/10.1134/S1070363216060025

    Article  CAS  Google Scholar 

  14. Bondarev, N.V., Russ. J. Gen. Chem., 2017, vol. 87, no. 2, p. 188. https://doi.org/10.1134/S1070363217020062

    Article  CAS  Google Scholar 

  15. Bondarev, N.V., Russ. J. Gen. Chem., 2019, vol. 89, no. 2, p. 281. https://doi.org/10.1134/S1070363219020191

    Article  CAS  Google Scholar 

  16. Bondarev, N.V., Russ. J. Gen. Chem., 2019, vol. 89, no. 7, p. 1438. https://doi.org/10.1134/S1070363219070144

    Article  CAS  Google Scholar 

  17. Nikulina, S.Yu., Chernova, A.A., Tret’yakova, S.S., and Nikulin, D.A., Ross. Kardiol. Zh., 2018, vol. 23, no. 10, p. 53. https://doi.org/10.15829/1560-4071-2018-10-53-58

    Article  Google Scholar 

  18. Tyutyunik, V.V., Bondaryev, M.V., Shevchenko, R.І., Chornogor, L.F., and Kalugіn, V.D., Tekhnogenno-ekologіchna bezpeka ta civіl'nij zahist., 2014, no. 7, p. 107.

    Google Scholar 

  19. Izatt, R.M., Bradshaw, J.S., Nielsen, S.A., Lamb, J.D., Christensen, J.J., and Sen, D., Chem. Rev., 1985, vol. 85, no. 4, p. 271. https://doi.org/10.1021/cr00068a003

    Article  CAS  Google Scholar 

  20. Frensdorff, H.K., J. Am. Chem. Soc., 1971, vol. 93, no. 3, p. 600. https://doi.org/10.1021/ja00732a007

    Article  CAS  Google Scholar 

  21. Pedersen, C.J. and Frensdorff, H.K., Angew Chem. Int. Ed., 1972, vol. 11, no. 1, p. 16. https://doi.org/10.1002/anie.197200161

    Article  CAS  Google Scholar 

  22. Izatt, R.M., Terry, R.E., Haymore, B.L., Hansen, L.D., Dalley, N.K., Avondet, A.G., and Christensen, J.J., J. Am. Chem. Soc., 1976, vol. 98, no. 24, p. 7620. https://doi.org/10.1021/ja00440a028

    Article  CAS  Google Scholar 

  23. Høiland, H., Ringseth, J.A., and Brun, T.S., J. Solut. Chem., 1979, vol. 8, no. 11, p. 779. https://doi.org/10.1007/bf00648577

    Article  Google Scholar 

  24. Smetana, A.J., Popov, A.I., J. Solut. Chem., 1980, vol. 9, no. 3, p. 183. https://doi.org/10.1007/bf00648325

    Article  CAS  Google Scholar 

  25. Lin, J.D. and Popov, A.I., J. Am. Chem. Soc., 1981, vol. 103, no. 13, p. 3773. https://doi.org/10.1021/ja00403a026

    Article  CAS  Google Scholar 

  26. Host Guest Complex Chemistry III, Vögtle, F. and Weber, E., Eds., Berlin; Heidelberg: Springer, 1984, vol. 121, p. 1. https://doi.org/10.1007/3-540-12821-2_1

  27. Stover, F.S., J. Chromatogr. (A), 1984, vol. 298, p. 203. https://doi.org/10.1016/s0021-9673(01)92714-1

    Article  CAS  Google Scholar 

  28. Samec, Z. and Papoff, P., Anal. Chem., 1990, vol. 62, no. 10, p. 1010. https://doi.org/10.1021/ac00209a009

    Article  CAS  Google Scholar 

  29. Gokel, G.W., Leevy, W.M., and Weber, M.E., Chem. Rev., 2004, vol. 104, no. 5, p. 2723. https://doi.org/10.1021/cr020080k

    Article  CAS  PubMed  Google Scholar 

  30. Bondarev, N.V., Russ. J. Gen. Chem., 2006, vol. 76, no. 1, p. 11. https://doi.org/10.1134/S1070363219020191

    Article  CAS  Google Scholar 

  31. Gokel, G.W., Goli, D.M., Minganti, C., and Echegoyen, L., J. Am. Chem. Soc., 1983, vol. 105, no. 23, p. 6786. https://doi.org/10.1021/ja00361a003

    Article  CAS  Google Scholar 

  32. Inoue, Y., Hakushi, T., Liu, Y., and Tong, L.H., J. Org. Chem., 1993, vol. 58, no. 20, p. 5411. https://doi.org/10.1021/jo00072a024

    Article  CAS  Google Scholar 

  33. Lamb, J.D., Izatt, R.M., Swain, C.S., and Christensen, J.J.,J. Am. Chem. Soc., 1980, vol. 102, no. 2, p. 475. https://doi.org/10.1021/ja00522a005

    Article  CAS  Google Scholar 

  34. Haymore, B.L., Lamb, J.D., Izatt, R.M., and Christensen, J.J.,Inorg. Chem., 1982, vol. 21, no. 4, p. 1598. https://doi.org/10.1021/ic00134a065

    Article  CAS  Google Scholar 

  35. Bradshaw, J.S. and Izatt, R.M., Acc. Chem. Res., 1997, vol. 30, no. 8, p. 338. https://doi.org/10.1021/ar950211m

    Article  CAS  Google Scholar 

  36. Shamsipur, M. and Popov, A.I., J. Am. Chem. Soc., 1979, vol. 101, no. 15, p. 4051. https://doi.org/10.1021/ja00509a005

    Article  CAS  Google Scholar 

  37. Hopkins, H.P. and Norman, A.B., J. Phys. Chem., 1980, vol. 84, no. 3, p. 309. https://doi.org/10.1021/j100440a019

    Article  CAS  Google Scholar 

  38. Buschmann, H.-J., J. Sol. Chem., 1988, vol. 17, no. 3, p. 277. https://doi.org/10.1007/bf00646180

    Article  CAS  Google Scholar 

  39. El’tsov, S.V., Doroshenko, A.O., Bondarev, N.V., Russ. J. Inorg. Chem., 1999, vol. 44, no. 2, p. 284.

    Google Scholar 

  40. Marcus, Y., The Properties of Solvents, Chichester: John Wiley & Sons, 1999, vol. 4. 399 p.

  41. Shannon, R.D. and Prewitt, C.T., Acta Crystallogr. (B), 1969, vol. 25, no. 5, p. 925. https://doi.org/10.1107/s0567740869003220

    Article  CAS  Google Scholar 

  42. Shannon, R.D. and Prewitt, C.T., J. Inorg. Nucl. Chem., 1970, vol. 32, no. 5, p. 1427. https://doi.org/10.1016/0022-1902(70)80629-7

    Article  CAS  Google Scholar 

  43. Bugaenko, L.T., Ryabykh, S.M., and Bugaenko, A.L., Moscow. Univ. Chem. Bull., 2008, no. 6, p. 303. https://doi.org/10.3103/s0027131408060011

    Article  Google Scholar 

  44. Balaban, A.T., J. Pure Appl. Chem., 1983, vol. 55, no. 2, p. 199. https://doi.org/10.1351/pac198855020199

    Article  CAS  Google Scholar 

  45. Stankevich, M.I., Stankevich, I.V., and Zefirov, N.S., Usp. Khim., 1988, vol. 58, no. 3, p. 337.

    Google Scholar 

  46. Xing, R., Zhou, B., and Graovac, A., Ars Combin., 2012, vol. 104, p. 211.

    Google Scholar 

  47. Vasilyev, A. and Stevanovíc, D., MATCH Commun. Math. Comput. Chem., 2014, vol. 71, p. 657.

    Google Scholar 

  48. Reichardt, C., Solvent Effects in Organic Chemistry, Weinheim: Verlag Chemie, 1978.

  49. Borovikov, V., STATISTICA. Iskusstvo analiza dannykh na komp’yutere: Dlya professionalov (The Art of Computer Data Analysis: For Professionals), St. Petersburg: Piter, 2003.

  50. Paklin, N.B. and Oreshkov, V.I., Biznes-analitika: ot dannykh k znaniyam (Business Intelligence: From Data to Knowledge), St. Petersburg: Piter, 2009.

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ACKNOWLEDGMENTS

Author is grateful to IT specialist D.A. Kozlov for the assistance in the processing of the raw data on the coronates stability constants and calculation of the topology indices of the crown ethers.

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  1. V.N. Karazin Kharkov National University, 61022, Kharkov, Ukraine

    N. V. Bondarev

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Bondarev, N.V. Empirical Models of Stability of Crown Ether Complexes with Alkaline and Alkaline-Earth Metals in Selected Pure Solvents. Russ J Gen Chem 90, 1040–1050 (2020). https://doi.org/10.1134/S1070363220060171

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