Synthesis, Structure, and Electron Density Distribution in Crystals of K2(L-Trp)2(H2O) (HTrp = Tryptophane)

N. A. Bondareva; Бондарева Н. А.; P. P. Purygin; Пурыгин П. П.; Yu. P. Zarubin; Зарубин Ю. П.; P. V.  Dorovatovskii; Дороватовский П. В.; A. A. Korlyukov; Корлюков А. А.; A. V. Vologzhanina; Вологжанина А. В.

doi:10.31857/S0132344X2260031X

Synthesis, Structure, and Electron Density Distribution in Crystals of K2(L-Trp)2(H2O) (HTrp = Tryptophane)

Authors: Bondareva N.A.¹, Purygin P.P.¹, Zarubin Y.P.¹, Dorovatovskii P.V.², Korlyukov A.A.³^,4, Vologzhanina A.V.⁴
Affiliations:
1. Samara National Research University, Samara, Russia
2. National Research Center Kurchatov Institute, Moscow, Russia
3. Pirogov Russian National Research Medical University, Moscow, Russia
4. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia
Issue: Vol 49, No 5 (2023)
Pages: 269-277
Section: Articles
URL: https://journals.rcsi.science/0132-344X/article/view/137287
DOI: https://doi.org/10.31857/S0132344X2260031X
EDN: https://elibrary.ru/FYZZTA
ID: 137287

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

The first salt of alkaline metal and L-tryptophane, K2(L-Trp)2(H2O) (I), is synthesized by the reaction of L-tryptophane (HTrp) with potassium hydroxide in an aqueous-alcohol solution. Compound I is characterized by IR and 1H NMR spectroscopy and X-ray diffraction (XRD) (CIF file CCDC no. 2184367). Compound I is found to have a layered structure due to the presence of the bridging water molecule and chelate-bridging anions. The quantum chemical calculations of the crystal structure (PBE, plane-wave basis set, 800 eV) is used to evaluate the strength of interactions of the potassium ion with the L-tryptophanate anion (depending on the coordination type) and the influence of the anion conformation on the strength of coordination, hydrophobic, and hydrophilic interactions.

Keywords

L-tryptophane, potassium salts, periodic quantum chemical calculations, crystal structure, Voronoi–Dirichlet polyhedra

References

Soldevila-Barreda J.J., Metzler-Nolte N. // Chem. Rev. 2019. V. 119. № 2. P. 829. https://doi.org/10.1021/acs.chemrev.8b00493
Saboury A.A. // J. Iran. Chem. Soc. 2006. V. 3. № 1. P. 1. https://doi.org/10.1007/BF03245784
Poursharifi M., Wlodarczyk M.T., Mieszawska A.J. // Inorganics. 2019. V. 7. № 1. P. 2. https://doi.org/10.3390/inorganics7010002
Palermo G., Spinello A., Saha A. et al. // Expert Opin. Drug Discov. 2021. V. 16. № 5. P. 497. https://doi.org/10.1080/17460441.2021.1851188
Vidossich P., Magistrato A. // Biomolecules. 2014. V. 4. № 3. P. 616. https://doi.org/10.3390/biom4030616
Palermo G., Magistrato A., Riedel T. et al. // ChemMedChem. 2016. V. 11. № 12. P. 1199. https://doi.org/10.1002/cmdc.201500478
Dey D., Basu S. // J. Lumin. 2011. V. 131. № 4. P. 732. https://doi.org/10.1016/j.jlumin.2010.11.027
Mosae Selvakumar P., Suresh E., Subramanian P.S. // Polyhedron. 2009. V. 28. № 2. P. 245. https://doi.org/10.1016/j.poly.2008.10.072
Maclaren J.K., Janiak C. // Inorg. Chim. Acta. 2012. V. 389. P. 183. https://doi.org/10.1016/j.ica.2012.03.010
Wang J., Xu X.-Y., Ma W.-X. et al. // Jiegou Huaxue. 2008. V. 27. P. 153.
Wang J., Xu X., Ma W. et al. // Acta Crystallogr. E. 2007. V. 63. № 11. P. m2867. https://doi.org/10.1107/S1600536807053421
Xie Y., Wu H.-H., Yong G.-P. et al. // Acta Crystallogr. E. 2006. V. 62. № 9. P. m2089. https://doi.org/10.1107/S1600536806030364
Mendiratta S., Usman M., Luo T.-T. et al. // Cryst. Growth Des. 2014. V. 14. № 4. P. 1572. https://doi.org/10.1021/cg401472k
Xiao D.-R., Zhang G.-J., Liu J.-L. et al. // Dalton Trans. 2011. V. 40. № 21. P. 5680. https://doi.org/10.1039/C1DT10262A
Mendiratta S., Tseng T.-W., Luo T.-T. et al. // Cryst. Growth Des. 2018. V. 18. № 5. P. 2672. https://doi.org/10.1021/acs.cgd.8b00012
Patra A.K., Bhowmick T., Ramakumar S. et al. // Dalton Trans. 2008. № 48. P. 6966. https://doi.org/10.1039/B802948B
Şenel P., İnci D., Aydın R. et al. // Appl. Organomet. Chem. 2019. V. 33. № 10. P. E5122. https://doi.org/10.1002/aoc.5122
Kumita H., Kato T., Jitsukawa K. et al. // Inorg. Chem. 2001. V. 40. № 16. P. 3936. https://doi.org/10.1021/ic000990p
Lazarenko V.A., Dorovatovskii P.V., Zubavichus Y.V. et al. // Crystals. 2017. V. 7. № 11. P. 325. https://doi.org/10.3390/cryst7110325
Svetogorov R.D., Dorovatovskii P.V., Lazarenko V.A. // Cryst. Res. Technol. 2020. V. 55. № 5. P. 1900184. https://doi.org/10.1002/crat.201900184
Kabsch W. // Acta Crystallogr. D. 2010. V. 66. № 2. P. 125. https://doi.org/10.1107/S0907444909047337
Evans P. // Acta Crystallogr. D. 2006. V. 62. № 1. P. 72. https://doi.org/10.1107/S0907444905036693
Sheldrick G.M. // Acta Crystallogr. A. 2015. V. 71. № 1. P. 3. https://doi.org/10.1107/S2053273314026370
Sheldrick G.M. // Acta Crystallogr. C. 2015. V. 71. № 1. P. 3. https://doi.org/10.1107/S2053229614024218
Dolomanov O.V., Bourhis L.J., Gildea R.J. et al. // J. A-ppl. Crystallogr. 2009. V. 42. № 2. P. 339. https://doi.org/10.1107/S0021889808042726
Peresypkina E.V., Blatov V.A. // Acta Crystallogr. B. 2000. V. 56. № 3. P. 501. https://doi.org/10.1107/S0108768199016675
Peresypkina E.V., Blatov V.A. // Acta Crystallogr. B. 2000. V. 56. № 6. P. 1035. https://doi.org/10.1107/S0108768100011824
Blatov V.A., Shevchenko A.P., Proserpio D.M. // Cryst. Growth Des. 2014. V. 14. № 7. P. 3576. https://doi.org/10.1021/cg500498k
Kresse G., Hafner J. // Phys. Rev. B. 1993. V. 47. № 1. P. 558. https://doi.org/10.1103/PhysRevB.47.558
Kresse G., Hafner J. // Phys. Rev. B. 1994. V. 49. № 20. P. 14251. https://doi.org/10.1103/PhysRevB.49.14251
Kresse G., Furthmüller J. // Phys. Rev. B. 1996. V. 54. № 16. P. 11169. https://doi.org/10.1103/PhysRevB.54.11169
Kresse G., Furthmüller J. // Comput. Mater. Sci. 1996. V. 6. № 1. P. 15. https://doi.org/10.1016/0927-0256(96)00008-0
Kresse G., Joubert D. // Phys. Rev. B. 1999. V. 59. № 3. P. 1758. https://doi.org/10.1103/PhysRevB.59.1758
Gonze X., Beuken J.-M., Caracas R. et al. // Comput. Mater. Sci. 2002. V. 25. № 3. P. 478. https://doi.org/10.1016/S0927-0256(02)00325-7
Tang W., Sanville E., Henkelman G. // J. Phys. Condens. Matter. 2009. V. 21. № 8. P. 084204. https://doi.org/10.1088/0953-8984/21/8/084204
Bader R.F.W. // Atoms in Molecules: A Quantum Theory, Clarendon Press, 1994. 438 p. https://books.google.ru/books?id=tyVpQgAACAAJ
Bader R.F.W. // Acc. Chem. Res. 1985. V. 18. № 1. P. 9. https://doi.org/10.1021/ar00109a003
Korlyukov A.A., Khrustalev V.N., Vologzhanina A.V. et al. // Acta Crystallogr. B. 2011. V. 67. № 4. P. 315. https://doi.org/10.1107/S0108768111022695
Vologzhanina A.V., Savchenkov A.V., Dmitrienko A.O. et al. // J. Phys. Chem. A. 2014. V. 118. № 41. P. 9745. https://doi.org/10.1021/jp507386j
Вологжанина А.В., Лысенко К.А. // Изв. АН. Сер. хим. 2013. Т. 62. № 8. С. 1786 (Vologzhanina A.V., Lyssenko K.A. // Russ. Chem. Bull. 2013. V. 62. № 8. P. 1786). https://doi.org/10.1007/s11172-013-0257-0
Serezhkin V.N., Serezhkina L.B., Vologzhanina A.V. // Acta Crystallogr. B. 2012. V. 68. № 3. P. 305. https://doi.org/10.1107/S0108768112014711
Serezhkin V.N., Savchenkov A.V. // Cryst. Growth Des. 2015. V. 15. № 6. P. 2878. https://doi.org/10.1021/acs.cgd.5b00326
Serezhkin V.N., Savchenkov A.V. // Cryst. Growth Des. 2020. V. 20. № 3. P. 1997. https://doi.org/10.1021/acs.cgd.9b01645
Serezhkin V.N., Savchenkov A.V. // CrystEngComm. 2021. V. 23. № 3. P. 562. https://doi.org/10.1039/D0CE01535K
Vologzhanina A.V. // Crystals. 2019. V. 9. № 9. P. 478. https://doi.org/10.3390/cryst9090478
Зорина-Тихонова Е.Н., Чистяков А.С., Кискин М.А. и др. // Коорд. химия. 2021. Т. 47. № 6. С. 373 (Zorina-Tikhonova E.N., Chistyakov A.S., Kiskin M.A. et al. // Russ. J. Coord. Chem. 2021. V. 47. № 6. P. 409). https://doi.org/10.1134/S1070328421060099
Karnoukhova V.A., Baranov V.V., Vologzhanina A.V. et al. // CrystEngComm. 2021. V. 23. № 24. P. 4312. https://doi.org/10.1039/D1CE00434D
Vologzhanina A.V., Ushakov I.E., Korlyukov A.A. // Int. J. Mol. Sci. 2020. V. 21. № 23. P. 8970. https://doi.org/10.3390/ijms21238970
Espinosa E., Molins E., Lecomte C. // Chem. Phys. Lett. 1998. V. 285. № 3. P. 170. https://doi.org/10.1016/S0009-2614(98)00036-0