Skip to main content
Log in

L-Cysteine Nitrates

  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

The formation of salts in the L-cysteine–HNO3–H2O system was studied yielding three representatives as single crystals: anhydrous L-cysteinium nitrate (L-CysH)NO3 (I) and two new salts (L-CysH⋯L-Cys)NO3 (II) and (L-CysH⋯L-Cys)NO3∙0.5H2O (III) with the dimeric (L-CysH⋯L-Cys) cation. (I), (II) and (III) crystallize in space groups P212121, P21 and I2, respectively. Dimeric cations in (II) and (III) were formed by very short O–H⋯O hydrogen bonds with R(O⋯O) distances of 2.440(2) Å and 2.4352(17) Å, respectively. Infrared and Raman spectra of (IIII) were registered and discussed in relation to crystal structures. Characteristics of dimeric cations are compared with those in the previously obtained compounds of L-CysH(L-CysH⋯L-Cys)F(F⋯HF), (L-CysH⋯L-Cys)Cl, (L-CysH⋯L-Cys)Br and (L-CysH⋯L-Cys)I·0.5H2O.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

REFERENCES

  1. M. Fleck and A. M. Petrosyan. Salts of Amino Acids: Crystallization, Structure and Properties. Dordrecht, Netherlands: Springer, 2014. https://doi.org/10.1007/978-3-319-06299-0

    Book  Google Scholar 

  2. R. Pepinsky, K. Vedam, S. Hoshino, and Y. Okaya. Ferroelectricity in di-glycine nitrate (NH2CH2COOH)2·HNO3. Phys. Rev., 1958, 111(2), 430-432. https://doi.org/10.1103/physrev.111.430

    Article  CAS  Google Scholar 

  3. A. M. Petrosyan, V. V. Ghazaryan, G. Giester, M. Fleck, Z. Tylczyński, and M. Wiesner. Halogenides of dimethylglycine in comparison with respective salts of glycine, sarcosine and betaine. J. Mol. Struct., 2018, 1158, 106-121. https://doi.org/10.1016/j.molstruc.2018.01.017

    Article  CAS  Google Scholar 

  4. M. Szafrański, Z. Tylczyński, M. Wiesner, P. Czarnecki, V. V. Ghazaryan, and A. M. Petrosyan. Above-room-temperature ferroelectricity and piezoelectric activity of dimethylglycinium-dimethylglycine chloride. Mater. Des., 2022, 220, 110893. https://doi.org/10.1016/j.matdes.2022.110893

    Article  CAS  Google Scholar 

  5. B. T. Matthias, C. E. Miller, and J. P. Remeika. Ferroelectricity of glycine sulfate. Phys. Rev., 1956, 104(3), 849/850. https://doi.org/10.1103/physrev.104.849.2

    Article  CAS  Google Scholar 

  6. V. V. Ghazaryan, M. Fleck, and A. M. Petrosyan. New chemical analogs of triglycine sulfate. J. Cryst. Growth, 2014, 401, 857-862. https://doi.org/10.1016/j.jcrysgro.2013.11.054

    Article  CAS  Google Scholar 

  7. R. R. Ayyar and R. Srinivasan. Crystal structure of L(+)-cysteine hydrochloride monohydrate. Curr. Sci., 1965, 34(15), 449/450.

  8. R. R. Ayyar. Crystal structure of L(+)-cysteine hydrochloride monohydrate. Z. Kristalogr. - Cryst. Mater., 1968, 126(1-6), 227-239. https://doi.org/10.1524/zkri.1968.126.16.227

    Article  Google Scholar 

  9. R. P. Chapman and D. L. Bryce. A high-field solid-state 35/37Cl NMR and quantum chemical investigation of the chlorine quadrupolar and chemical shift tensors in amino acid hydrochlorides. Phys. Chem. Chem. Phys., 2007, 9(47), 6219. https://doi.org/10.1039/b712688c

    Article  CAS  PubMed  Google Scholar 

  10. G. Bhagavannarayana, S. Kumar, M. Shakir, S. K. Kushawaha, K. K. Maurya, R. Malhotra, and K. R. Rao. Unidirectional growth of L-cysteine hydrochloride monohydrate: first time observation as nonlinear optical material and its characterization. J. Appl. Crystallogr., 2010, 43(4), 710-715. https://doi.org/10.1107/s0021889810016870

    Article  CAS  Google Scholar 

  11. J. F. Silva Jr., G. D. S. Souza, C. L. Lima, P. T. C. Freire, and G. S. Pinheiro. Vibrational properties of L-cysteine hydrochloride monohydrate crystal under high-pressure. Vib. Spectrosc., 2018, 98, 92-97. https://doi.org/10.1016/j.vibspec.2018.07.003

    Article  CAS  Google Scholar 

  12. Y. Shan and S. D. Huang. Crystal structure of L-cysteine L-tartarte monohydrate, C7H15NO9S. Z. Kristallogr. - New Cryst. Struct., 1999, 214(1), 41/42. https://doi.org/10.1515/ncrs-1999-0124

    Article  CAS  Google Scholar 

  13. S. A. Martin Britto Dhas and S. Natarajan. Growth and characterization of two new NLO materials from the amino acid family: L-histidine nitrate and L-cysteine tartrate monohydrate. Opt. Commun., 2008, 281(3), 457-462. https://doi.org/10.1016/j.optcom.2007.09.049

    Article  CAS  Google Scholar 

  14. V. S. Minkov and E. V. Boldyreva. L-Cysteinium semioxalate. Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2008, 64(6), o344-o348. https://doi.org/10.1107/s0108270108014911

    Article  CAS  PubMed  Google Scholar 

  15. V. S. Minkov and E. V. Boldyreva. L-Cysteinium semioxalate: a new monoclinic polymorph or a hydrate? Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2011, 67(4), o139-o142. https://doi.org/10.1107/s0108270111009760

    Article  CAS  PubMed  Google Scholar 

  16. H. Schmid. Addition Compounds of Amino Acids and Hydrofluoric Acid or Soluble Fluorides, and Method of Preparing the Same. US Patent 3413326, 1968.

  17. V. S. Minkov, V. V. Ghazaryan, E. V. Boldyreva, and A. M. Petrosyan. Unusual hydrogen bonding in L-cysteine hydrogen fluoride. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71(8), 733-741. https://doi.org/10.1107/s2053229615013601

    Article  CAS  Google Scholar 

  18. V. V. Ghazaryan, V. S. Minkov, E. V. Boldyreva, and A. M. Petrosyan. L-Cysteine halogenides: A new family of salts with an L-cysteine L-cysteineium dimeric cation. J. Mol. Struct., 2016, 1121, 60-69. https://doi.org/10.1016/j.molstruc.2016.05.049

    Article  CAS  Google Scholar 

  19. V. V. Ghazaryan, G. Giester, V. S. Minkov, R. A. Apreyan, E. V. Boldyreva, and A. M. Petrosyan. New members of the family of L-cysteine-based nonlinear optical crystals-(L-CysH)I, (L-CysH)I·H2O and (L-CysH⋯L-Cys)I·0.5H2O. J. Mol. Struct., 2023, 1276, 134758. https://doi.org/10.1016/j.molstruc.2022.134758

    Article  CAS  Google Scholar 

  20. V. V. Ghazaryan, T. N. Drebushchak, E. V. Boldyreva, and A. M. Petrosyan. Bis-L-cysteinium sulfate and L-cysteinium methanesulfonate. Struct. Chem., 2020, 31(5), 1919-1925. https://doi.org/10.1007/s11224-020-01610-z

    Article  CAS  Google Scholar 

  21. V. V. Ghazaryan, T. N. Drebushchak, R. A. Apreyan, E. V. Boldyreva, and A. M. Petrosyan. L-Cysteine picrates. J. Mol. Struct., 2020, 1207, 127788. https://doi.org/10.1016/j.molstruc.2020.127788

    Article  CAS  Google Scholar 

  22. Bruker. Apex4 suite. Karlsruhe, Germany: Bruker AXS, 2021.

  23. G. M. Sheldrick. A short history of SHELX. Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64(1), 112-122. https://doi.org/10.1107/s0108767307043930

    Article  Google Scholar 

  24. C. B. Hübschle, G. M. Sheldrick, and B. Dittrich. ShelXle: a Qt graphical user interface for SHELXL. J. Appl. Crystallogr., 2011, 44(6), 1281-1284. https://doi.org/10.1107/s0021889811043202

    Article  Google Scholar 

  25. S. Parsons, H. D. Flack, and T. Wagner. Use of intensity quotients and differences in absolute structure refinement. Acta Crystallogr., Sect. B: Struct. Sci. Cryst. Eng. Mater., 2013, 69(3), 249-259. https://doi.org/10.1107/s2052519213010014

    Article  CAS  Google Scholar 

  26. A. Novak. Vibrational Spectroscopy of Hydrogen Bonded Systems. In: Infrared and Raman Spectroscopy of Biological Molecules / Ed. T. M. Theophanides: NATO Advanced Study Institute Series, Vol. 43. Dordrecht, Netherlands: Kluwer, 1979, 279-303. https://doi.org/10.1007/978-94-009-9412-6_22

    Chapter  Google Scholar 

  27. K. Nakamoto. Infrared and Raman Spectra of Inorganic and Coordination Compounds. In: Handbook of Vibrational Spectroscopy / Eds. J. M. Chalmers and P.R. Griffiths. Wiley, 2006. https://doi.org/10.1002/0470027320.s4104

    Article  Google Scholar 

Download references

Funding

This work was supported in part by a research grant matsc-3822 from the Armenian National Science and Education Fund (ANSEF) based in New York, USA.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to E. V. Boldyreva or A. M. Petrosyan.

Ethics declarations

The authors declare that they have no conflicts of interests.

Additional information

Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 5, 111045.https://doi.org/10.26902/JSC_id111045

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Giester, G., Ghazaryan, V.V., Minkov, V.S. et al. L-Cysteine Nitrates. J Struct Chem 64, 917–931 (2023). https://doi.org/10.1134/S0022476623050104

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0022476623050104

Keywords

Navigation