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Synthesis And Characterization of Two New Hofmann-Type-Like Compounds From Some Alkali Metal Atoms And Glycine Anhydride

Year 2024, , 125 - 136, 04.02.2024
https://doi.org/10.18596/jotcsa.1368425

Abstract

In this study, two new compounds with their closed formula, C8H10K2N6NiO4, and C8H10Na2N6NiO4, were synthesized, the first in crystal form and the second in powder form. Various properties of these compounds were characterized by SC-XRD and FT-IR methods. Theoretical information about the compounds was obtained with the help of the Gaussian 03 program. The molecular formula that best reflects the structural properties of this first 3D compound, which is in crystalline form and has polymeric properties, can be given as {K2(GA)(H2O)2[Ni(CN)4]}n. With a similar thought, it can be suggested that the molecular formula that best reflects the structural properties of the second 3D compound in powder form and with polymeric properties will be {Na2(GA)(H2O)2[Ni(CN)4]}n. The asymmetric unit of the {K2(GA)(H2O)2[Ni(μ4-CN)4]}n compound is composed of a half Ni(II) ion, one K(I) cation, two cyanide ligands, a half GA ligand molecule, and one bounded water ligand molecule. The structure of the compound, which consists of 3D polymeric chains, is formed by various bonds between the GA molecule, K(I) cations, water ligand molecules, and Ni(CN)4 ions.

Supporting Institution

Kütahya Dumlupınar University

Project Number

2017/25

References

  • 1. Hofmann KA, Küspert F. Verbindungen von Kohlenwasserstoffen mit Metallsalzen. Z Anorg Chem. 1897 Jan;15(1):204–7. Available from: <URL>.
  • 2. Wells AF. Structural inorganic chemistry. 4th ed. Oxford: Clarendon Press; 1975. 1095 p. ISBN: 978-0-19-855354-0.
  • 3. Iwamoto T. The Hofmann-Type and Related Inclusion Compounds. In: Atwood JL, Davies JED, McNicol DD, editors. Inclusion Compounds. London: Academic Publishers; 1985. p. 29–57.
  • 4. Lewis RJ, editor. Hawley’s Condensed Chemical Dictionary [Internet]. 1st ed. Wiley; 2007 [cited 2023 Nov 17]. Available from: <URL>.
  • 5. Castellani B, Morini E, Filipponi M, Nicolini A, Palombo M, Cotana F, et al. Clathrate Hydrates for Thermal Energy Storage in Buildings: Overview of Proper Hydrate-Forming Compounds. Sustainability. 2014 Sep 30;6(10):6815–29. Available from: <URL>.
  • 6. Nohako KL, Baker PGL, Iwuoha EI. Organic Clathrate Compounds as Suitable Transducers in Electrochemical Sensing. Int J Electrochem Sci. 2015;10:6959–74. Available from: <URL>.
  • 7. Kartal Z, Şahi̇n O, Yavuz A. Synthesis, crystal structure, and characterization of two heterometallic transitionmetal citrate complexes [M=Co(II) and Cd(II)]. Turk J Chem. 2019 Apr 3;43(2):555–67. Available from: <URL>.
  • 8. Kartal Z. Synthesis, spectroscopic, thermal and structural properties of [M(3-aminopyridine)2Ni(μ-CN)2(CN)2]n (M(II)=Co and Cu) heteropolynuclear cyano-bridged complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2016 Jan;152:577–83. Available from: <URL>.
  • 9. Kartal Z, Şahin O, Yavuz A. The synthesis of two new Hofmann-type M(3-aminopyridine) 2 Ni(CN) 4 [M = Zn(II) and Cd(II)] complexes and the characterization of their crystal structure by various spectroscopic methods. Journal of Molecular Structure. 2018 Nov;1171:578–86. Available from: <URL>.
  • 10. Kartal Z, Şahi̇n O. Synthesis, spectroscopic, thermal, crystal structure properties and characterization of new Hofmann-type-like clathrates with 4-aminopyridine and water. Turk J Chem. 2021 Jun 30;45(3):616–33. Available from: <URL>.
  • 11. Bojarska J, Wolf WM. Ultra-Short Cyclo-Peptides as Bio-Inspired Therapeutics: Proline-Based 2,5-Diketopiperazines (DKP). In: The 1st International Electronic Conference on Biomolecules: Natural and Bio-Inspired Therapeutics for Human Diseases [Internet]. MDPI; 2020 [cited 2023 Nov 17]. p. 10. Available from: <URL>.
  • 12. Sarangarajan TR, Panchanatheswaran K, Low JN, Glidewell C. Piperazine-2,5-dione–oxalic acid–water (1/1/2) and a redetermination of piperazine-2,5-dione, both at 120 K: hydrogen-bonded sheets containing multiple ring types. Acta Crystallogr C Cryst Struct Commun. 2005 Feb 15;61(2):o118–21. Available from: <URL>.
  • 13. Sheldrick GM. A short history of SHELX. Acta Crystallogr A Found Crystallogr. 2008 Jan 1;64(1):112–22. Available from: <URL>.
  • 14. Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem. 2015 Jan 1;71(1):3–8. Available from: <URL>.
  • 15. Bruker. APEX2. Bruker AXS Inc.; 2004.
  • 16. Macrae CF, Sovago I, Cottrell SJ, Galek PTA, McCabe P, Pidcock E, et al. Mercury 4.0 : from visualization to analysis, design and prediction. J Appl Crystallogr. 2020 Feb 1;53(1):226–35. Available from: <URL>.
  • 17. Farrugia LJ. WinGX and ORTEP for Windows : an update. J Appl Crystallogr. 2012 Aug 1;45(4):849–54. Available from: <URL>.
  • 18. Kartal Z, Şahin O, Yavuz A. The synthesis of two new Hofmann-type M(3-aminopyridine) 2 Ni(CN) 4 [M = Zn(II) and Cd(II)] complexes and the characterization of their crystal structure by various spectroscopic methods. Journal of Molecular Structure. 2018 Nov;1171:578–86. Available from: <URL>.
  • 19. Kobrsi I, Zheng W, Knox JE, Heeg MJ, Schlegel HB, Winter CH. Experimental and Theoretical Study of the Coordination of 1,2,4-Triazolato, Tetrazolato, and Pentazolato Ligands to the [K(18-crown-6)] + Fragment. Inorg Chem. 2006 Oct 1;45(21):8700–10. Available from: <URL>.
  • 20. Saritemur G, Nomen Miralles L, Husson D, Pitak MB, Coles SJ, Wallis JD. Two modes of peri -interaction between an aldehyde group and a carboxylate anion in naphthalaldehydate salts. CrystEngComm. 2016;18(6):948–61. Available from: <URL>.
  • 21. Kartal Z, Şahi̇N O, Yavuz A. Synthesis of Hofmann-type Zn(H2O)2Ni(CN)4.nG (G = water and 1,4-dioxane)clathrates and the determination of their structural properties by variousspectroscopic methods. Turk J Chem. 2019 Dec 9;43(6):1608–21. Available from: <URL>.
  • 22. Mendham AP, Dines TJ, Snowden MJ, Withnall R, Chowdhry BZ. IR/Raman spectroscopy and DFT calculations of cyclic di‐amino acid peptides. Part III: comparison of solid state and solution structures of cyclo( L ‐Ser‐ L ‐Ser). J Raman Spectroscopy. 2009 Nov;40(11):1508–20. Available from: <URL>.
  • 23. Kartha G, Varughese KI, Lu CT. Structure of the 1:2 complex of 2,5-piperazinedione and formic acid. Acta Crystallogr B Struct Sci. 1981 Sep 1;37(9):1798–800. Available from: <URL>.
  • 24. Wang L, Zhao L, Liu W, Chen R, Gu Y, Yang Y. Co-crystallization of glycine anhydride with the hydroxybenzoic acids: Controlled formation of dimers via synthons cooperation and structural characterization. Sci China Chem. 2012 Nov;55(11):2381–7. Available from: <URL>.
  • 25. Nataraj A, Balachandran V, Karthick T. Molecular orbital studies (hardness, chemical potential, electrophilicity, and first electron excitation), vibrational investigation and theoretical NBO analysis of 2-hydroxy-5-bromobenzaldehyde by density functional method. Journal of Molecular Structure. 2013 Jan;1031:221–33. Available from: <URL>.
  • 26. Tkatchenko A, Alfè D, Kim KS. First-Principles Modeling of Non-Covalent Interactions in Supramolecular Systems: The Role of Many-Body Effects. J Chem Theory Comput. 2012 Nov 13;8(11):4317–22. Available from: <URL>.
  • 27. Nakamoto K. Infrared and Raman spectra of inorganic and coordination compounds. B: Applications in coordination, organometallic, and bioinorganic chemistry. 6. ed. Hoboken, NJ: Wiley; 2009. 408 p. ISBN: 978-0-471-74493-1.
  • 28. Carmona P, Molina M, Escobar R. Studies on aminopyridines in aqueous solution by laser Raman spectroscopy. Spectrochimica Acta Part A: Molecular Spectroscopy. 1993 Jan;49(1):1–9. Available from: <URL>.
  • 29. Khoma RE, Gelmboldt VO, Baumer VN, Shishkin OV, Koroeva LV. Synthesis and structure of aminoguanidinium sulfite monohydrate. Russ J Inorg Chem. 2013 Jul;58(7):843–7. Available from: <URL>.
  • 30. Ma S, Wang M, Liu Y, Yang C, Chi L, Li Q. Ab initio study of spectroscopic properties and anharmonic force fields of MNH2 (M = Li, Na, K). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2021 May;253:119591. Available from: <URL>.
  • 31. Sharpe AG. The chemistry of cyano complexes of the transition metals. London: Acad. Pr; 1976. 11 p. (Organometallic chemistry). ISBN: 978-0-12-638450-5.
  • 32. McCullough RL, Jones LH, Crosby GA. An analysis of the vibrational spectrum of the tetracyanonickelate(II) ion in a crystal lattice. Spectrochimica Acta. 1960 Jan;16(8):929–44. Available from: <URL>.
  • 33. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 03, Revision D. 01. Gaussian, Inc.; 2004.
  • 34. Dennington R, Keith T, Millam J. Gauss View, Version 4.1.2. Semichem Inc; 2007.
Year 2024, , 125 - 136, 04.02.2024
https://doi.org/10.18596/jotcsa.1368425

Abstract

Project Number

2017/25

References

  • 1. Hofmann KA, Küspert F. Verbindungen von Kohlenwasserstoffen mit Metallsalzen. Z Anorg Chem. 1897 Jan;15(1):204–7. Available from: <URL>.
  • 2. Wells AF. Structural inorganic chemistry. 4th ed. Oxford: Clarendon Press; 1975. 1095 p. ISBN: 978-0-19-855354-0.
  • 3. Iwamoto T. The Hofmann-Type and Related Inclusion Compounds. In: Atwood JL, Davies JED, McNicol DD, editors. Inclusion Compounds. London: Academic Publishers; 1985. p. 29–57.
  • 4. Lewis RJ, editor. Hawley’s Condensed Chemical Dictionary [Internet]. 1st ed. Wiley; 2007 [cited 2023 Nov 17]. Available from: <URL>.
  • 5. Castellani B, Morini E, Filipponi M, Nicolini A, Palombo M, Cotana F, et al. Clathrate Hydrates for Thermal Energy Storage in Buildings: Overview of Proper Hydrate-Forming Compounds. Sustainability. 2014 Sep 30;6(10):6815–29. Available from: <URL>.
  • 6. Nohako KL, Baker PGL, Iwuoha EI. Organic Clathrate Compounds as Suitable Transducers in Electrochemical Sensing. Int J Electrochem Sci. 2015;10:6959–74. Available from: <URL>.
  • 7. Kartal Z, Şahi̇n O, Yavuz A. Synthesis, crystal structure, and characterization of two heterometallic transitionmetal citrate complexes [M=Co(II) and Cd(II)]. Turk J Chem. 2019 Apr 3;43(2):555–67. Available from: <URL>.
  • 8. Kartal Z. Synthesis, spectroscopic, thermal and structural properties of [M(3-aminopyridine)2Ni(μ-CN)2(CN)2]n (M(II)=Co and Cu) heteropolynuclear cyano-bridged complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2016 Jan;152:577–83. Available from: <URL>.
  • 9. Kartal Z, Şahin O, Yavuz A. The synthesis of two new Hofmann-type M(3-aminopyridine) 2 Ni(CN) 4 [M = Zn(II) and Cd(II)] complexes and the characterization of their crystal structure by various spectroscopic methods. Journal of Molecular Structure. 2018 Nov;1171:578–86. Available from: <URL>.
  • 10. Kartal Z, Şahi̇n O. Synthesis, spectroscopic, thermal, crystal structure properties and characterization of new Hofmann-type-like clathrates with 4-aminopyridine and water. Turk J Chem. 2021 Jun 30;45(3):616–33. Available from: <URL>.
  • 11. Bojarska J, Wolf WM. Ultra-Short Cyclo-Peptides as Bio-Inspired Therapeutics: Proline-Based 2,5-Diketopiperazines (DKP). In: The 1st International Electronic Conference on Biomolecules: Natural and Bio-Inspired Therapeutics for Human Diseases [Internet]. MDPI; 2020 [cited 2023 Nov 17]. p. 10. Available from: <URL>.
  • 12. Sarangarajan TR, Panchanatheswaran K, Low JN, Glidewell C. Piperazine-2,5-dione–oxalic acid–water (1/1/2) and a redetermination of piperazine-2,5-dione, both at 120 K: hydrogen-bonded sheets containing multiple ring types. Acta Crystallogr C Cryst Struct Commun. 2005 Feb 15;61(2):o118–21. Available from: <URL>.
  • 13. Sheldrick GM. A short history of SHELX. Acta Crystallogr A Found Crystallogr. 2008 Jan 1;64(1):112–22. Available from: <URL>.
  • 14. Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem. 2015 Jan 1;71(1):3–8. Available from: <URL>.
  • 15. Bruker. APEX2. Bruker AXS Inc.; 2004.
  • 16. Macrae CF, Sovago I, Cottrell SJ, Galek PTA, McCabe P, Pidcock E, et al. Mercury 4.0 : from visualization to analysis, design and prediction. J Appl Crystallogr. 2020 Feb 1;53(1):226–35. Available from: <URL>.
  • 17. Farrugia LJ. WinGX and ORTEP for Windows : an update. J Appl Crystallogr. 2012 Aug 1;45(4):849–54. Available from: <URL>.
  • 18. Kartal Z, Şahin O, Yavuz A. The synthesis of two new Hofmann-type M(3-aminopyridine) 2 Ni(CN) 4 [M = Zn(II) and Cd(II)] complexes and the characterization of their crystal structure by various spectroscopic methods. Journal of Molecular Structure. 2018 Nov;1171:578–86. Available from: <URL>.
  • 19. Kobrsi I, Zheng W, Knox JE, Heeg MJ, Schlegel HB, Winter CH. Experimental and Theoretical Study of the Coordination of 1,2,4-Triazolato, Tetrazolato, and Pentazolato Ligands to the [K(18-crown-6)] + Fragment. Inorg Chem. 2006 Oct 1;45(21):8700–10. Available from: <URL>.
  • 20. Saritemur G, Nomen Miralles L, Husson D, Pitak MB, Coles SJ, Wallis JD. Two modes of peri -interaction between an aldehyde group and a carboxylate anion in naphthalaldehydate salts. CrystEngComm. 2016;18(6):948–61. Available from: <URL>.
  • 21. Kartal Z, Şahi̇N O, Yavuz A. Synthesis of Hofmann-type Zn(H2O)2Ni(CN)4.nG (G = water and 1,4-dioxane)clathrates and the determination of their structural properties by variousspectroscopic methods. Turk J Chem. 2019 Dec 9;43(6):1608–21. Available from: <URL>.
  • 22. Mendham AP, Dines TJ, Snowden MJ, Withnall R, Chowdhry BZ. IR/Raman spectroscopy and DFT calculations of cyclic di‐amino acid peptides. Part III: comparison of solid state and solution structures of cyclo( L ‐Ser‐ L ‐Ser). J Raman Spectroscopy. 2009 Nov;40(11):1508–20. Available from: <URL>.
  • 23. Kartha G, Varughese KI, Lu CT. Structure of the 1:2 complex of 2,5-piperazinedione and formic acid. Acta Crystallogr B Struct Sci. 1981 Sep 1;37(9):1798–800. Available from: <URL>.
  • 24. Wang L, Zhao L, Liu W, Chen R, Gu Y, Yang Y. Co-crystallization of glycine anhydride with the hydroxybenzoic acids: Controlled formation of dimers via synthons cooperation and structural characterization. Sci China Chem. 2012 Nov;55(11):2381–7. Available from: <URL>.
  • 25. Nataraj A, Balachandran V, Karthick T. Molecular orbital studies (hardness, chemical potential, electrophilicity, and first electron excitation), vibrational investigation and theoretical NBO analysis of 2-hydroxy-5-bromobenzaldehyde by density functional method. Journal of Molecular Structure. 2013 Jan;1031:221–33. Available from: <URL>.
  • 26. Tkatchenko A, Alfè D, Kim KS. First-Principles Modeling of Non-Covalent Interactions in Supramolecular Systems: The Role of Many-Body Effects. J Chem Theory Comput. 2012 Nov 13;8(11):4317–22. Available from: <URL>.
  • 27. Nakamoto K. Infrared and Raman spectra of inorganic and coordination compounds. B: Applications in coordination, organometallic, and bioinorganic chemistry. 6. ed. Hoboken, NJ: Wiley; 2009. 408 p. ISBN: 978-0-471-74493-1.
  • 28. Carmona P, Molina M, Escobar R. Studies on aminopyridines in aqueous solution by laser Raman spectroscopy. Spectrochimica Acta Part A: Molecular Spectroscopy. 1993 Jan;49(1):1–9. Available from: <URL>.
  • 29. Khoma RE, Gelmboldt VO, Baumer VN, Shishkin OV, Koroeva LV. Synthesis and structure of aminoguanidinium sulfite monohydrate. Russ J Inorg Chem. 2013 Jul;58(7):843–7. Available from: <URL>.
  • 30. Ma S, Wang M, Liu Y, Yang C, Chi L, Li Q. Ab initio study of spectroscopic properties and anharmonic force fields of MNH2 (M = Li, Na, K). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2021 May;253:119591. Available from: <URL>.
  • 31. Sharpe AG. The chemistry of cyano complexes of the transition metals. London: Acad. Pr; 1976. 11 p. (Organometallic chemistry). ISBN: 978-0-12-638450-5.
  • 32. McCullough RL, Jones LH, Crosby GA. An analysis of the vibrational spectrum of the tetracyanonickelate(II) ion in a crystal lattice. Spectrochimica Acta. 1960 Jan;16(8):929–44. Available from: <URL>.
  • 33. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 03, Revision D. 01. Gaussian, Inc.; 2004.
  • 34. Dennington R, Keith T, Millam J. Gauss View, Version 4.1.2. Semichem Inc; 2007.
There are 34 citations in total.

Details

Primary Language English
Subjects Crystallography
Journal Section RESEARCH ARTICLES
Authors

Zeki Kartal 0000-0001-9739-0858

Zarife Sibel Şahin 0000-0003-2745-7871

Project Number 2017/25
Publication Date February 4, 2024
Submission Date October 2, 2023
Acceptance Date November 3, 2023
Published in Issue Year 2024

Cite

Vancouver Kartal Z, Şahin ZS. Synthesis And Characterization of Two New Hofmann-Type-Like Compounds From Some Alkali Metal Atoms And Glycine Anhydride. JOTCSA. 2024;11(1):125-36.