Preparation, identification and investigation of the crystal structure of bivalent copper complex with new ligand 3,3ʹ,3ʺ,3ʺʹ-(propane-1,2-diylbis(azanetriyl))tetrapropanoic acid

Document Type : Original Article

Authors

Inorganic Chemistry, Faculty of Chemistry, Payam Noor University, Tehran, Iran

Abstract

In this research, a new compound of tetramethyl-3,3ʹ,3ʺ,3ʺʹ-(propane-1,2-diylbis(azanetriyl))tetrapropionate (TPAT) was prepared from the reaction of propane-1,2-diamine and methyl acrylate in methanol solvent. The composition of TPAT in the base environment, simultaneously with the formation of the complex, was reaction to the ligand 3,3ʹ,3ʺ,3ʺʹ-(propane-1,2-diylbis(azanetriyl))tetrapropanoic acid (H4PAT). 3,3ʹ,3ʺ,3ʺʹ-(propane-1,2-diylbis(azanetriyl))tetrapropionate copper(II) complex [Cu(H2PAT)] was identified by FT-IR, 1H NMR spectroscopy, elemental analysis (CHN) and its structure was determined by X-ray single crystal. H4PAT ligand is coordinated to copper atom through two nitrogen atoms, two oxygen atoms from propionate ion and one carbonyl group from propanoic acid and has a distorted square pyramidal geometry. This complex is crystallized in orthorhombic crystal system with space group Pna21 and Z=4 with a=14.1429(8) Å, b=14.1429(8) Å and c=9.9781(3) Å. The catalytic application of this complex was investigated. 2 mmol of [Cu(H2PAT)] complex was used for the coupling of phenyl bromide, under reflux conditions, without solvent in 120 minutes, and the biphenyl product was formed with 80% efficiency.

Keywords

References

  1. [1] Bipin B.M., Debendra P., "Polymetallic complexes: Part V. ONNO tetradentate N,N′-bis(acetoacetanilide)-1, 3-diaminopropane complexes of cobalt(II), copper(II) and zinc(II)", Transition Met. Chemistry 9 (1984) 117. [DOI:10.1007/BF00618589]
  2. [1] Bipin B.M., Debendra P., "Polymetallic complexes: Part V. ONNO tetradentate N,N′-bis(acetoacetanilide)-1, 3-diaminopropane complexes of cobalt(II), copper(II) and zinc(II)", Transition Met. Chemistry 9 (1984) 117. [DOI:10.1007/BF00618589]
  3. [2] Corey EJ., Sarshar S., Azimioara MD., Newbold RC., Noe MC., "X-ray Crystal and NMR Structure of a Highly Reactive Bidentate 1,2-Diamine−OsO4 Complex, Formally a 20-Electron Outer Valence Shell Species. Mechanistic Implications for the 1,2-Diamine-Accelerated Dihydroxylation of Olefins by OsO4", J. Am. Chem. Soc. 118 (1996) 7851. [DOI:10.1021/ja960536d]
  4. [2] Corey EJ., Sarshar S., Azimioara MD., Newbold RC., Noe MC., "X-ray Crystal and NMR Structure of a Highly Reactive Bidentate 1,2-Diamine−OsO4 Complex, Formally a 20-Electron Outer Valence Shell Species. Mechanistic Implications for the 1,2-Diamine-Accelerated Dihydroxylation of Olefins by OsO4", J. Am. Chem. Soc. 118 (1996) 7851. [DOI:10.1021/ja960536d]
  5. [3] Zhenrong Q., Tan TC., "BOD measurement in the presence of heavy metal ions using a thermally-killed-Bacillus subtilis biosensor", Water Res 33 (1999) 2923. [DOI:10.1016/S0043-1354(99)00011-1]
  6. [3] Zhenrong Q., Tan TC., "BOD measurement in the presence of heavy metal ions using a thermally-killed-Bacillus subtilis biosensor", Water Res 33 (1999) 2923. [DOI:10.1016/S0043-1354(99)00011-1]
  7. [4] Bonnaud L., Pascault JP., Sautereau H., "Kinetic of a thermoplastic-modified epoxy-aromatic diamine formulation: modeling and influence of a trifunctional epoxy prepolymer", Eur. Polymer J. 36 (2000) 1313-1321. [DOI:10.1016/S0014-3057(99)00197-4]
  8. [4] Bonnaud L., Pascault JP., Sautereau H., "Kinetic of a thermoplastic-modified epoxy-aromatic diamine formulation: modeling and influence of a trifunctional epoxy prepolymer", Eur. Polymer J. 36 (2000) 1313-1321. [DOI:10.1016/S0014-3057(99)00197-4]
  9. [5] Ali SA., Saeed MT., "Synthesis and corrosion inhibition study of some 1,6-hexanediamine-based N,N-diallyl quaternary ammonium salts and their polymers", Polymer 42 (2001) 2785-2794. [DOI:10.1016/S0032-3861(00)00665-0]
  10. [5] Ali SA., Saeed MT., "Synthesis and corrosion inhibition study of some 1,6-hexanediamine-based N,N-diallyl quaternary ammonium salts and their polymers", Polymer 42 (2001) 2785-2794. [DOI:10.1016/S0032-3861(00)00665-0]
  11. [6] Wang L., Tsai S., "Simultaneous determination of oxidative hair dye p-phenylenediamine and its metabolites in human rabbit biological fl uids", Analyt. Biochemistry. 312 (2003) 201. [DOI:10.1016/S0003-2697(02)00501-8]
  12. [6] Wang L., Tsai S., "Simultaneous determination of oxidative hair dye p-phenylenediamine and its metabolites in human rabbit biological fl uids", Analyt. Biochemistry. 312 (2003) 201. [DOI:10.1016/S0003-2697(02)00501-8]
  13. [7] Durmuş S., Cand. Sci. (Chem.) Dissertation. Ankara. (1992).
  14. [7] Durmuş S., Cand. Sci. (Chem.) Dissertation. Ankara. (1992).
  15. [8] Turan N., Colak N., Sekerci M., "Synthesis and Characterization of Cu(II), Ni(II) and Cd(II) Complexes With 3,5-Diamino-4-(4-Bromo-Phenylazo)-1H-Pyrazole", International Journal of Natural and Engineering Sciences 2 (3) (2008) 27-32.
  16. [8] Turan N., Colak N., Sekerci M., "Synthesis and Characterization of Cu(II), Ni(II) and Cd(II) Complexes With 3,5-Diamino-4-(4-Bromo-Phenylazo)-1H-Pyrazole", International Journal of Natural and Engineering Sciences 2 (3) (2008) 27-32.
  17. [9] Garnovskii AD., Kharisov BI., "Aryl and 1,3-dioxoindanyl derivatives of azoles and azines", Synthetic Coordination and Org. Met. Chemistry. New York-Basel (2003).
  18. [9] Garnovskii AD., Kharisov BI., "Aryl and 1,3-dioxoindanyl derivatives of azoles and azines", Synthetic Coordination and Org. Met. Chemistry. New York-Basel (2003).
  19. [10] Öztürk ÖF., Şekerci M., Özdemir E., "Preparation of complexes of 1-amino-6,7-o-cyclohexylidene-4-azaheptane with transition metal acetates", Russian Journal of General Chemistry. 76 (1) (2006) 33-36. [DOI:10.1134/S1070363206010075]
  20. [10] Öztürk ÖF., Şekerci M., Özdemir E., "Preparation of complexes of 1-amino-6,7-o-cyclohexylidene-4-azaheptane with transition metal acetates", Russian Journal of General Chemistry. 76 (1) (2006) 33-36. [DOI:10.1134/S1070363206010075]
  21. [11] J. Radanovic D., Ianelli S., Pelosi G., D. Matovic Z., Tasic-Stojanovic S., E. Douglas B., "Some hexadentate Ni (II)-edta-type complexes containing five-membered diamine rings. The molecular and crystal structure of the trans(O5) isomer of barium(ethylenediamine-N,N'-diacetato-N,N'-di-3-propionato) nickelate(II) hexahydrate, trans(O5)-Ba[Ni(eddadp)].6H2O, and strain analysis of edta-type chelates in relation to their octahedral distortion", Inorganica Chimica Acta. 278 (1998) 66-75. [DOI:10.1016/S0020-1693(98)00009-7]
  22. [11] J. Radanovic D., Ianelli S., Pelosi G., D. Matovic Z., Tasic-Stojanovic S., E. Douglas B., "Some hexadentate Ni (II)-edta-type complexes containing five-membered diamine rings. The molecular and crystal structure of the trans(O5) isomer of barium(ethylenediamine-N,N'-diacetato-N,N'-di-3-propionato) nickelate(II) hexahydrate, trans(O5)-Ba[Ni(eddadp)].6H2O, and strain analysis of edta-type chelates in relation to their octahedral distortion", Inorganica Chimica Acta. 278 (1998) 66-75. [DOI:10.1016/S0020-1693(98)00009-7]
  23. [12] Mingjun H., Jianyong H., Xin W., Sai L., Chenyang Z., Hongliang Z., Wei S., Tong Y. "Deep purification of copper from Cu(II)-EDTA acidic wastewater by Fe(III) replacement/diethyldithiocarbamate precipitation", Chemosphere..300 (2022) 134546. [DOI:10.1016/j.chemosphere.2022.134546]
  24. [12] Mingjun H., Jianyong H., Xin W., Sai L., Chenyang Z., Hongliang Z., Wei S., Tong Y. "Deep purification of copper from Cu(II)-EDTA acidic wastewater by Fe(III) replacement/diethyldithiocarbamate precipitation", Chemosphere..300 (2022) 134546. [DOI:10.1016/j.chemosphere.2022.134546]
  25. [13] Siew Siang L., Hongwei B., Zhaoyang L., Darren Delai S., "Green Approach for Photocatalytic Cu(II)-EDTA Degradation over TiO2: Toward Environmental Sustainability", Environ. Sci. Technol. 49(4) (2015) 2541-2548. [DOI:10.1021/es504711e]
  26. [13] Siew Siang L., Hongwei B., Zhaoyang L., Darren Delai S., "Green Approach for Photocatalytic Cu(II)-EDTA Degradation over TiO2: Toward Environmental Sustainability", Environ. Sci. Technol. 49(4) (2015) 2541-2548. [DOI:10.1021/es504711e]
  27. [14] Hakimi M., Kukovec B.-M., Minoura M., "2D s-d Mixed-Metal Coordination Polymer Containing Potassium, Chromium(III) and Dipicolinate Ions: Preparation and Crystal Structure", J. Chem. Crystallogr. 42 (2012) 290-294. [DOI:10.1007/s10870-011-0242-0]
  28. [14] Hakimi M., Kukovec B.-M., Minoura M., "2D s-d Mixed-Metal Coordination Polymer Containing Potassium, Chromium(III) and Dipicolinate Ions: Preparation and Crystal Structure", J. Chem. Crystallogr. 42 (2012) 290-294. [DOI:10.1007/s10870-011-0242-0]
  29. [15] Kim T., Kim S., Lee D-g., Lim C-S., Seo B., "Preparation of a branched amine and physical and thermal studies of epoxy compositions including the amine compound", J. APPL. POLYM. SCI (2018) 1-7. [DOI:10.1002/app.46233]
  30. [15] Kim T., Kim S., Lee D-g., Lim C-S., Seo B., "Preparation of a branched amine and physical and thermal studies of epoxy compositions including the amine compound", J. APPL. POLYM. SCI (2018) 1-7. [DOI:10.1002/app.46233]
  31. [16] Afzaal M., Flynn E., Malik M. A., O̓Brien P., Motevalli M., Mixed ligand chelates of copper(II) with substituted diamines", Polyhedron 24 (2005) 1101-1107. [DOI:10.1016/j.poly.2005.04.002]
  32. [16] Afzaal M., Flynn E., Malik M. A., O̓Brien P., Motevalli M., Mixed ligand chelates of copper(II) with substituted diamines", Polyhedron 24 (2005) 1101-1107. [DOI:10.1016/j.poly.2005.04.002]
  33. [17] Hakimi M., Kukovec B.-M., Schuh E., Normohammadzadeh, Z., Mohr F., "Preparation and Crystal Structure of Lead (II) Complex with Propane-1,2-Diamine', J. Chem. Crystallogr. 42 (2012) 180-185. [DOI:10.1007/s10870-011-0221-5]
  34. [17] Hakimi M., Kukovec B.-M., Schuh E., Normohammadzadeh, Z., Mohr F., "Preparation and Crystal Structure of Lead (II) Complex with Propane-1,2-Diamine', J. Chem. Crystallogr. 42 (2012) 180-185. [DOI:10.1007/s10870-011-0221-5]
  35. [18] Abolghasempour S.A., Salimi A., Nakhaeipour A., "Synthesis, characterization and crystal structure determination of new coordination polymer of zinc(II) containing N-(4-pyridyl)isonocotinamide ligand (in Persian)", Iranian Journal of Crystallography and Mineralogy (IJCM) 28(4) (2020) 1023-1036. [DOI:10.52547/ijcm.28.4.1023]
  36. [18] Abolghasempour S.A., Salimi A., Nakhaeipour A., "Synthesis, characterization and crystal structure determination of new coordination polymer of zinc(II) containing N-(4-pyridyl)isonocotinamide ligand (in Persian)", Iranian Journal of Crystallography and Mineralogy (IJCM) 28(4) (2020) 1023-1036. [DOI:10.52547/ijcm.28.4.1023]
  37. [19] Addison A., Rao T., Reedjik J., Van Rijn J., Verschoor G., 'Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane] copper(II) perchlorate", J. Chem. Soc., Dalton Trans. (1984) 1349-1356. [DOI:10.1039/DT9840001349]
  38. [19] Addison A., Rao T., Reedjik J., Van Rijn J., Verschoor G., 'Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane] copper(II) perchlorate", J. Chem. Soc., Dalton Trans. (1984) 1349-1356. [DOI:10.1039/DT9840001349]
  39. [20] Takjoo R., Hakimi M., Seyyedin M., Abrishami M., "New 2-pyridinealdehyde N4 -hydroxyethyl thiosemicarbazone and their Cd(II) and Cu(II) complexes: synthesis, spectral, in vitro antibacterial activity and molecular and supramolecular structure study', J. Sulfur Chem. 31 (2010) 415-426. [DOI:10.1080/17415993.2010.507815]
  40. [20] Takjoo R., Hakimi M., Seyyedin M., Abrishami M., "New 2-pyridinealdehyde N4 -hydroxyethyl thiosemicarbazone and their Cd(II) and Cu(II) complexes: synthesis, spectral, in vitro antibacterial activity and molecular and supramolecular structure study', J. Sulfur Chem. 31 (2010) 415-426. [DOI:10.1080/17415993.2010.507815]
  41. [21] Hakimi M., Mardani Z., Moeini K., Mohr F., Schuh E., Vahedi H., Synthesis, "Crystallographic and Spectral Characterization of a Cadmium Chloride Complex Containing Novel Imidazo[1,5-a]Pyridine Derivative", Z. Naturforsch. 67b (2012) 452-458. [DOI:10.5560/znb.2012-0064]
  42. [21] Hakimi M., Mardani Z., Moeini K., Mohr F., Schuh E., Vahedi H., Synthesis, "Crystallographic and Spectral Characterization of a Cadmium Chloride Complex Containing Novel Imidazo[1,5-a]Pyridine Derivative", Z. Naturforsch. 67b (2012) 452-458. [DOI:10.5560/znb.2012-0064]
  43. [22] Ahmadi Sh., Delir Kheirollahi Nezhad P., "Synthesis, identification and determination of the crystal structure of a new copper (II) complex based on schiff's tetradentate ligand of pyridine and 1,6-diamino-3-azaxane (in Persian)", Iranian Journal of Crystallography and Mineralogy (IJCM) 29(3) (2021) 707-716. [DOI:10.52547/ijcm.29.3.707]
  44. [22] Ahmadi Sh., Delir Kheirollahi Nezhad P., "Synthesis, identification and determination of the crystal structure of a new copper (II) complex based on schiff's tetradentate ligand of pyridine and 1,6-diamino-3-azaxane (in Persian)", Iranian Journal of Crystallography and Mineralogy (IJCM) 29(3) (2021) 707-716. [DOI:10.52547/ijcm.29.3.707]
  45. [23] Hekmati M., Yousefi M., Ziyadi H., Ghasemi E., Safari Mehr P., Veisi H., Maleki B., "catalytic applications of coated nanopalladium particles coated on modified GO by Thymbraspicata extract in Suzuki coupling reactions (in Persian)", J. Appl. Chem. 16(58) (1400) 233-244.
  46. [23] Hekmati M., Yousefi M., Ziyadi H., Ghasemi E., Safari Mehr P., Veisi H., Maleki B., "catalytic applications of coated nanopalladium particles coated on modified GO by Thymbraspicata extract in Suzuki coupling reactions (in Persian)", J. Appl. Chem. 16(58) (1400) 233-244.
  47. [24] Hassani H., Jahani Z., "Preparation, characterization and application of magnetic Fe3O4@CeO2 nanocatalysts for the synthesis of diindolyloxindole derivatives (in Persian)", J. Appl. Chem. 16(58) (1400) 149-166.
  48. [24] Hassani H., Jahani Z., "Preparation, characterization and application of magnetic Fe3O4@CeO2 nanocatalysts for the synthesis of diindolyloxindole derivatives (in Persian)", J. Appl. Chem. 16(58) (1400) 149-166.
Iranian Journal of Crystallography and Mineralogy
Volume 31, Issue 3 - Serial Number 91
October 2023
Pages 575-582

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  • Receive Date: 20 February 2023
  • Revise Date: 15 March 2023
  • Accept Date: 05 April 2023

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