DOI QR코드

DOI QR Code

1D-Coordination Polymer Formed by Structural Conversion of an Oxazolidine Ligand in Reaction with the Copper(II) Halides

  • Mardani, Zahra (Inorganic Chemistry Department, Faculty of Chemistry, Urmia University) ;
  • Golsanamlou, Vali (Inorganic Chemistry Department, Faculty of Chemistry, Urmia University) ;
  • Jabbarzadeh, Zahra (Inorganic Chemistry Department, Faculty of Chemistry, Urmia University) ;
  • Moeini, Keyvan (Chemistry Department, Payame Noor University,) ;
  • Carpenter-Warren, Cameron (EaStCHEM School of Chemistry, University of St Andrews) ;
  • Slawin, Alexandra M.Z. (EaStCHEM School of Chemistry, University of St Andrews) ;
  • Woollins, J. Derek (EaStCHEM School of Chemistry, University of St Andrews)
  • Received : 2018.05.20
  • Accepted : 2018.07.12
  • Published : 2018.10.20

Abstract

A 1D-coordination polymer of $1D-\{Cu({\mu}-picolinato)_2\}$ $\{Hakimi,\;2012\;\sharp73\}_n$ (1), was prepared by the reactions between 2-(2-(pyridin-2-yl)oxazolidin-3-yl)ethanol (AEPC) ligand and $CuCl_2$ or $CuBr_2$. The product was characterized by elemental analysis, UV-Vis, FT-IR spectroscopy and single-crystal X-ray diffraction. The X-ray analysis results revealed that the AEPC ligand, after reactions with the copper(II) chloride or bromide, gives the same product - $1D-\{Cu({\mu}-picolinato)_2\}_n$ (1). The coordination modes for various picolinate-based ligands were extracted from the Cambridge Structural Database (CSD). In the crystal structure of 1, the copper atom has a $CuN_2O_4$ environment and octahedral geometry, which is distorted by elongation of the axial bond lengths due to the Jahn-Teller effect.

Keywords

References

  1. Sayama, S. Oxidative Syntheses and Ring Opening of Oxazolines and Related Compounds by Ammonium Tribromide. Heterocycles 2017, 94, 1997. https://doi.org/10.3987/REV-17-866
  2. Piancatelli, G.; D'Auria, M.; D'Onofrio, F. Synthesis of 1,4-Dicarbonyl Compounds and Cyclopentenones from Furans. Synthesis 1994, 1994, 867. https://doi.org/10.1055/s-1994-25591
  3. Bensa, D.; Coldham, I.; Feinaugle, P.; Pathak, R. B.; Butlin, R. J. Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents. Org. Biomol. Chem. 2008, 6, 1410. https://doi.org/10.1039/b800849c
  4. Haidukewych, D.; Meyers, A. I. A mild conversion of carboxylic acids to 2-oxazolines and their utility as a carboxyl masking group against lithium aluminum hydride. Tetrahedron Lett. 1972, 13, 3031. https://doi.org/10.1016/S0040-4039(01)85001-2
  5. Moloney, G. P.; Iskander, M. N.; Craik, D. J. Stability Studies of Oxazolidine-Based Compounds Using 1H NMR Spectroscopy. J. Pharm. Sci. 2010, 99, 3362. https://doi.org/10.1002/jps.22108
  6. Mardani, Z.; Golsanamlou, V.; Khodavandegar, S.; Moeini, K.; Slawin, A. M. Z.; Woollins, J. D. The coordination of a multidentate NxOy-donor (x and $y{\leq}2$) oxazolidine-based ligand with Cd(II) and Hg(II); Structural, spectral, and theoretical studies. J. Coord. Chem. 2018, 71, 1. https://doi.org/10.1080/00958972.2018.1434517
  7. In CrystalClear-SM Expert, v3.1b27. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan, 2013.
  8. CrysAlisPro v1.171.38.41. Rigaku Oxford Diffraction, Rigaku Corporation, Oxford, U.K. 2015.
  9. Sheldrick, G. SHELXT - Integrated space-group and crystalstructure determination. Acta Crystallogr. 2015, A71, 3.
  10. Sheldrick, G. Acta Crystallogr. 2015, C71, 3.
  11. CrystalStructure v4.2. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. 2015.
  12. (a) Farrugia, L. J. ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Crystallogr. 1997, 30, 565.
  13. (b) Burnett, M. N.; Johnson, C. K. Ortep-III, Report ORNL-6895. Oak Ridge National Laboratory: Oak Ridge, Tennessee, U.S., 1996.
  14. Bergerhof, G.; Berndt, M.; Brandenburg, K. Evaluation of Crystallographic Data with the Program DIAMOND. J. Res. Natl. Inst. Stand. Technol. 1996, 101, 221. https://doi.org/10.6028/jres.101.023
  15. Zurowska, B.; Mrozinski, J.; Slepokura, K. Polyhedron 2007, 26, 3379. https://doi.org/10.1016/j.poly.2007.03.024
  16. (a) Nakamoto, K. In Infrared and Raman Spectra of Inorganic and Coordination Compouns, 6th, Ed.; John Wiley, Hoboken: 2009; pp. 232, 283, 285.
  17. (b) Hakimi, M.; Moeini, K.; Mardani, Z.; Khorrami, F. Crystal Structure and Characterization of a New Eight Coordinated Cadmium Complex J. Korean Chem. Soc. 2013, 57, 352. https://doi.org/10.5012/jkcs.2013.57.3.352
  18. (a) Hosseini, S. G.; Moeini, K.; Abdelbaky, M. S. M.; Garcia-Granda, S. A coordination polymer of mercury(II) formed by triazole-based and chloride linkers. Z. Naturforsch 2017; Vol. 72b, p 573.
  19. (b) Marandi, F.; Moeini, K.; Ghasemzadeh, S.; Mardani, Z.; Quah, C. K.; Loh, W.-S. Synthesis, spectral and X-ray diffraction of two new 2D lead(II) coordination polymers formed by nicotinic acid Noxide linkers. J. Mol. Struct. 2017, 1149, 92. https://doi.org/10.1016/j.molstruc.2017.06.039
  20. (c) Hakimi, M.; Moeini, K.; Mardani, Z.; Schuh, E.; Mohr, F. Silver(I) coordination polymer and nine-coordinated cadmium(II) complex with dimethyl pyridine-2,6-dicarboxylate supported by solid state and electrochemical studies. J. Coord. Chem. 2013, 66, 1129. https://doi.org/10.1080/00958972.2013.775648
  21. (d) Hakimi, M.; Mardani, Z.; Moeini, K.; Mohr, F. Coordination behavior of dimethyl pyridine-2,6-dicarboxylate towards mercury(II), cadmium(II) and chromium(III) in the solid- and gaseous state supported by CSD studies. Polyhedron 2015, 102, 569. https://doi.org/10.1016/j.poly.2015.10.038
  22. (a) Hakimi, M.; Mardani, Z.; Moeini, K.; Mohr, F. Synthesis and characterization of a macrocyclic copper complex containing the 14-membered 1,3,5,8,10,12-hexaazacyclotetradecane unit. Z. Naturforsch 2017; Vol. 72b, p 115.
  23. (b) Hakimi, M.; Moeini, K.; Mardani, Z.; Fernandes, M. A.; Mohr, F.; Schuh, E. Template-directed synthesis of macrocyclic copper(II) complexes of diazacyclam, 1,3,6,10,12,15-hexaazatricyclo[13.3.1.16,10]eicosane. J. Coord. Chem. 2012, 65, 1232. https://doi.org/10.1080/00958972.2012.669834
  24. (c) Hakimi, M.; Moeini, K.; Mardani, Z.; Mohr, F. Microwave-assisted template synthesis of diazacyclam-based macrocyclic copper complex and forming octahedral, square planar and square pyramidal geometries by ion exchanging and introducing a novel 2D square-grid copper-mercury coordination polymer. Polyhedron 2014, 70, 92. https://doi.org/10.1016/j.poly.2013.12.033