Synthesis, characterization and crystal structure of a new tetraaza macrocycle with m-xylyl spacer

Document Type : Original Article


Applied Chemistry Department, Faculty of Science, Ardebil University of Mohaghegh, Ardebil


The new [2+2] macrocyclic ligand with N4 donor set, from the [2+2] condensation of benzene-1,3-dicarboxaldehyde and 2,2- dimethylpropylenediamine  was synthesized by high dilution method and confirmed by IR, 1H NMR, 13C NMR, elemental analysis and crystal structure determination. Resonance data investigation of the compound indicates highly symmetrical structure for the macrocyclic ligand consists of two N2 donor sets. The compound is crystallized in the monoclinic system with space group C2/c. The metric parameters of the molecule show that a twofold axis bisects the macrocycle, passing through the cavity of the macrocycle.


[1] D. E. Fenton, Chem. Soc. Rev. 28 (1999) 159.
[2] W. Radecka-Paryzek, V. Patroniak, J. Lisowski, Coord. Chem. Rev. 249 (2005) 2156.
[3] A. L. Vance, N. W. Alcock, D. H. Busch, J. A. Heppert, Inorg. Chem. 36 (1997) 5132.
[4] Z. Wang, J. Reibenspies, A. E. Martell Inorg. Chem. 36 (1997) 629.
[5] L. Cronin, P. A. McGregor, S. Parsons, S. Teat, R.O. Gould, V. A. White, N. J. Long, N. Robertson, Inorg. Chem. 43 (2004) 8023.
[6] B. Y. Lee, H. Y. Kwon, S. Y. Lee, S. J. Na, S. Han, H. Yun, H. Lee, Y. Park, J. Am. Chem. Soc.  127 (2005) 3031.
[7] U. Beckmann, S. Brooker, C. V. Depree,  J. D. Ewing, B. Moubaraki, K. S. Murray, J. Chem. Soc. Dalton Trans. (2003) 1308.
[8] H. Okawa, J. Nishio, M. Obha, M. Tadokoro, N. Matsumato, M. koikawa, S. kida, D. E. Fenton, Inorg. Chem. 32 (1993) 2949.
[9] J. J. Zhang, W. Zhang, Q. Luo, Y. H. Mei,  Polyhedron 18 (1999) 3637.
[10] Ph. G. Owston, R. Peters, , E. Ramsammy, P. A. Tasker, J. Trotter, J. Chem. Soc. Chem. Commun. (1980) 1218.
[11] K. Henrick, P. M. Judd, Ph. G. Owston, R. Peters, P. A. Tasker, R. W. Turner, J. Chem. Soc. Chem. Commun. (1983) 1253.
[12] A. A. Khandar, K. Kirschbaum, M. Abedi, K. Mock, G. Tracy, V. Spasojevic, NewJ. Chem., 2015 (39) 2822.
[13] P. Molenveld, J. F. J. Engbersen, D. N. Reinhoudt, chem. Soc. Rev. 29 (2000) 75.
[14] L. K. Thompson, S. K. Mandal, S. S. Tandon, J. N. Bridson, M. K. park, Inorg. Chem. 35 (1996) 3117.
[15] T. A. Kaden, Coord. Chem. Rev. 190-192 (1999) 371.
[16] U. Casellato, S. Tamburini, P. Tomasin, P. A. Vigato, S. Aime, M. Botta, Inorg. Chem. 38 (1999) 2906.
[17] S. R. Korupoju, N. Mangayarkarasi, S. Ameerunisha, E. J. Valente, P. S. Zacharias, J. Chem. Soc. Dalton Trans. (2000) 2845.
[18] R. Z. Liao, J. G. Yu, F. Himo, Inorg. Chem. 48 (2009) 1442.
[19] C. T. Liu, Al. A. Neverov, R. S. Brown, J. Am. Chem. Soc. 130( 2008) 13870.
[20] W.L.F. Armarego, D.D. Perrin, Purification of Laboratory Chemicals, Pergamon Press, Oxford, 1988.
[21] CrysAlis RED and CrysAlis CCD, Version, Oxford Diffraction Ltd., Abingdon, England, 2006.
[22] G.M. Sheldrick, SHELXL-97, Program for X-ray Crystal Structure Refinement, University of Göttingen, Göttingen, Germany, 1997.
[23] M. AbediK. KirschbaumA. N. ShamkhaliC. R. BrueA. A. Khandar, Polyhedron 109 (2016) 176.
[24] M. Abedi, A. N. Shamkhali, R. J. Butcher, A. A. Khandar, P. Garczarek, G. Mahmoudi, S. A. Hosseini-Yazdi, Polyhedron 119 (2016) 98.
]25[ حسینی صدر، موید، دانشگاه شهید مدنی آذربایجان، مجله شیمی کاربردی، شماره 38 (1395) ص 165.