Abstract
In this work, the asymmetric ligands [1-(phenyl)-3-(2-nitro-4-methylphenyl)]triazene (1), [1-(4- methylphenyl)-3-(2-nitro-4-methylphenyl)]triazene (2), [1-(4-ethylphenyl)-3-(2-nitro-4-methylphenyl)]triazene (3) and [1-(4-ethoxyphenyl)-3-(2-nitro-4-methylphenyl)]triazene (4), were synthesized. The reaction of the ligand (3) with HgCl 2 in methanol resulted in the formation of the [HgL 2] complex, (5). All compounds were characterized by means of CHN analysis, FT-IR, 1H NMR, 13C NMR spectroscopy. In addition, the crystal structures of the ligands (2) to (4) were investigated by single crystal X-ray analysis. In the solid state, all ligands exhibited trans conformation about the –N =N– double bond. The Hg II complex (5) crystallized in monoclinic system with C2/c space group. The triazene ligand was found to be deprotonated prior to coordination and acts as monodentate ligand. The Hg II which lies on inversion center (site symmetry ı̄), is surrounded by two N atoms from L ligands forming a linear geometry. The other two Hg–N bonds are relatively longer and can only be regarded as weak secondary bonds. Also, Hg- η 3-arene π-interactions are present in this compound. Hydrogen bonds, π⋯π and C–H ⋯π stacking interactions help in the stabilization of the resulted frameworks. These C–H ⋯π edge-to-face interactions are present with H ⋯π distance of 3.00 Å.
Synthesis, characterization and X-Ray crystal structures of a few asymmetric triazenes with (–NH–N=N–) moieties and a linear HgII complex (HgL 2) with Hg...π secondary bonding interactions are described.
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References
De Oliveira G M, Horner M, Machado A, Back D F, Monteiro J H S K and Davolos M R 2011 Inorg. Chim. Acta 366 203
Zhao Y, Cao Q E, Hu Z and Xu Q 1999 Anal. Chim. Acta 388 45
Jean-Claude B J, Mustafa A, Damian Z, De Marte J, Vasilescu D E, Yen R, Chan T H and Layland-Jones B 1999 Biochem. Pharmacol. 57 753
Rudolf M F, Ciunik Z, Gatner K and Wolny J A 1992 Polyhedron 11 2591
Aneetha H, Padmaja J and Zacharias P S 1996 Polyhedron 15 2445
Leman J T, Wilking J B, Cooling A J and Barron A R 1993 Inorg. Chem. 32 4324
Vrieze K and Van Koten G 1987 In Comprehensive Coordination Chemistry (Oxford: Pergamon Press) p. 189
Moore D S and Robinson S D 1986 Adv. Inorg. Chem. Radiochem. 28 1
Horner M, Carratu V S, Bordinhao J, Silva A and Niquet E 2004 Acta Crystallogr. Sect. C 60 m140
Horner M, Bortoluzzi A J, Beck J and Serafin M 2002 Z Anorg. Allg. Chem. 628 1104
Horner M, Manzoni de Oliveira G, Bonini J S and Fenner H 2006 J. Organomet. Chem. 691 655
Desiraju G R 2011 Angew. Chem. Int. Ed. Engl. 50 5590
Roesky H W and Andruh M 2003 Coord. Chem. Rev. 236 91
Biradha K 2003 CrystEngComm 5 374
Chen X M and Liu G F 2002 Chem. Eur. J. 8 4811
Batten S R, Hoskins B F and Robson R 1995 J. Am. Chem. Soc. 117 5385
Gardner G B, Venkataraman D, Moore J S and Lee S 1995 Science 374 792
Hoskins B F and Robson R 1990 J. Am. Chem. Soc. 112 1546
Rofouei M K, Shamsipur M and Payehghadr M 2006 Anal. Sci. 22 x79
Rofouei M K, Melardi M R, Salemi Y and Kazemi S R 2009 Acta Crystallogr. Sect. E 65 o719
Melardi M R, Khalili Ghaydari H R, Barkhi M and Rofouei M K 2008 Anal. Sci. 24 x281
Melardi M R, Aghamohamadi M, Attar Gharamaleki J, Rofouei M K and Notash B 2012 Acta Crystallogr. Sect. E 68 o724
Melardi M R, Ghannadan A, Peyman M, Bruno G and Amiri Rudbari H 2011 Acta Crystallogr. Sect. E 67 o3485
Melardi M R, Rofouei M K and Massomi J 2007 Anal. Sci. 23 x67
Hematyar M and Rofouei M K 2008 Anal. Sci. 24 x117
Rofouei M K, Hematyar M, Ghoulipour V and Attar Gharamaleki J 2009 Inorg. Chim. Acta 362 3777
Melardi M R, Salemi Y, Razi Kazemi S and Rofouei M K 2009 Acta Crystallogr. Sect. E 65 m302
Rofouei M K, Ghalami Z, Attar Gharamaleki J, Ghoulipour V, Bruno G and Amiri Rudbari H 2012 Z. Anorg. Allg. Chem. 638 798
Rofouei M K, Attar Gharamaleki J, Fereyduni E, Aghaei A, Bruno G and Amiri Rudbari H 2012 Z. Anorg. Allg. Chem. 638 220
Rofouei M K, Attar Gharamaleki J, Melardi M R, Hosseini S M, Hosseinzadeh F, Peyman M, Ghannadan A, Notash B, Bruno G and Amiri Rudbari H 2012 Polyhedron 44 138
Stoe and Cie 2005 X–AREA: Program for the Acquisition and Analysis of Data, Version 1.30 (Darmstadt, Germany: Stoe & Cie GmbH)
Stoe and Cie 2005 X–RED: Program for Data Reduction and Absorption Correction, Version 1.28b (Darmstadt, Germany: Stoe & Cie GmbH)
Stoe and Cie 2004 X–SHAPE: Program for Crystal Optimization for Numerical Absorption Correction, Version 2.05 (Darmstadt, Germany: Stoe & Cie GmbH)
Sheldrick G M 1997, SHELX97 Program for Crystal Structure Solution (Göttingen Germany: University of Göttingen)
Sheldrick G M 1997 SHELX97 Program for Crystal Structure Refinement (Göttingen Germany: University of Göttingen)
International Tables for X-ray Crystallography, Vol C 1995 (Dordrecht, The Netherlands: Kluwer Academic Publisher)
Stoe and Cie 2000 X-STEP32: Crystallographic Package Version 1.07b (Darmstadt, Germany: Stoe & Cie GmbH)
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CCDC 1008066, 1008067, 1008068 and 1008069 contain the supplementary crystallographic data for compounds (2) to (5), respectively. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/ conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+ 44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk.
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MELARDI, M.R., SHAMSI MOGOII, F.B., SAJIRANI, A.B. et al. Synthesis, characterization and crystal structure of four new asymmetric triazene ligands: An example of linear HgII complex with Hg... π secondary bonding interactions. J Chem Sci 127, 2171–2181 (2015). https://doi.org/10.1007/s12039-015-0979-7
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DOI: https://doi.org/10.1007/s12039-015-0979-7