Journal of Chemistry

Journal of Chemistry / 2014 / Article

Research Article | Open Access

Volume 2014 |Article ID 619196 | 6 pages | https://doi.org/10.1155/2014/619196

Aluminum Dimer Containing Bulky 1,2,3-Triazolate Ligand

Academic Editor: Theocharis C. Stamatatos
Received27 Apr 2014
Revised15 Jun 2014
Accepted16 Jun 2014
Published17 Aug 2014

Abstract

The first molecular aluminum 1,2,3-triazolato complex was synthesized bearing a bulky 1,2,3-triazolate ligand. Oligomers and polymers were avoided due to the bulkiness and noncoordinating nature of the substituents. The novel Al2N4 ring formed contains symmetrical Al-N bond distances unexpectedly having asymmetric Al-N-N angles of 144.55(15)° and 115.83(14)°. This asymmetry demonstrates the effect of the steric hindrance of the ligand.

1. Introduction

There is considerable interest in the development of new molecular azolato metal complexes. Motivations in this area are diverse and include the preparation of new single-site olefin polymerization catalysts, attempts to understand and mimic hydrodenitrogenation catalysts, and the preparation of improved precursors to metal nitride phases, to name a few [1].

The chemistry of 3,5-disubstituted-1H-1,2,4-triazoles is dominated by polymeric complexes due to the presence of three donor sites on the triazole ring [229]. However, molecular complexes can also be synthesized [1, 3043]. On the other hand, the chemistry of 4,5-disubstituted-1H-1,2,3-triazoles is virtually nonexistent, with only very few molecular complexes isolated thus far [4446].

This scarcity can be attributed to several factors, mainly the difficulty in synthesizing 4,5-disubstituted-1H-1,2,3-triazole ligands with sufficient steric bulk to favor molecular complexes. Most of the attention in synthesizing 1,2,3-triazole ligands is given to the “click” chemistry approach due to its simplicity, versatility, and reputation for being a “green” process [4750]. Most click chemistry 1,2,3-triazole ligands contain an alkyl group bonded to one of the nitrogen atoms as a result of the use of organic azide as one of the reactants. The other reactant is usually a terminal alkyne that leaves one of the carbon atoms unsubstituted. The resulting triazole requires the cleavage of the N-C bond prior to use as an anionic ligand, or it can be used as a C-donor ligand. However, no click chemistry reaction has been able to synthesize a 4,5-disubstituted-1H-1,2,3-triazole ligand with noncoordinating side groups that is bulky enough to produce molecular complexes.

One reaction that has gone unnoticed is the deprotonation of trimethylsilyldiazomethane. This reaction can be further used in cycloaddition reactions to produce various 1,2,3-triazoles in fairly high yields. For example, trimethylsilyldiazomethanide can react with trimethylacetonitrile and upon acidification produce the very bulky ligand 4-tert-butyl-5-trimethylsilyl-1H-1,2,3-triazole (tzH) [45, 46, 51] (see Figure 1). Two complexes have been reported to contain this ligand formed in situ [45, 46]; however, no reactions have taken advantage of this bulky triazole in its isolated neutral form.

I hereby report the first aluminum complex bearing a 4,5-disubstituted-1,2,3-triazolate ligand. The complex is molecular, dimeric, and prepared by the reaction of trimethylaluminum (TMA) with free tzH. This reaction proves that sufficiently bulky 4,5-disubstituted-1H-1,2,3-triazole ligands can be used to synthesize new and interesting molecular complexes and should set the foundation to expand the study of the coordination of these poorly researched ligands. The complex synthesized in this report is the only 1,2,3-triazolato aluminum complex where the triazolato ligand is coordinated by virtue of the triazole core itself due to noncoordinating substituents. A previously reported 1,2,3-triazolato aluminum complex contains a triazolato ligand bearing coordinating phosphine chalcogenide substituents that dominate the coordination of the ligand [52, 53].

2. Experimental

2.1. General Considerations

All reactions were performed under an inert atmosphere of argon or nitrogen using either glovebox or Schlenk line techniques. Hexane was distilled from phosphorus pentoxide. THF was distilled from sodium/benzophenone. Al(CH3)3 was purchased from Strem Chemicals Inc. and used as received. Butyl lithium, trimethylacetonitrile, and trimethylsilyldiazomethane were purchased from Aldrich and used as received. 1H and 13C NMR were obtained at 500 MHz and 125 MHz, respectively. Elemental analysis was performed in house.

2.2. Preparation of Bis(μ-4-tert-butyl-5-trimethylsilyl-1,2,3-triazolato) (tetramethyl) Dialuminum (1)

TzH was prepared according to literature [51] and was used for the preparation of complex 1 as described below and illustrated in Figure 2. A 100 mL Schlenk flask was charged with tzH (0.4070 g, 2.062 mmol) and hexane (30 mL). Trimethylaluminum (0.1449 g, 2.010 mmol) was added and the solution was allowed to stir at room temperature for 18 h in the glovebox. The reaction mixture was then filtered through a pad of Celite, the volume was reduced to 5 mL, and the reaction mixture was allowed to stand undisturbed at −20°C. Complex 1 (0.6610 g, 63.25%) was isolated as colorless rods. Mp 139°C dec; 1H NMR (C6D6, 22°C, δ) 1.27 (s, 9 H, C(CH3)3), 0.59 (s, 9 H, Si(CH3)3); −0.50 (s, 12 H, Al(CH3)2; 13C NMR (C6D6, 22°C, δ) 150.01 (s, triazolate ring C-C), 136.82 (s, triazolate ring C-Si), 38.96 (s, C(CH3)3), 31.28 (s, C(CH3)3), −0.21 (s, Si (CH3)3), −8.31 (s, Al(CH3)2). Anal. calcd for C22H48Al2N6Si2: C, 52.14; H, 9.54; N, 16.58. Found: C, 53.18; H, 9.63; N, 16.25.

2.3. X-Ray Crystallographic Structure Determination

Diffraction data for 1 were measured on a Bruker diffractometer equipped with Mo radiation and a graphite monochromator. The samples were mounted in thin-walled glass capillaries under a dry nitrogen atmosphere. The frame data were indexed and integrated with the manufacturer’s SMART software [54]. All structures were refined using Sheldrick’s SHELX-97 software [55]. Hydrogen atom positions were calculated or observed.

3. Results and Discussion

3.1. Synthetic Parameters

Complex 1 was synthesized by reacting Al(CH3)3 and tzH in a 1 : 1 ratio. The reaction was clean and only one product was present as indicated by solid state structure and solution 1H NMR. Varying the ratio of Al(CH3)3 and tzH to 1 : 2 or 1 : 3 produced complex reaction mixtures as indicated by solution 1H NMR. These reactions were not further characterized. These mixtures could be due to incomplete protonation of the methyl groups resulting in tzH adducts or to equilibria between bridging and terminal complexes. A separate study is needed to determine the nature of these complexes and to optimize their synthesis.

3.2. X-Ray Crystal Structures

1 was characterized spectroscopically and structurally by single crystal X-ray diffraction. The composition was also verified by elemental analysis. All the atoms except the methyl groups lie in the same plane, with the two Al atoms being part of an Al2N4 6-membered ring. The space-filling model illustrates the steric hindrance provided by tz (see Figure 3).

Experimental crystallographic data are summarized in Table 1 and selected bond lengths and angles are presented in Tables 2 and 3. A representative perspective view of 1 is shown in Figure 4.


1
Empirical formula
Fw506.80
Space groupP2
  6.4680(8)
  15.477(2)
  15.599(2)
(deg)90.00
(deg)98.079(3)
(deg)90.00
  1546.0(4)
2
0.71073
(mm−1)0.191
0.0515
Rw0.1390


Al1–C81.945(3)Si1–C101.828(4)
Al1–C71.952(3)Al1–N21.966(2)
Al1–N31.972(2)Si1–C91.844(5)
Si1–C111.849(4)Si–C21.872(2)
N1–N21.327(3)N2–N31.337(3)
N1–C21.356(3)N3–C11.366(3)
N3–Al11.972(2)C1–C21.405(3)
C1–C31.604(3)C3–C51.523(5)
C3–C41.567(4)C3–C61.569(5)


C8–Al1–C7122.73(17)C8–Al1–N2104.69(12)
C8–Al1–N3112.10(14)N2–Al1–N399.58(8)
N2–N1–C2107.88(19)N1–N2–N3110.98(18)
N1–N2–Al1104.31(14)N3–N2–Al1144.55(15)
N2–N3–C1107.38(18)N2–N3–Al1115.83(14)
C1–N3–Al1136.69(16)N3–C1–C2106.7(2)
N3–C1–C3125.01(19)C2–C1–C3128.32(19)
N1–C2–C1107.1(2)N1–C2–Si1113.61(18)

The Al2N4 ring exhibits novel structure in that the Al-N distances are equal, yet the Al-N-N angles are asymmetric. The Al1-N2-N3 angle is 144.55(15)° and the Al1-N3-N2 angle is 115.83(14)° (see Figure 4).

This angular asymmetry is believed to be due to the Van der Waals repulsion between the bulky substituents and the alkyl groups on the Al. Figure 5 illustrates the proposed reason behind this asymmetry. Other aluminum azolato complexes with either pyrazoles, 1,2,4-triazoles, or tetrazoles that exhibit a similar Al2N4 ring structure do not exhibit this asymmetry [52, 5660]. Instead, the Al-N-N angles are symmetrical. This report thus demonstrates the novelty that can arise by using bulky 4,5-disubstituted-1H-1,2,3-triazole ligands such as tzH and illustrates the need to explore this accessible ligand further.

3.3. Thermogravimetric Analysis (TGA)

To identify the thermal stability of 1, TGA analysis was carried out on a Delta Series TA-SDTQ600 analyzer in a nitrogen atmosphere from room temperature to 700°C (10°C min−1) using aluminum crucibles (Figure 6). The result shows that the complex is stable up to 130°C, after which it begins to decompose steadily upon further heating. This is consistent with the observation of a decomposition point at around 139°C when measuring the melting point.

4. Conclusions

An unprecedented molecular aluminum complex containing the ligand tz was synthesized by virtue of the steric bulk and noncoordinating nature of the substituents. This steric bulk blocked the nitrogen atoms of the tz forming polymeric species. The complex exhibits a novel Al2N4 ring structure where the Al-N distances are the same but the Al-N-N angles vary greatly. These novel asymmetric angles are due to the Van der Waals repulsion between the bulky substituents and the alkyl groups on the aluminum. This report demonstrates the ease at which tzH can be accessed and the novelty that can arise when used to synthesize metal complexes. It should set the foundation for further research into the coordination of bulky 1,2,3-triazole ligands that are extremely scarce in the literature.

Conflict of Interests

The author declares that there is no conflict of interests regarding the publication of this paper.

Supporting Information

Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-969163. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).

Acknowledgment

The author is grateful for funding from the Petroleum Institute (RIFP Grant no. 12327).

References

  1. C. Yélamos, K. R. Gust, A. G. Baboul, M. J. Heeg, H. B. Schlegel, and C. H. Winter, “Early transition metal complexes containing 1,2,4-triazolato and tetrazolato ligands: Synthesis, structure, and molecular orbital studies,” Inorganic Chemistry, vol. 40, no. 25, pp. 6451–6462, 2001. View at: Publisher Site | Google Scholar
  2. Y. Fu and H. Lu, “In situ synthesis, structural characterization and luminescent property of a novel hybrid solid with twofold interpenetrating (4,6)-connected topology [{(Cu4I4)2H2O}{Cu6(mtz)6}]n (Hmtz = 3,5-dimethyl-1,2,4-triazole),” Journal of Molecular Structure, vol. 892, no. 1–3, pp. 205–209, 2008. View at: Publisher Site | Google Scholar
  3. X. Huang, T. Sheng, S. Xiang et al., “{[Cu(mtz)]3(Cul)}n: an unprecedented non-interpenetrated (123)(122·14)3 network with triple-stranded helices,” Inorganic Chemistry, vol. 46, no. 2, pp. 497–500, 2007. View at: Publisher Site | Google Scholar
  4. Y. Ling, Z.-X. Chen, Y.-M. Zhou, L.-H. Weng, and D.-Y. Zhao, “A novel green phosphorescent silver(I) coordination polymer with three-fold interpenetrated CdSO4-type net generated via in situ reaction,” CrystEngComm, vol. 13, no. 5, pp. 1504–1508, 2011. View at: Publisher Site | Google Scholar
  5. Y. Ling, F. Zhai, M. Deng et al., “Solvothermal in situ synthesis of cyanide-containing ternary silver(I) coordination polymers and their phosphorescent properties,” CrystEngComm, vol. 14, no. 4, pp. 1425–1431, 2012. View at: Publisher Site | Google Scholar
  6. N. Nijem, P. Canepa, U. Kaipa et al., “Water cluster confinement and methane adsorption in the hydrophobic cavities of a fluorinated metal-organic framework,” Journal of the American Chemical Society, vol. 135, no. 34, pp. 12615–12626, 2013. View at: Publisher Site | Google Scholar
  7. P. Ren, B. Ding, W. Shi, Y. Wang, T. Lu, and P. Cheng, “2D and 3D sulfate-water supramolecular networks templated via triazole-nickel(II) complexes,” Inorganica Chimica Acta, vol. 359, no. 12, pp. 3824–3830, 2006. View at: Publisher Site | Google Scholar
  8. B.-C. Tzeng and T.-Y. Chang, “Toward copper(I)-Iodide-based coordination architectures via N′,N′-bis(pyridylcarbonyl)-4,4′-diaminodiphenyl ether with different solvent compositions,” Crystal Growth & Design, vol. 9, no. 12, pp. 5343–5350, 2009. View at: Publisher Site | Google Scholar
  9. Y.-H. Wang, H. Xu, G. Yang, and H.-W. Hou, “3D binary copper(I) 3,5-dibutyl-1,2,4-triazolate: synthesis, structure and topology,” Journal of Chemical Crystallography, vol. 41, no. 3, pp. 434–437, 2011. View at: Publisher Site | Google Scholar
  10. D. Wu, B. Xia, F. Yang, L. Weng, and Y. Zhou, “A novel 3D Silver-triazolate coordination polymer with 6.102 topology: synthesis, crystal structure and phosphorescence,” Chinese Journal of Structural Chemistry, vol. 30, no. 5, pp. 685–689, 2011. View at: Google Scholar
  11. B. Xia, Z. Chen, Q. Zheng et al., “A flexible porous metal-azolate framework constructed by [Cu 3(μ3-OH)(μ2-O)(triazolate) 2]+ building blocks: synthesis, reversible structural transformation and related magnetic properties,” CrystEngComm, vol. 15, no. 17, pp. 3484–3489, 2013. View at: Publisher Site | Google Scholar
  12. C. Yang, U. Kaipa, Q. Z. Mather et al., “Fluorous metal-organic frameworks with superior adsorption and hydrophobic properties toward oil spill cleanup and hydrocarbon storage,” Journal of the American Chemical Society, vol. 133, no. 45, pp. 18094–18097, 2011. View at: Publisher Site | Google Scholar
  13. C. Yang, X. Wang, and M. A. Omary, “Fluorous metal-organic frameworks for high-density gas adsorption,” Journal of the American Chemical Society, vol. 129, no. 50, pp. 15454–15455, 2007. View at: Publisher Site | Google Scholar
  14. C. Yang, X. Wang, and M. A. Omary, “Crystallographic observation of dynamic Gas adsorption sites and thermal expansion in a breathable fluorous metal-organic framework,” Angewandte Chemie—International Edition, vol. 48, no. 14, pp. 2500–2505, 2009. View at: Publisher Site | Google Scholar
  15. G. Yang, P. Duan, K. Shi, and R. G. Raptis, “Relaying isomerism from ligands to metal complexes: synthesis and structures of four isomeric binary silver(I) 3,5-dibutyl-1,2,4-triazolates,” Crystal Growth and Design, vol. 12, no. 4, pp. 1882–1889, 2012. View at: Publisher Site | Google Scholar
  16. G. Yang and R. G. Raptis, “A robust, porous, cationic silver(I) 3,5-diphenyl-1,2,4-triazolate framework with a uninodal 49.66 net,” Chemical Communications, vol. 10, no. 18, pp. 2058–2059, 2004. View at: Publisher Site | Google Scholar
  17. G. Yang, P.-P. Zhang, L.-L. Liu, J.-F. Kou, H.-W. Hou, and Y.-T. Fan, “3D binary silver(I) 1,2,4-triazolates: Syntheses, structures and topologies,” CrystEngComm, vol. 11, no. 4, pp. 663–670, 2009. View at: Publisher Site | Google Scholar
  18. Q. Zhai, C. Lu, Q. Zhang et al., “Influence of substituents on the structures of hybrid complexes constructed from tetranuclear copper(I) 1,2,4-triazolate clusters and octamolybdates,” Inorganica Chimica Acta, vol. 359, no. 12, pp. 3875–3887, 2006. View at: Publisher Site | Google Scholar
  19. Q.-G. Zhai, M.-C. Hu, S.-N. Li, and Y.-C. Jiang, “Synthesis, structure and blue luminescent properties of a new silver(I) triazolate coordination polymer with 8210-a topology,” Inorganica Chimica Acta, vol. 362, no. 4, pp. 1355–1357, 2009. View at: Publisher Site | Google Scholar
  20. Q.-G. Zhai, X.-Y. Wu, S.-M. Chen, Z.-G. Zhao, and C.-Z. Lu, “Construction of Ag/1,2,4-triazole/polyoxometalates hybrid family varying from diverse supramolecular assemblies to 3-D rod-packing framework,” Inorganic Chemistry, vol. 46, no. 12, pp. 5046–5058, 2007. View at: Publisher Site | Google Scholar
  21. J.-P. Zhang and X.-M. Chen, “Exceptional framework flexibility and sorption behavior of a multifunctional porous cuprous triazolate framework,” Journal of the American Chemical Society, vol. 130, no. 18, pp. 6010–6017, 2008. View at: Publisher Site | Google Scholar
  22. J. Zhang and X. Chen, “Optimized acetylene/carbon dioxide sorption in a dynamic porous crystal,” Journal of the American Chemical Society, vol. 131, no. 15, pp. 5516–5521, 2009. View at: Publisher Site | Google Scholar
  23. J.-P. Zhang, Y.-Y. Lin, X.-C. Huang, and X.-M. Chen, “Supramolecular isomerism within three-dimensional 3-connected nets: Unusual synthesis and characterization of trimorphic copper(I) 3,5-dimethyl-1,2,4- triazolate,” Dalton Transactions, no. 22, pp. 3681–3685, 2005. View at: Publisher Site | Google Scholar
  24. J.-P. Zhang, Y.-Y. Lin, X.-C. Huang, and X.-M. Chen, “Copper(I) 1,2,4-triazolates and related complexes: Studies of the solvothermal ligand reactions, network topologies, and photoluminescence properties,” Journal of the American Chemical Society, vol. 127, no. 15, pp. 5495–5506, 2005. View at: Publisher Site | Google Scholar
  25. J. Zhang, S. Zheng, X. Huang, and X. Chen, “Two unprecedented 3-connected three-dimensional networks of copper(I) triazolates: in situ formation of ligands by cycloaddition of nitriles and ammonia,” Angewandte Chemie, vol. 43, no. 2, pp. 206–209, 2003. View at: Publisher Site | Google Scholar
  26. L. Zhang, Y. Ling, J. Li, and H. Gao, “Supramolecular self-assembly of two Cu(II) complexes with 1,2,4-triazole derivatives: syntheses, crystal structures and magnetic properties,” Structural Chemistry, vol. 19, no. 6, pp. 911–916, 2008. View at: Publisher Site | Google Scholar
  27. W.-H. Zhang, X.-B. Wei, P.-N. Jin, J.-F. Kou, and G. Yang, “Synthesis and crystal structures of silver(I) complexes of 3(5)-methyl-5(3)-phenyl-1H-1,2,4-triazole: two isomeric infinite chains coexisting in the same crystal,” Transition Metal Chemistry, vol. 36, no. 5, pp. 459–463, 2011. View at: Publisher Site | Google Scholar
  28. Z.-G. Zhao, R.-M. Yu, X.-Y. Wu et al., “One-pot synthesis of two new copper(i) coordination polymers: in situ formation of different ligands from 4-aminotriazole,” CrystEngComm, vol. 11, no. 11, pp. 2494–2499, 2009. View at: Publisher Site | Google Scholar
  29. A. Zhu, Q. Xu, F. Liu, and X. Qi, “Synthesis, characterization, and photoluminescence properties of a planar copper triazolate coordination polymer with cyanide as co-ligand,” Zeitschrift fur Anorganische und Allgemeine Chemie, vol. 637, no. 5, pp. 502–505, 2011. View at: Publisher Site | Google Scholar
  30. M. G. B. Drew, P. C. Yates, J. Trocha-Grimshaw, K. P. McKillop, and S. M. Nelson, “Oxidative nitrogen-nitrogen coupling of nitrites at a dicopper site and the structure of a pentanuclear copper-triazolyl complex containing two-co-ordinate and three-co-ordinate copper(I),” Journal of the Chemical Society, Chemical Communications, no. 5, pp. 262–263, 1985. View at: Google Scholar
  31. O. M. El-Kadri, M. J. Heeg, and C. H. Winter, “Synthesis, structural characterization, and properties of chromium(III) complexes containing amidinato ligands and η2-pyrazolato, η2-1,2,4-triazolato, or η1-tetrazolato ligands,” Dalton Transactions, no. 37, pp. 4506–4513, 2006. View at: Publisher Site | Google Scholar
  32. N. C. Mösch-Zanetti, M. Ferbinteanu, and J. Magull, “A new μ4-Oxo tetranuclear magnesium compound: coordination effects of the azolato ligands,” European Journal of Inorganic Chemistry, no. 4, pp. 950–956, 2002. View at: Google Scholar
  33. N. C. Mösch-Zanetti, M. Hewitt, T. R. Schneider, and J. Magull, “Titanium complexes containing bulky η5-1,2,4-triazolato ligands,” European Journal of Inorganic Chemistry, no. 5, pp. 1181–1185, 2002. View at: Google Scholar
  34. F. J. Rietmeijer, J. G. Haasnoot, A. J. Den Hartog, and J. Reedijk, “Synthesis, spectroscopic and magnetic properties of linear nickel(II) and cobalt(II) trimers containing substituted 1,2,4-triazoles and fluoride as bridging ligands. The X-ray structure of bis [(μ-fluoro)bis(μ-3, 4, 5-trimethyl-1,2, 4-triazole-N1,N2)bis-(thiocyanato-N)(aqua)cobalt(II)-F,N1,N1′] cobalt(II) tetrahydrate,” Inorganica Chimica Acta, vol. 113, no. 2, pp. 147–155, 1986. View at: Publisher Site | Google Scholar
  35. F. J. Rietmeijer, G. A. van Albada, R. A. G. de Graaff, J. G. Haasnoot, and J. Reedijk, “Linear trinuclear transition-metal compounds containing 3,5-diethyl-1,2,4-triazole and fluoride as bridging ligands. X-ray structure of bis[(μ-fluoro)bis(μ-3,5-diethyl-1,2,4-triazole-N1,N 2)bis(thiocyanato-N)(3,5-diethyl-1,2,4-triazole-N1′)cobalt(II)-F,N1,N1]cobalt(II) dihydrate,” Inorganic Chemistry, vol. 24, no. 22, pp. 3597–3601, 1985. View at: Publisher Site | Google Scholar
  36. W.-Z. Shen, F. Kang, Y.-J. Sun et al., “The synthesis and crystal structure of [M{H2B(tz)2}2(H2O)] (M = Cu, Zn and tz = 3,5-dimethyl-1,2,4-triazole),” Inorganic Chemistry Communications, vol. 6, no. 4, pp. 408–411, 2003. View at: Publisher Site | Google Scholar
  37. G. A. van Albada, R. A. G. de Graaff, J. G. Haasnoot, and J. Reedijk, “Synthesis, spectroscopic characterization, and magnetic properties of unusual 3,5-dialkyl-1,2,4-triazole compounds containing N-bridging isothiocyanato ligands. X-ray structure of trinuclear bis[(μ-thiocyanato-N)bis(μ-3,5-diethyl-1,2,4-triazole-N1,N 2)bis(thiocyanato-N)(3,5-diethyl-1,2,4-triazole-N 1)nickel(II)-N,N1,N1']nickel(II) dihydrate,” Inorganic Chemistry, vol. 23, no. 10, pp. 1404–1408, 1984. View at: Publisher Site | Google Scholar
  38. Z. Y. Wang, Y.L. Wang, G. Yang, and S. W. Ng, “Bis(μ2-3,5-diisopropyl-4H-1,2,4-triazole-2 N 1:N 2)bis-[(nitrato-κO)silver(I)],” Acta Crystallographica E: Structure Reports Online, vol. 65, no. 8, p. m974, 2009. View at: Publisher Site | Google Scholar
  39. Z. Xiao, M. A. Bruck, C. Doyle et al., “Dioxomolybdenum(VI) complexes of tripodal nitrogen-donor ligands: syntheses and spectroscopic, structural, and electrochemical studies, including the generation of EPR-active molybdenum(V) species in solution,” Inorganic Chemistry, vol. 34, no. 24, pp. 5950–5962, 1995. View at: Publisher Site | Google Scholar
  40. Z. Xiao, R. W. Gable, A. G. Wedd, and C. G. Young, “The cis-dioxomolybdenum(V) radical anion, [{HB(Me2C 2N3)3}MoO2(SPh)],” Journal of the Chemical Society, Chemical Communications, no. 11, pp. 1295–1296, 1994. View at: Publisher Site | Google Scholar
  41. Z. Xiao, R. W. Gable, A. G. Wedd, and C. G. Young, “Complexes containing cis-[MoVO2]+ and cis-[MoVO(OH)]2+ centers,” Journal of the American Chemical Society, vol. 118, no. 12, pp. 2912–2921, 1996. View at: Publisher Site | Google Scholar
  42. C. Yang, M. Messerschmidt, P. Coppens, and M. A. Omary, “Trinuclear gold(I) triazolates: a new class of wide-band phosphors and sensors,” Inorganic Chemistry, vol. 45, no. 17, pp. 6592–6594, 2006. View at: Publisher Site | Google Scholar
  43. Z. Yanga, L. Tang, X. Ma, J. Wang, J. Wu, and L. Wang, “Group 6 metal carbonyl complexes containing the 3,5-dimethyl-1,2, 4-triazole ligand,” Journal of Chemical Research S, no. 8, pp. 495–496, 2003. View at: Google Scholar
  44. J. A. Krause Bauer, T. M. Becker, and M. Orchin, “The preparation and crystal structures of some tricarbonylmanganese(I) octahedral complexes containing the 1,1-dimethylamino-2,2- diphenylphosphinoethane ligand,” Journal of Chemical Crystallography, vol. 34, no. 12, pp. 843–849, 2004. View at: Publisher Site | Google Scholar
  45. G. Boche, J. C. W. Lohrenz, and F. Schubert, “Lithio-diazomethane and lithio-(trimethylsilyl)diazomethane: theoretical and experimental studies of their structures, reactions and reaction products,” Tetrahedron, vol. 50, no. 20, pp. 5889–5902, 1994. View at: Publisher Site | Google Scholar
  46. W. Rigby, P. M. Bailey, J. A. McCleverty, and P. M. Maitlis, “Pentamethylcyclopentadienyl-rhodium and -iridium complexes. Part 19. Preparation and reactions of azido-, cyanato-, thiocyanato-, nitrito-, and nitrato-rhodium complexes,” Journal of the Chemical Society, Dalton Transactions, no. 2, pp. 371–381, 1979. View at: Publisher Site | Google Scholar
  47. H. C. Kolb, M. G. Finn, and K. B. Sharpless, “Click chemistry: diverse chemical function from a few good reactions,” Angewandte Chemie International, vol. 40, pp. 2004–2021, 2001. View at: Google Scholar
  48. J. E. Hein and V. V. Fokin, “Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides,” Chemical Society Reviews, vol. 39, no. 4, pp. 1302–1315, 2010. View at: Publisher Site | Google Scholar
  49. H. Struthers, T. L. Mindt, and R. Schibli, “Metal chelating systems synthesized using the copper(I) catalyzed azide-alkyne cycloaddition,” Dalton Transactions, vol. 39, no. 3, pp. 675–696, 2010. View at: Publisher Site | Google Scholar
  50. M. Meldal and C. W. Tomøe, “Cu-catalyzed azide-Alkyne cycloaddition,” Chemical Reviews, vol. 108, no. 8, pp. 2952–3015, 2008. View at: Publisher Site | Google Scholar
  51. A. R. Barron, “Meldola lecture: reactions of group 13 alkyls with dioxygen and elemental chalcogens: from carelessness to chemistry,” Chemical Society Reviews, vol. 22, no. 2, pp. 93–99, 1993. View at: Publisher Site | Google Scholar
  52. J. Alcántara-García, V. Jancik, J. Barroso et al., “Coordination diversity of aluminum centers molded by triazole based chalcogen ligands,” Inorganic Chemistry, vol. 48, no. 13, pp. 5874–5883, 2009. View at: Publisher Site | Google Scholar
  53. A. L. Rheingold, L. M. Liable-Sands, and S. Trofimenko, “4, 5-Bis(dipheylphosphinoyl)-1, 2, 3-triazole: a powerful new ligand that uses two different modes of chelation,” Angewandte Chemie (International Edition), vol. 39, pp. 3321–3324, 2000. View at: Google Scholar
  54. “SMART, SAINT, SADABS, and APEX-II collection and processing programs are distributed by the manufacturer,” Bruker AXS Inc., Madison, Wis, USA. View at: Google Scholar
  55. G. Sheldrick, SHELX-97, University of Götting, Göttingen, Germany, 1997.
  56. C. T. Sirimanne, Z. Yu, M. J. Heeg, and C. H. Winter, “Synthesis, structure, and bridge-terminal alkyl exchange kinetics of pyrazolate-bridged dialuminum complexes containing bridging n-alkyl groups,” Journal of Organometallic Chemistry, vol. 691, no. 11, pp. 2517–2527, 2006. View at: Publisher Site | Google Scholar
  57. S. A. Cortes-Llamas, J. M. Hernández-Pérez, M. Hô, and M.-Á. Muñoz-Hernández, “Indazolato derivatives of boron, aluminum, and gallium: characterization and solvent-dependent regioisomeric structures through π-π interactions in the solid state,” Organometallics, vol. 25, no. 3, pp. 588–595, 2006. View at: Publisher Site | Google Scholar
  58. W. Zheng, H. Hohmeister, N. C. Mösch-Zanetti, H. W. Roesky, M. Noltemeyer, and H.-G. Schmidt, “Syntheses and characterization of μ,η1,η1-3,5-di-tert-butylpyrazolato derivatives of aluminum,” Inorganic Chemistry, vol. 40, no. 10, pp. 2363–2367, 2001. View at: Publisher Site | Google Scholar
  59. J. Lewiński, J. Zachara, T. Kopeć, I. Madura, and I. Prowotorow, “On the mechanism of four-coordinate aluminum alkyls interaction with dioxygen: evidence for spatial demands in the autoxidation reaction,” Inorganic Chemistry Communications, vol. 2, no. 4, pp. 131–134, 1999. View at: Publisher Site | Google Scholar
  60. M. Muñoz-Hernández, M. S. Hill, and D. A. Atwood, “Syntheses and reactions of tetrazole-group 13 complexes,” Polyhedron, vol. 17, no. 13-14, pp. 2237–2242, 1998. View at: Publisher Site | Google Scholar

Copyright © 2014 Issam Kobrsi. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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