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Synthesis, Crystal Structure, Solution Study and In Silico ADME Profiling of Various Asymmetric Functionalized Triazenes

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Abstract

Syntheses of some ligands based on asymmetric triazenes consisting 1-(2-methoxycarbonylphenyl)-3-(2-methylphenyl)triazene (1), 1-(2-methoxycarbonylphenyl)-3-(3-methylphenyl)triazene (2), 1-(2-methoxycarbonylphenyl)-3-(4-methylphenyl)triazene (3), 1-(2-methoxycarbonylphenyl)-3-(3,5-dichlorophenyl)triazene (4), 1-(4-chlorophenyl)-3-(4-methylphenyl)-triazene (5) and their related HgII complexes were reported. The characterizations were performed by FT-IR, 1H NMR and 13C NMR spectroscopies. In (3) and (4), both triazenes possess trans-conformation around the (–N=N–) bond and monomeric moieties are linked to pairs and wave-like chains through C–H···O and C–H···N hydrogen bonds which are further assembled by stacking through secondary π···π interactions [3.829(1) and 3.736(1) Å]. The reaction of (1) and Hg(NO3)2 in methanol produces the corresponding HgII complex (6) where each triazenide binds to the HgII atom through two nitrogen atoms of triazenide and one oxygen atom of pendant methoxycarbonyl group forming distorted MN4O2 octahedral around the HgII atom. The stoichiometry and formation of complex (6) and (8) in methanol solution were investigated by UV–Vis titration. Moreover, Reaction of substituted 1,3-diaryltriazenes (2) and (5) with HgII salts afford a family of orange complexes (7) and (8), respectively. Finally, the chemical structures of the investigated ligands were correlated to their pharmacokinetic behaviour using five pre-calculated models implemented in VolSurf program.

Graphical Abstract

Polyhedron around HgII atom coordinated by two triazenide ligands in an octahedron fashion.

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Authors and Affiliations

  1. Faculty of Chemistry, Kharazmi University, Tehran, Iran

    Jafar Attar Gharamaleki, Atousa Goodarzi, Houra Sadat Bolouhari & Mohammad Kazem Rofouei

  2. Chemistry Department, Faculty of Science, Golestan University, Gorgan, Iran

    Shabnam Hooshmand

  3. Department of Chemistry, Shahid Beheshti University, G. C., Evin, 1983963113, Tehran, Iran

    Behrouz Notash

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  1. Jafar Attar Gharamaleki
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  2. Atousa Goodarzi
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Correspondence to Jafar Attar Gharamaleki.

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Attar Gharamaleki, J., Goodarzi, A., Bolouhari, H.S. et al. Synthesis, Crystal Structure, Solution Study and In Silico ADME Profiling of Various Asymmetric Functionalized Triazenes. J Inorg Organomet Polym 25, 892–905 (2015). https://doi.org/10.1007/s10904-015-0185-6

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