Abstract
The title compound (E)-1,3-dimethyl-2-[3-(4-nitro-phen-yl)triaz-2-enyl-idene]-2,3-di-hydro-1H-imidazole, C11H12N6O2, has monoclinic (C2/c) symmetry at 100 K. This triazene derivative was synthesized by the coupling reaction of 1,3-di-methyl-imidazolium iodide with 1-azido-4-nitro benzene in the presence of sodium hydride (60% in mineral oil) and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The mol-ecule consists of six-membered and five-membered rings, which are connected by a triazene moiety (-N=N-N-). In the solid-state, the mol-ecule is found to be planar due to conjugation throughout the mol-ecule. The extended structure shows two layers of mol-ecules, which present weak inter-molecular inter-actions that facilitate the stacked arrangement of the mol-ecules forming the extended structure. Furthermore, there are several weak pseudo-cyclical inter-actions between the nitro oxygen atoms and symmetry-adjacent H atoms, which help to arrange the mol-ecules.
Highlights
Triazenes are versatile compounds in preparative chemistry because of their stable and highly modular nature (Patil & Bugarin, 2016)
Triazene derivatives have been studied for their potential anticancer properties (Rouzer et al, 1996; Connors et al, 1976), used as a protecting group in natural product synthesis (Nicolaou et al, 1999) and combinatorial chemistry (Brase et al, 2000), incorporated into polymers (Jones et al, 1997) and oligomer synthesis (Moore, 1997), and used to prepare heterocycles (Wirschun et al, 1998)
Their modular nature allows triazenes to be converted into a different functional group after treatment with the appropriate reagents
Summary
Triazenes are versatile compounds in preparative chemistry because of their stable and highly modular nature (Patil & Bugarin, 2016). Triazene derivatives have been studied for their potential anticancer properties (Rouzer et al, 1996; Connors et al, 1976), used as a protecting group in natural product synthesis (Nicolaou et al, 1999) and combinatorial chemistry (Brase et al, 2000), incorporated into polymers (Jones et al, 1997) and oligomer synthesis (Moore, 1997), and used to prepare heterocycles (Wirschun et al, 1998). Unique transformations of triazabutadienes have been affected via water solubility, pH (Kimani & Jewett, 2015; Guzman et al, 2016; He et al, 2017), and photoinduced isomerization (He et al, 2015) In synthesis, these triazenes have been used as starting materials for aldehydes, ketones, ethers, and sulfides, under mild reaction conditions (Barragan & Bugarin, 2017; Cornali et al, 2016). The C—C—C bond angles are around 120, with the variation being less than 2, which is characteristic of sp2hybridized carbons
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