3-tert-Butyl-1-(3-nitrophenyl)-1H-pyrazol-5-amine

Abstract

In the title compound, C13H16N4O2, the pyrazole ring forms a dihedral angle of 50.61 (6)° with the 3-nitro-phenyl ring. The plane of the nitro group is twisted by 6.8 (7)° out of the plane of the phenyl ring. In the crystal, the mol­ecules are linked by N—H⋯N and N—H⋯O hydrogen bonds, forming sheets in the bc plane. In addition, a weak C—H⋯N inter­action is observed.

Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN2(PhOH)CHN(C3N2(CH3)3)PhR, R = H or NO2)

“…The precursor pyrazoles (Pyr in Figure 3) were synthesized following the methodology reported in the literature [34,35]. A measure of 35.18 mmol of 4,4-dimethyl-3-oxopentanenitrile (dopn in Figure 3) and 35.18 mmol of phenylhydrazine (2-nitrophenylhydrazine, 3-nitrophenylhydrazine, 4-nitrophenylhydrazine) were mixed in an Erlenmeyer flask.…”

The Structure ofN‐phenyl‐pyrazoles and Indazoles: Mononitro, Dinitro, and Trinitro Derivatives

“…In the 3‐nitro derivatives, there are no coordinates available for 20 . For 21 , the NO 2 is on the same side as N2 (torsion angle 47.1°); N1 = 111.4°, N2 = 104.3°, Δθ = 7.1°.…”

“…The torsion angle increases with the bulkiness of the substituent at position 5, but the two "identical" halves of 18 have very different torsions.In the 3-nitro derivatives, there are no coordinates available for 20[309]. For 21[310], the NO 2 is on the same side as N2 (torsion angle 47.1°); N1 = 111.4°, N2 = 104.3°, Δθ = 7.1°.Excluding 29 (no coordinates available[127]), the remaining 17 structures show the following values:22 [311]: torsion = 31.5°; N1 = 111.3°, N2 = 104.6°, Δθ = 6.7°. 23 [173]: torsion = 39.8°; N1 = 113.8°, N2 = 103.8°, Δθ = 10.0°.…”