Synthesis and X-ray Crystal Structure of N’-Cyano-N,N’-dimethyl-4-nitrobenzohydrazide

Abstract

Using a two-step procedure, N'-cyano-N,N'-dimethyl-4-nitrobenzohydrazide was synthesized. The structure was established using single crystal X-ray diffraction. It crystalized in the orthorhombic space group P2 1 2 1 2 1 where a = 8.1974(6), b = 10.6696(7), and c = 12.9766(8) Å. The first reported crystal structure of an acyclic cyanohydrazide is discussed with a focus on the geometry of the hydrazide moiety, but intermolecular contacts in the crystal are also considered.

Azanitrile Inhibitors of the SmCB1 Protease Target Are Lethal to Schistosoma mansoni: Structural and Mechanistic Insights into Chemotype Reactivity

“…The bound 3a adopts the Z -configuration as seen in the SmCB1– 3a crystallographic complex; however, the modeling of unbound 3a reveals that the E -configuration is more stable in solvent (by 1.9 kcal mol –1 ) (Table S6 and Figure S3). This is in line with the preferred E -conformation determined experimentally for other free azanitriles and trisubstituted hydrazides in general. ,,, Thus, 3a undergoes a conformational change upon binding to the enzyme. The activation energy for the E - to Z -conversion calculated using the implicit solvent model was approximately 15 kcal mol –1 (Table S6).…”

“…This is in line with the preferred E -conformation determined experimentally for other free azanitriles and trisubstituted hydrazides in general. 33 , 34 , 40 , 41 Thus, 3a undergoes a conformational change upon binding to the enzyme. The activation energy for the E - to Z -conversion calculated using the implicit solvent model was approximately 15 kcal mol –1 ( Table S6 ).…”

“…This is in line with the preferred E-conformation determined experimentally for other free azanitriles and trisubstituted hydrazides in general. 33,34,40,41 Thus, 3a under-goes a conformational change upon binding to the enzyme.…”

Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-aroyl-N′-(4′-cyanophenyl)thioureas

“…The carbon atoms of the thiocarbonyl group (C=S) at δ C 179.8 ppm and 179.4 ppm for the compounds 1 and 2 were showed the highest values, whereas the signals of carbonyl groups (C=O) at 168.6 and 167.0 ppm also appeared more de-shielded in the NMR spectra, respectively. The carbon signal of the nitrile group generally appears at δ C 110-120 ppm, downfield from TMS [23]. From the 13 C-NMR spectrums, the characteristic -C≡N signals appeared at δ C 119.2 and 119.1 ppm for the compounds 1 and 2, respectively.…”

“…downfield from TMS [23]. From the 13 C-NMR spectrums, the characteristic -C≡N signals appeared at δC 119.2 and 119.1 ppm for the compounds 1 and 2, respectively.…”