2-Anilinomethylene-3-oxobutanenitrile: an X-ray and density functional theory study

Abstract

Molecules of the title compound, C11H10N2O, are effectively planar. In the crystal structure, they are stabilized primarily by electrostatic interactions, as the dipole moment of the molecule is 4.56 D. In addition, the molecules are linked by weak C-H...N and C-H...O hydrogen bonds. An analysis of bonding conditions in the molecule was carried out using natural bond orbital (NBO) formalism.

(E)-Methyl 2-anilinomethylene-3-oxobutanoate: X-ray and density functional theory studies

“…4. A similar electronic redistribution was found in 2-anilinomethylene-3-oxobutanenitrile (Langer et al, 2006) and in 5-anilinomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione (Smrc Ïok et al, 2007).…”

2-{[(3-Fluorophenyl)amino]methylidene}-3-oxobutanenitrile and 5-{[(3-fluorophenyl)amino]methylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione: X-ray and DFT studies

“…Heteroarylaminoethylene compounds substituted with fluorine are not only excellent precursors for the synthesis of biologically active 4-quinolones, but they are also biologically active themselves as they show, for example, photobleaching activity towards cells of Nicotiana tabacum, and fungicidal, germicidal or herbicidal properties. The title compounds were synthesized within the framework of our ongoing study (Langer et al, 2006(Langer et al, , 2009Smrčok et al, 2007) of the structure and properties of potential precursors of fluoroquinolones, knowledge of which has proven essential in reaction pathway considerations and planning.…”

(E)-3-Dimethylamino-2-(1H-indol-3-ylcarbonyl)acrylonitrile: a chain of edge-fused rings built from a three-centre N—H...(N,O) hydrogen bond

“…We report here the structure of (I) for comparison with three closely-related amino-substituted derivatives, viz. (II) [Cambridge Structural Database (Allen, 2002) refcode LEMSUS (Hashmi et al, 2006)], (III) (AMIMZF10; Adhikesavalu & Venkatesan, 1981) and (IV) (PELZUC; Langer et al, 2006), as well as with the thienyl analogues (V)-(IX) (Cobo et al, 2005;Cobo, Quiroga et al, 2006;.…”

“…In the crystal structures of (II) (Hashmi et al, 2006) and (III) (Adhikesavalu & Venkatesan, 1981), both close related to (I), there are no significant direction-specific intermolecular interactions of any kind, and neither the carbonyl O atoms nor the nitrile N atoms act as hydrogen-bond acceptors. In (IV) (Langer et al, 2006), there is an intermolecular N-HÁ Á ÁO hydrogen bond; while the original report of this compound listed intermolecular C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds, no analysis or discussion of the resulting supramolecular aggregation was provided. Analysis of this structure using the published atomic coordinates shows that the molecules are linked into sheets lying parallel to (101) and built from alternating centrosymmetric R 2 2 (10) and R 6 6 (38) rings (Fig.…”

“…A stereoview of part of the crystal structure of (IV), showing the formation of a hydrogen-bonded sheet parallel to (101). The original atomic coordinates (Langer et al, 2006) have been used and, for the sake of clarity, H atoms not involved in the motifs shown have been omitted.…”