107155-23-7Relevant academic research and scientific papers
Z/E -Isomerism of 3-[4-(dimethylamino)phenyl]-2-(2,4,6-tribromophenyl)acrylonitrile: Crystal structures and secondary intermolecular interactions
Tammisetti, Renuka Devi,Kosilkin, Ilya V.,Guzei, Ilia A.,Khrustalev, Victor N.,Dalton, Larry,Timofeeva, Tatiana V.
, p. 69 - 74 (2018)
The Z and E isomers of 3-[4-(dimethylamino)phenyl]-2-(2,4,6-tribromophenyl)acrylonitrile, C 17 H 13 Br 3 N 2, (1), were obtained simultaneously by a Knoevenagel condensation between 4-(dimethylamino)benzaldehyde and 2-(2,4,6-tribromophenyl)acetonitrile, and were investigated by X-ray diffraction and density functional theory (DFT) quantum-chemical calculations. The (Z)-(1) isomer is monoclinic (space group P2 1 /n, Z′ = 1), whereas the (E)-(1) isomer is triclinic (space group P, Z′ = 2). The two crystallographically-independent molecules of (E)-(1) adopt similar geometries. The corresponding bond lengths and angles in the two isomers of (1) are very similar. The difference in the calculated total energies of isolated molecules of (Z)-(1) and (E)-(1) with DFT-optimized geometries is ～4.47 kJ mol -1, with the minimum value corresponding to the Z isomer. The crystal structure of (Z)-(1) reveals strong intermolecular nonvalent Br?N [3.100 (2) and 3.216 (3) ?] interactions which link the molecules into layers parallel to (10). In contrast, molecules of (E)-(1) in the crystal are bound to each other by strong nonvalent Br?Br [3.5556 (10) ?] and weak Br?N [3.433 (4) ?] interactions, forming chains propagating along [110]. The crystal packing of (Z)-(1) is denser than that of (E)-(1), implying that the crystal structure realized for (Z)-(1) is more stable than that for (E)-(1).
