Reaction of 3-chloro-2,4-pentanedione with p-bromoaniline yields enaminone, 3-chloro-4-((4-bromophenyl)amino)pent-3-en-2-one. The structure of synthesized enaminone was identified by IR spectroscopy, proton NMR spectroscopy and single crystal X-ray crystallography. The enaminone was crystallized… Click to show full abstract
Reaction of 3-chloro-2,4-pentanedione with p-bromoaniline yields enaminone, 3-chloro-4-((4-bromophenyl)amino)pent-3-en-2-one. The structure of synthesized enaminone was identified by IR spectroscopy, proton NMR spectroscopy and single crystal X-ray crystallography. The enaminone was crystallized in monoclinic system with space group P21/c with cell coordinates a = 6.5123(4) Å, b = 12.1367(8) Å, c = 14.8002(9) Å, α = 90°, β = 93.512(2)°, γ = 90°, V = 1167.58(13) Å3, and Z = 4. Crystallographic analysis revealed that nitrogen and bromine atoms are in plane with aromatic ring. The aminopent-3-en-2-one chain forms a second plane and the angle between the two planes is observed to be 58.48°. Theoretical quantum chemical calculations have been performed on the studied enaminone using three different functionals—APFD, B3LYP & M06-2X. The geometric parameters of the optimized structure are in good agreement with experimental data obtained from X-ray structure.Graphical Abstract
Journal Title: Journal of Chemical Crystallography
Year Published: 2019
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