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BOUROSH, Paulina; KRAVTSOV, Viktor; BACHINSKII, Sergey; PAVLOVSKY, Victor; ANDRONATI, Serghei. (E)-1-(2-aminophenyl)-3-phenylprop-2-en-1-ones: synthesis and structure of new polymorph. In: Materials Science and Condensed Matter Physics. Ediția a 9-a, 25-28 septembrie 2018, Chișinău. Chișinău, Republica Moldova: Institutul de Fizică Aplicată, 2018, p. 152.
|Materials Science and Condensed Matter Physics
Ediția a 9-a, 2018
Conferința "International Conference on Materials Science and Condensed Matter Physics" |
Chișinău, Moldova, 25-28 septembrie 2018
1,3-Diphenyl-2-propen-1-ones show antimicrobial, antifungal, antitumor, antioxidant, cytotoxic, antiproliferative, anti-inflammatory, hepatoprotective and other types of activities. They also serve as precursors for the synthesis of a number of biologically active compounds. Condensation of 2- aminoacetophenone with aromatic aldehydes yielded a series of (E)-1-(2-aminophenyl)-3- phenylprop-2-en-1-ones. The structure of compounds 2-7 was confirmed by mass spectrometry and 1H-NMR spectroscopy, and for (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one 5 also by the single crystal X-ray diffraction. NH2 O R NH2 O CH3 Ar O EtOH, KOH 1 R = H (2), OCH3 (3), F (4), Cl (5), Br (6), NO2 (7) 2 - 7 The compound 5 crystallizes in the monoclinic P21/c space group, a=8.459(2), b=6.729(1), c=21.996(3) Å; β=106.429(5)o, V=1249.7(4)Å3, Z=4 with one molecule per asymmetric unit (Z‘=1) in contrast to the recently published orthorhombic polymorph (sp.gr. P212121, Z=8, Z‘=2) . The molecule is planar within 0.18Å. The C-C bond distances adjust the common values, the C=O1, C-N1, and C-Cl1 bond distances are equal to 1.234(4), 1.355(5) and 1.733(3) Å, respectively. The C=C double bond is equal to 1.307(4) Å. The conformation of the molecule is stabilized by intramolecular N-H…O = 2.627Å hydrogen bond. In the crystal the neighboring center-symmetry related molecules reside in parallel planes with interplanar separation 3.446 Å and are coupled due to arene–alkene π-stacking interactions . The distances from the centroid of the aromatic ring to the midpoint of the C=C double bond equals 3.484 Å. Such dimeric associates further interact via C-H…O = 3.392 Å bonds resulting in formation of ribbon along crystallographic axis b.