Synthesis
and characterization of substituted 2,6-dibenzylidene
cyclohexanone-based bischalcone derivatives and their optimized geometries
were investigated by density functional theory. The synthesized compounds
were identified through ultraviolet–visible, Fourier transform
infrared, and
1
H nuclear magnetic resonance spectroscopies
and elemental analysis. Significant acidochromic behavior was observed
for 2,6-bis(4-dimethylamino-benzylidene)-cyclohexanone
1e
. This result is owing to the preferential protonation of the chromophoric
N
,
N
-dimethylamino group, that is, quaternary
salt formation and deactivation of the resonance system. The result
was consistent with computational studies where the protonation was
favored by 211 kcal/mol in the gas phase. The compounds also showed
solvatochromic behavior. The geometries of the synthesized compounds
were optimized with B3LYP/6-311G+(d,p) and APFD/6-311+G(d,p) basis
sets. The single point energy indicated that APFD/6-311+G(d,p) basis
set gave the lowest energy of 445–655 kcal/mol for the studied
bischalcone derivatives. Quantum chemical parameters were also calculated.
Benzopyran derivatives R 0350 Synthesis of Substituted and Unsubstituted 2,4-Diaryl-5-oxo-5,6,7,8-tetrahydro-2-chromens. -[via Zn(II)-mediated condensation of arylideneacetophenones (II) with cyclohexanediones (I)]. -(AHMED*, M. G.; AHMED, S. A.; ROMMAN, U. K. R.; TOUCHY, A. S.; BADAL, M. R.; HOSSAIN, M. A.; UDDIN, M. K.; Indian J.
Several chalcones viz. 1,3-diaryl-2-propane-1-one (1a), 3-(4-hydroxy phenyl)-1-phenyl-2-propane-1-
one (1b), 3-(4-amino-phenyl)-1-phenyl-2-propane-1-one (1c) and their derivatives 2-ethoxy-4,6-
diphenyl-4H-pyran-3-carboxylic acid ethyl ester (2a), 4-(4-hydroxy-phenyl)-7,7-dimethyl-2-phenyl-
4,6,7,8-tetrahydro-chromen-5-one (2b) and 7-(4-amino-phenyl)-5-phenyl-1,5-dihydropyrano[2,3-
d]pyrimidine-2,4-dione (2c ) have been synthesized following both conventional and microwave
irradiation methods. The structures of the isolated compounds were elucidated on the basis of
UV-visible, FTIR, 1H NMR spectral data. The antimicrobial results showed some remarkable facts
about the structure–activity relationship, which states that the electronic atmosphere around the chalcone
derivative moieties and substituents considerably affect the antimicrobial potential of the synthesized
compounds. Theoretical calculation as well as antimicrobial activity of the compounds were also
studied.
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