Conformation analysis of a novel fluorinated chalcone

Abstract

Chalcones are an important class of natural compounds that exhibit numerous biological activities. In this paper, we report the synthesis and characterization of new fluorinated chalcone (FCH). The molecular geometry was determined by means of single crystal X-ray diffraction, and density functional theory (DFT) at B3LYP, M06-2X functionals and MP2 method, with the 6-311++G(d,p) basis set, was applied to optimize the ground state geometry and to study the molecular conformational stability. The molecular electrostatic potential (MEP) was also investigated at the same level of theory in order to identify and quantify the possible reactive sites. The FCH crystallizes in the centrossymmetric space group [Formula: see text] with two independent conformers (α and β) in the asymmetric unit cell. The α conformer is arranged in planar layer whereas the β creates a layer of non-classical dimer along c axis, that differ from α in about 11° in the orientation of phenyl groups. The stabilization of the β conformer is achieved by C-H···π arrangement. The small energy difference between the conformers (0.086 kcal mol) and the absence of activation energy indicates that the conversion between them can takes place at room temperature and the β isomer is stable only in solid state. The FCH most electrophilic site occurs on the oxygen atom from the carboxyl group with absolute MEP value of about -52 kcal mol whereas the MEP value calculated for F site is about -23 kcal mol.

A Structure-Guided Designed Small Molecule Is an Anticancer Agent and Inhibits the Apoptosis-Related MCL-1 Protein

“…The greater the gap, the less reactive the molecule is [55]. Compared with other chalcones and their derivatives [56,57], MNC has high gap energy, with E GAP = 5.922 eV. Finally, the MEP map calculated for MNC is presented in Figure 6c and shows the energy in different molecular sites as a color-based scale ranging from δ = −1.9862 eV to δ = +1.9862 eV.…”

Materiais Cristalinos Funcionais e Desenvolvimento Tecnológico

“…Um exemplo de compostos cristalinos aplicados a soluções voltadas ao meio ambiente que tem chamado atenção no meio científico, e que também tem sido objeto de estudo 22,[26][27][28][29][30] por parte do grupo de química teórica e estrutural de Anápolis (QTEA) são as chalconas. Quimicamente esses são compostos orgânicos que pertencem à família dos flavonóides, sendo abundantes na natureza e de fácil síntese em laboratório.…”

Structure and Physical Properties of Cardamonin: A Spectroscopic and Computational Approach

“…Structurally, chalcones possess a common chemical 1,3-diaryl-2-propen-1-one scaffold in which the two aryl groups are linked together by carbonyl and an α,β-unsaturated system [ 4 , 5 ]. In recent years, chalcones have also been applied using a technological approach such as a nonlinear optic (NLO) material [ 6 , 7 ]. Cardamonin (2′,4′-dihydroxy-6′-methoxychalcone, C 16 H 14 O 4 ) belongs to the chemical class of chalcones which are phenolic compounds isolated from several species of Zingiberaceae including Alpinia katsumadai, Alpinia conchigera, Alpinia rafflesiana, Amomum subulatum and Boesenbergia pandurata [ 8 ].…”