NDLI: Conformation analysis of a novel fluorinated chalcone

Content Provider	Springer Nature Link
Author	Carvalho, Paulo S. Custodio, Jean M. F. Vaz, Wesley F. Cirilo, Cassio C. Cidade, Amanda F. Aqui, Gilberto L. B. Campos, Dulcinea M. B. Cravo, Pedro Coelho, Clarimar J. Oliveira, Solemar S. Camargo, Ademir J. Napolita, Hamilton B.
Copyright Year	2017
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 $$ P\overline{1} $$ 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−1) 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−1 whereas the MEP value calculated for F site is about −23 kcal mol−1.
Starting Page	1
Ending Page	11
Page Count	11
File Format	PDF
ISSN	16102940
Journal	Journal of Molecular Modeling
Volume Number	23
Issue Number	3
e-ISSN	09485023
Language	English
Publisher	Springer Berlin Heidelberg
Publisher Date	2017-03-01
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	DFT Fluorinated chalcone X-ray diffraction Computer Applications in Chemistry Molecular Medicine Computer Application in Life Sciences Characterization and Evaluation of Materials Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Physical and Theoretical Chemistry Computational Theory and Mathematics Catalysis Inorganic Chemistry Computer Science Applications

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