Conformational equilibrium and intramolecular hydrogen bond of 4′X and 4X substituted 2′(OH)chalcones

Devia, A.; Ferretti, F.H.; Ponce, Carlos; Tomás, F.

doi:10.1016/s0166-1280(99)00239-0

Cited by 17 publications

(10 citation statements)

References 29 publications

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“…93%, 566 out of 607). All N/O meta-substituted chalcones (59) are in this range for such a torsion angle. The torsion angles of molecules A and B of 2 fall into this range of values, while molecule C deviated from this trend and is the first to be reported for a N/O meta-substituted chalcone with a C1-C7-C8-C9 torsion angle measuring close 0°.…”

Section: Conformational Analysis Ofmentioning

confidence: 93%

Polymorphism and conformerism in chalcones

et al. 2016

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Herein two solid state phenomena have been observed in two chalcones. Firstly, polymorphism has been found in (E)-1-(2-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (1). This compound crystallizes with only one conformer rather than three in the known reported structure. In the polymorphs, the conformation of the phenyl ring bonded to carbonyl differs slightly. The intermolecular hydrogen bonding from NH 2 is the main interaction responsible for polymorphism. Our polymorph is assembled only with weak N-H⋯π interactions instead of strong N-H⋯O and N-H⋯N ones observed in the known structure.DFT calculations reveal that the three conformers of the known polymorph deviate from the minimum energy conformation which is adopted in our crystal form to compensate for the absence of strong intermolecular contacts. Second, conformerism is reported for (E)-1-(3-hydroxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (2). Three crystallographically independent molecules are found in the structure of 2: two of them are similarly planar with an anti conformation around the single bond between the carbonyl and α carbons while the third one is twisted, with its phenyl ring bonded to carbonyl rotated by ca. 60°besides presenting a syn conformation around the corresponding rotatable bond. Both conformational features are related to the crystal packing, allowing accommodation of twisted molecules onto the layers made up of hydrogen bonded planar molecules. Furthermore, our potential energy surface scans indicate that the planar and twisted conformations of the phenyl ring bonded to carbonyl are not compatible with the syn and anti conformations of the chalcone skeleton.

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Section: Conformational Analysis Ofmentioning

confidence: 93%

Polymorphism and conformerism in chalcones

et al. 2016

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“…In these materials, the C O bond acts as an electron-withdrawing group, and electron-rich substituents in the aromatic rings serve as electron-donating groups, forming a so-called D-Á Á ÁA type molecule. When the electron-rich groups are located on the 4 and/or 4 0 positions, the electron flow follows a Ã-shaped path, and therefore the molecule is called a Ã-shaped molecule (Devia et al, 1999).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures of three 1-[4-(4-bromobutoxy)phenyl] chalcone derivatives: (E)-1-[4-(4-bromobutoxy)phenyl]-3-phenylprop-2-en-1-one, (E)-1-[4-(4-bromobutoxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one and (E)-1-[4-(4-bromobutoxy)phenyl]-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

Maragatham¹,

Selvarani²,

Rajakumar³

et al. 2017

Acta Cryst E

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“…In these materials, the C O bond acts as the electronwithdrawing group, and electron-rich substituents in the aromatic rings serve as electron-donating groups, forming a so-called DÐ%Á Á ÁA-type molecule. When the electron-rich groups are located on the 4 and/or 4 H positions, the electron ow follows a Ã-shaped path, and therefore the molecule is called a Ã-shaped molecule (Devia et al, 1999). During our search for chalcone non-linear optical materials, the title compound, (I), was synthesized.…”

Section: Commentmentioning

confidence: 99%

1-(4-Bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one

Wang¹,

Zhang²,

Lu³

et al. 2004

Acta Crystallogr C

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In the molecule of the title compound, C16H13BrO, the two benzene rings are rotated in opposite directions with respect to the central C-C=C-C part of the molecule. The phenone O atom deviates from the least-squares plane of the molecule by 0.300 (3) A. In the crystal structure, molecules are paired through C-H...pi interactions. The molecular pairs along [001] are hydrogen bonded through three translation-related co-operative hydrogen bonds in the 'bay area', forming molecular chains, which are further hydrogen bonded through C-H...Br weak interactions, forming (010) molecular layers. In the third direction, there are only weak van der Waals interactions. The co-operative hydrogen bonds in the 'bay area' are discussed briefly.

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Conformational equilibrium and intramolecular hydrogen bond of 4′X and 4X substituted 2′(OH)chalcones

Cited by 17 publications

References 29 publications

Polymorphism and conformerism in chalcones

Polymorphism and conformerism in chalcones

Crystal structures of three 1-[4-(4-bromobutoxy)phenyl] chalcone derivatives: (E)-1-[4-(4-bromobutoxy)phenyl]-3-phenylprop-2-en-1-one, (E)-1-[4-(4-bromobutoxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one and (E)-1-[4-(4-bromobutoxy)phenyl]-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

1-(4-Bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one

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