The Influence of Methoxy and Ethoxy Groups on Supramolecular Arrangement of Two Methoxy-chalcones

Abstract

The structures of two methoxylated chalcones, namely (E)-1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and (E)-3-(4-ethoxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one, reveal the effect of the inclusion of the methoxyl and ethoxyl substituents of the conformation on methoxy-chalcone. Structural comparative study between two chalcones was done in this work and some effects on geometric parameters, such as planarity and dihedral angles, were described. In addition, intermolecular interactions responsible for crystalline packaging were investigated by Hirshfeld surfaces and the values of those interactions were analysed by comparing experimental and theoretical models. The molecular stability was expressed in terms of softness and hardness, both obtained from frontier molecular orbitals. Finally, there is a good agreement between calculated and experimental infrared spectrum, which allowed the assignment of the normal vibrational modes.

Two-Photon Absorption and Multiphoton Excited Fluorescence of Acetamide-Chalcone Derivatives: The Role of Dimethylamine Group on the Nonlinear Optical and Photophysical Properties

“…The high values of ε(λ) suggested that such a band could be ascribed to strongly allow π-π* electronic transitions. It should be highlighted that except for ChN(CH3)2, ChOCH3 and ChOCH2CH3 presented the most red-shift effects, indicating that these groups may be affecting their molecular planarity [ 24 ] and hence increasing the effective conjugation length, leading to a decrease in the energy of the electronic transition. In addition, the red-shift observed for these compounds could be associated with the non-bonding electrons of methoxy and ethoxy groups [ 25 , 26 ].…”

Arylsulfonamide chalcones as alternatives for fuel additives: antioxidant activity and machine learning protocol studies

“…Small differences, such as the position of a substituent or different substituents in the same position, can corroborate different conformations of the molecule, different interactions, and supramolecular arrangements. 104–108…”

The reaction of (2-oxo-2-phenyl-ethyl sulfanyl)-Acetic Acid with Chalcones: Double Michael Addition-Aldol Reaction Formation of Unexpected (5-Benzoyl-2-hydroxy-2,4-6-triphenyl-cyclohexyl) -phenyl-methanone

“…Claisen Schmidt condensation, in which aromatic aldehydes and acetophenones are condensed, is the typical method for producing chalcones [17][18][19] . Two aromatic rings are present in this compound class, joined by a three-carbon bridge, along with a keto carbonyl group and one, α, β-unsaturation 20 .…”