Conformational preferences in a series of α-hydroxy ketone derivatives: interplay of conformational energies and lattice cohesive energies

Insan, Sandeep; Sudheendranath, Athul; Venugoplan, P.; Kumar, Anil; Thomas, Sajesh P.

doi:10.1039/d2ce00700b

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“…Recently we reported the conformational preferences and the trends in lattice cohesive energies for a series of α-hydroxyketones and the counterbalance of intra- and intermolecular interactions in their crystal structures . In this work, we investigate the contribution of organic fluorine to the crystal packing as well as molecular conformation in a series of α-fluoroketones which are analogous to those structureswith the hydroxyl group substituted by a F atom (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Fluorine versus Hydroxyl in Supramolecular Space: Effect of Organic Fluorine in Molecular Conformation, Lattice Cohesive Energies, and Receptor Binding in a Series of α-Fluoroketones

Sudheendranath

Sandeep

Avinash

et al. 2023

Crystal Growth & Design

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We examine the effect of organic fluorine in the molecular conformation and supramolecular packing in a series of α-fluoroketones in comparison to the analogous α-hydroxyketones. Crystal structures of a series of seven α-fluoroketone analogues have been analyzed using single-crystal XRD, and their crystal-packing features have been investigated using a variety of computational tools. Analysis of molecular conformations in this series of αfluoroketone structures, along with conformational energy scans, revealed a preference for a near-antiperiplanar conformation for α-fluoroketones as opposed to a syn conformation in their α-hydroxy analogues. A quantitative analysis of intermolecular interaction motifs such as C−Hetc. in terms of interaction energies and electron density topological parameters from a QTAIM (quantum theory of atoms in molecules) approach reveal their relative strengths and distance dependence. Electron localization function (ELF) and deformation density maps bring out the electrostatic nature of weak interactions involving organic fluorine. Lattice energy values estimated using the CE-B3LYP method show dominant contributions from dispersion in all these structures, which are around 3−4-fold higher than the electrostatic contribution. While the lattice energy values of the α-fluoroketones are found to be lower than those of their hydroxy analogues, a molecular docking study with a common protein receptor site reveals comparable docking scores for αfluoroketones with respect to the analogous α-hydroxyketones.

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Section: Introductionmentioning

confidence: 99%

Fluorine versus Hydroxyl in Supramolecular Space: Effect of Organic Fluorine in Molecular Conformation, Lattice Cohesive Energies, and Receptor Binding in a Series of α-Fluoroketones

Sudheendranath

Sandeep

Avinash

et al. 2023

Crystal Growth & Design

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Conformational preferences in a series of α-hydroxy ketone derivatives: interplay of conformational energies and lattice cohesive energies

Abstract: Crystal structures of a series of six α-hydroxy ketone derivatives have been analysed in the context of their molecular conformational preferences. The crystal structures obtained by single crystal X-ray diffraction...

Cited by 1 publication

References 59 publications

Fluorine versus Hydroxyl in Supramolecular Space: Effect of Organic Fluorine in Molecular Conformation, Lattice Cohesive Energies, and Receptor Binding in a Series of α-Fluoroketones

Fluorine versus Hydroxyl in Supramolecular Space: Effect of Organic Fluorine in Molecular Conformation, Lattice Cohesive Energies, and Receptor Binding in a Series of α-Fluoroketones

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