Exploring substituents and solvent effects on the reduction potential and molecular properties of five derivatives of hydroxybenzophenone (HBP) with their possible conformations and isomers

Adeniyi, Adebayo A.; Conradie, Jeanet

doi:10.1007/s11224-020-01685-8

Cited by 4 publications

(1 citation statement)

References 35 publications

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“…[44,[94][95][96][97][98][99][100][101][102][103] Molecules with a higher, more positive reduction potentials (i. e., more favorable reduction) typically have lower-energy LUMOs (easier to accept an electron or differently stated, has a higher electron affinity) calculated by DFT. Reduction data obtained under the same experimental conditions as obtained for (1) and ( 2) are available for a series of βdiketones (ACN as solvent [69,70] ) and a series of 2-hydroxyphe-nones (DMSO as solvent [85,104,105] ), see data in Table 2. Given the similarity between the structures of ( 1) and (2) to β-diketones and 2-hydroxyphenones (Scheme 1), the reduction data of ( 1) and ( 2) can be compared to that of β-diketones and 2hydroxyphenones.…”

Section: Dftmentioning

confidence: 99%

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

Izuchukwu Ugwu,

Conradie

2024

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The growing interest in synthesizing electrochemically active organic ligands stems from extensive reports highlighting the applications of redox‐active organic molecules. These molecules play a crucial role in capturing and converting CO2 into valuable organic compounds, including carbonates used as solvents in lithium batteries. In this study, we present an electrochemical investigation of two chalcone derivatives, referred to as (1) and (2). We explored the influence of different solvent systems, specifically acetonitrile and dimethyl sulfoxide, on the reduction potential of these chalcones. The reported chalcone derivatives were characterized using various analytical techniques, including UV/Visible spectroscopy, Fourier Transform Infrared spectroscopy, Proton and Carbon‐13 nuclear magnetic resonance, as well as mass spectrometry. The characterization of the reported chalcones, exhibiting properties of both β‐diketones and 2‐hydroxyphenones, is underscored by a density functional theory (DFT) study of chalcones (1) and (2). This research establishes a correlation between the energies calculated through DFT and the experimental reduction potentials of chalcones (1) and (2), in comparing them with a series of β‐diketones and 2‐hydroxyphenones.

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Section: Dftmentioning

confidence: 99%

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

Izuchukwu Ugwu,

Conradie

2024

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Electrochemical behaviour of 2-hydroxybenzophenones and related molecules

Chiyindiko

Langner

Conradie

2022

Results in Chemistry

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Theoretical Investigation of Excited-State Intramolecular Double-Proton Transfer Mechanism of Substituent Modified 1, 3-Bis (2-Pyridylimino)-4,7-Dihydroxyisoindole in Dichloromethane Solution

Liu

Yuan

Wang

et al. 2021

J. Comput. Biophys. Chem.

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In this paper, density functional theory (DFT) and time-dependent DFT (TDDFT) methods were used to investigate substituent effects and excited-state intramolecular double-proton transfer (ESIDPT) in 1, 3-bis (2-pyridylimino)-4, 7-dihydroxyisoindole (BPI–OH) and its derivatives. The results of a systematic study of the substituent effects of electron-withdrawing groups (F, Cl and Br) on the adjacent sites of the benzene ring were used to regulate the photophysical properties of the molecules and the dynamics of the proton-transfer process. Geometric structure comparisons and infrared (IR) spectroscopic analysis confirmed that strengthening of the intramolecular hydrogen bond in the first excited state (S1) facilitated proton transfer. Functional analysis of the reduced density gradient confirmed these conclusions. Double-proton transfer in BPI–OH is considered to occur in two steps, i.e., BPI–OH (N) [Formula: see text] BPI–OH (T1) [Formula: see text] BPI–OH (T2), in the ground state (S0) and the S1 state. The potential-energy curves (PECs) for two-step proton transfer were scanned for both the S0 and S1 states to clarify the mechanisms and pathways of proton transfer. The stepwise path in which two protons are consecutively transferred has a low energy barrier and is more rational and favorable. This study shows that the presence or absence of coordinating groups, and the type of coordinating group, affect the hydrogen-bond strength. A coordinating group enhances hydrogen-bond formation, i.e., it promotes excited-state intramolecular proton transfer (ESIPT).

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Exploring substituents and solvent effects on the reduction potential and molecular properties of five derivatives of hydroxybenzophenone (HBP) with their possible conformations and isomers

Cited by 4 publications

References 35 publications

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

Electrochemical behaviour of 2-hydroxybenzophenones and related molecules

Theoretical Investigation of Excited-State Intramolecular Double-Proton Transfer Mechanism of Substituent Modified 1, 3-Bis (2-Pyridylimino)-4,7-Dihydroxyisoindole in Dichloromethane Solution

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