Quantitative assessment of reparameterized PM6 (rPM6) for hydrogen abstraction reactions

Saitô, Tôru; Kambara, Hiroki; Takano, Yu

doi:10.1080/00268976.2019.1700313

Cited by 5 publications

(3 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…However, these methods are labor intensive and require specialized equipment that is not commonly available in laboratories . Computational estimation of C–H BDE is comparatively fast and avoids the requirement for sophisticated instrumentation and related know-how. ,− …”

Section: Introductionmentioning

confidence: 99%

Theoretical and Experimental Investigation of Autoxidation Propensity of Selected Drugs in Solution State

et al. 2023

View full text Add to dashboard Cite

The C−H bond dissociation energy (BDE) of drug molecules is often used to estimate their relative propensities to undergo autoxidation. BDE calculations based on electronic structures provide a convenient means to estimate the risk for a given compound to degrade via autoxidation. This study aimed to verify the utility of calculated C−H BDEs of a range of drug molecules in predicting their autoxidation propensities, in the solution state. For the autoxidation study, 2,2′-azobis (2methylpropionitrile) was employed as the solution state stressor, and the experimental reaction rate constants were determined employing ultraperformance liquid chromatographic (UPLC) methods. Reaction rates in the solution state were compared to the calculated C−H BDE values of the respective compounds. The results indicated a poor correlation for compounds in the solution state, and their relative stabilities could not be explained with C−H BDE. On the other hand, a favorable relationship was observed between the relative extent of ionization and the autoxidation rates of the selected compounds. In the solution state, factors such as the type and extent of drug ionization, degree and type of solvation have been shown to contribute to differences in reactivity. By applying the computational method involving the effect of H-atom abstraction and potential ionization sites in the molecule, the calculated C−H BDE should relate better to the experimental autoxidation rates.

show abstract

Section: Introductionmentioning

confidence: 99%

Theoretical and Experimental Investigation of Autoxidation Propensity of Selected Drugs in Solution State

et al. 2023

View full text Add to dashboard Cite

show abstract

“…У випадку хімічних частинок PhMe 2 CH + , утворюваних внаслідок відриву електрона, та PhMe 2 C + , утворюваних внаслідок відриву гідрид-іона, при обчисленнях зберігалась оптимізована геометрія вихідної молекули -кумолу. Застосування методу РМ7 для оцінки ентальпії реакцій відриву Н-атома О-атомом металвмісної хімічної частинки проаналізовано у праці [22].…”

Section: методи обчислення термохімічних величинunclassified

On the limiting stage of oxidation of alkylarenes by potassium permanganate

Opeida¹,

Volkova²

2022

Visnyk Lviv Univ. Ser. Chem.

View full text Add to dashboard Cite

“…As such, the reported BSEs are not comparable to experimental BDEs, but they serve as an ideal resource for developing and evaluating lower-cost computational chemistry methods used for a wide range of applications in chemistry and biology. Similar datasets to the one proposed in this work are available in the literature, but they tend to be small in terms of the total number of datapoints 25 , lack bond-type diversity 26 , 27 or are calculated using less accurate computational chemistry methods compared to the one used in this work 28 – 30 . To the best of our knowledge, an accurate and extensive dataset of computationally predicted BSEs is not available in the literature.…”

Section: Background and Summarymentioning

confidence: 99%

BSE49, a diverse, high-quality benchmark dataset of separation energies of chemical bonds

et al. 2021

View full text Add to dashboard Cite

We present an extensive and diverse dataset of bond separation energies associated with the homolytic cleavage of covalently bonded molecules (A-B) into their corresponding radical fragments (A. and B.). Our dataset contains two different classifications of model structures referred to as “Existing” (molecules with associated experimental data) and “Hypothetical” (molecules with no associated experimental data). In total, the dataset consists of 4502 datapoints (1969 datapoints from the Existing and 2533 datapoints from the Hypothetical classes). The dataset covers 49 unique X-Y type single bonds (except H-H, H-F, and H-Cl), where X and Y are H, B, C, N, O, F, Si, P, S, and Cl atoms. All the reference data was calculated at the (RO)CBS-QB3 level of theory. The reference bond separation energies are non-relativistic ground-state energy differences and contain no zero-point energy corrections. This new dataset of bond separation energies (BSE49) is presented as a high-quality reference dataset for assessing and developing computational chemistry methods.

show abstract

Quantitative assessment of reparameterized PM6 (rPM6) for hydrogen abstraction reactions

Cited by 5 publications

References 30 publications

Theoretical and Experimental Investigation of Autoxidation Propensity of Selected Drugs in Solution State

Theoretical and Experimental Investigation of Autoxidation Propensity of Selected Drugs in Solution State

On the limiting stage of oxidation of alkylarenes by potassium permanganate

BSE49, a diverse, high-quality benchmark dataset of separation energies of chemical bonds

Contact Info

Product

Resources

About