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- Title
Relative pK<sub>a</sub> of some anilinium derivatives in methanol, acetonitrile, and tetrahydrofurane solvents.
- Authors
Ghalami‐Choobar, Bahram; Ghiami‐Shomami, Ali; Fereidoonzadeh, Masoomeh
- Abstract
In this study, the relative pKa values of nine anilinium derivatives in methanol (MeOH), acetonitrile (AN), and tetrahydrofurane (THF) solutions were successfully calculated with mean absolute deviations of 0.63, 0.68, and 0.75 pKa units, respectively. To this aim, their gas‐phase basicities were computed using the CBS‐QB3 composite method. Also, conductor‐like polarizable continuum model (CPCM) with UAHF, UAKS and UA0 cavities and SM8 solvation models at HF/6‐31+G(d) level of theory were applied for the calculation of the solvation Gibbs free energies. The obtained results indicate that there is reliable correlation between the experimental and computed pKa values in the studied solutions. Therefore, to extend the pKa database for anilines, correlation equations were used to predict the pKa values in the investigated solvents. The ability to predict the acidities and basicities in gas and liquid phases through reliable computational approaches breaks the limitations of experimental techniques. Therefore, the gas‐phase basicities and relative pKa values of some anilines in methanol (MeOH), acetonitrile (AN), and tetrahydrofurane (THF) solvents are computed. Then, reliable computational methods and their corresponding correlation equations are applied to extend the acidity databank for anilines.
- Subjects
ANILINE derivatives; METHANOL; ACETONITRILE; AQUEOUS solutions; GAS phase reactions
- Publication
Journal of the Chinese Chemical Society, 2019, Vol 66, Issue 2, p150
- ISSN
0009-4536
- Publication type
Article
- DOI
10.1002/jccs.201800139