Abstract
The α-H acidity is an important chemical property of ketones that has attracted much research interest. Theoretical prediction of pKa for ketone α-H is significant. In this work, we theoretically studied the nuclear shielding of various α-Hs in a set of ketones and that of the corresponding enolic hydroxyl Hs in tautomeric enol forms. It has been demonstrated through linear regression analyses that the pKa values of these ketones correlate with both sets of the calculated nuclear shielding values. The correlation coefficient R2 of the linear correlation relationship is 0.90. The present work has provided a new approach to computationally evaluating the acidity of α-Hs in ketones, enabling us to semi-empirically predict the ketone α-H acidity from the calculated nuclear shielding values. [Figure not available: see fulltext.].
Original language | English |
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Article number | 354 |
Journal | Journal of Molecular Modeling |
Volume | 25 |
Issue number | 12 |
DOIs | |
State | Published - Dec 1 2019 |
Bibliographical note
Publisher Copyright:© 2019, Springer-Verlag GmbH Germany, part of Springer Nature.
Keywords
- Enol
- Ketone
- Linear correlation
- Nuclear shielding
- pK
ASJC Scopus subject areas
- Catalysis
- Inorganic Chemistry
- Computer Science Applications
- Physical and Theoretical Chemistry
- Computational Theory and Mathematics
- Organic Chemistry