4.4 Article

Correlation between the pKa and nuclear shielding of α-hydrogen of ketones

Journal

JOURNAL OF MOLECULAR MODELING
Volume 25, Issue 12, Pages -

Publisher

SPRINGER
DOI: 10.1007/s00894-019-4244-8

Keywords

Nuclear shielding; pK(a); Ketone; Enol; Linear correlation

Funding

  1. National Natural Science Foundation of China [21273089]
  2. Fundamental Research Funds for the South-Central University for Nationalities [CZW17004]
  3. Open Project Fund of the Key Laboratory of the Pesticides and Chemical Biology of Central China Normal University [2018-A01]

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The alpha-H acidity is an important chemical property of ketones that has attracted much research interest. Theoretical prediction of pK(a) for ketone alpha-H is significant. In this work, we theoretically studied the nuclear shielding of various alpha-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 pK(a) values of these ketones correlate with both sets of the calculated nuclear shielding values. The correlation coefficient R-2 of the linear correlation relationship is 0.90. The present work has provided a new approach to computationally evaluating the acidity of alpha-Hs in ketones, enabling us to semi-empirically predict the ketone alpha-H acidity from the calculated nuclear shielding values.

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