Correlation between the pK a and nuclear shielding of α-hydrogen of ketones

Suting Xing; Juanfeng Lu; Xinyun Zhao; Xi Chen; Chang Guo Zhan

doi:10.1007/s00894-019-4244-8

Correlation between the pK _a and nuclear shielding of α-hydrogen of ketones

Suting Xing, Juanfeng Lu, Xinyun Zhao, Xi Chen, Chang Guo Zhan

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

The α-H acidity is an important chemical property of ketones that has attracted much research interest. Theoretical prediction of pK_a 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 pK_a 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
Article number	354
Journal	Journal of Molecular Modeling
Volume	25
Issue number	12
DOIs	https://doi.org/10.1007/s00894-019-4244-8
State	Published - Dec 1 2019

Bibliographical note

Publisher Copyright:
© 2019, Springer-Verlag GmbH Germany, part of Springer Nature.

Funding

The work was supported by the National Natural Science Foundation of China (grant number 21273089), the Fundamental Research Funds for the South-Central University for Nationalities (CZW17004), the Open Project Fund of the Key Laboratory of the Pesticides and Chemical Biology of Central China Normal University (grant number 2018-A01).

Funders	Funder number
Open Project Fund of the Key Laboratory of the
Pesticides and Chemical Biology of Central China Normal University
National Natural Science Foundation of China (NSFC)	21273089
South-Central University for Nationalities	CZW17004
Fundamental Research Funds for Central Universities of the Central South University	2018-A01

Keywords

Enol
Ketone
Linear correlation
Nuclear shielding
pK

ASJC Scopus subject areas

Catalysis
Computer Science Applications
Physical and Theoretical Chemistry
Organic Chemistry
Computational Theory and Mathematics
Inorganic Chemistry

Access to Document

10.1007/s00894-019-4244-8

Cite this

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title = "Correlation between the pK a and nuclear shielding of α-hydrogen of ketones",

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.].",

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AU - Xing, Suting

AU - Lu, Juanfeng

AU - Zhao, Xinyun

AU - Chen, Xi

AU - Zhan, Chang Guo

PY - 2019/12/1

Y1 - 2019/12/1

N2 - 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.].

AB - 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.].

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