The acid dissociation constants and 1H NMR chemical shieldings of organic compounds are important properties that have attracted much research interest. However, few studies have explored the relationship between these two properties. In this work, we theoretically studied the NMR chemical shifts of a series of carboxylic acids and amines in the gas phase and in aqueous solution. It was found that the negative logarithms of the experimental acid dissociation constants (i.e., the pKa values) of the organic acids and amines in aqueous solution correlate almost linearly with the corresponding calculated NMR chemical shieldings. Key factors that affect the theoretically predicted pKa values are discussed in this paper. The present work provides a new way to predict the pKa values of organic/biochemical compounds. [Figure not available: see fulltext.]
|Journal||Journal of Molecular Modeling|
|State||Published - Jul 1 2018|
Bibliographical noteFunding Information:
Acknowledgements This research was supported in part by the National Natural Science Foundation of China (grant no. 21273089) and the Special Fund for Basic Scientific Research of Central Colleges, South-Central University for Nationalities (CZY14004).
© 2018, Springer-Verlag GmbH Germany, part of Springer Nature.
- H NMR chemical shieldings
- Linear correlation
- Organic acid
ASJC Scopus subject areas
- Computer Science Applications
- Physical and Theoretical Chemistry
- Organic Chemistry
- Computational Theory and Mathematics
- Inorganic Chemistry