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- Publisher
- Springer Journals
- Copyright
- Copyright © 2018 by Springer-Verlag GmbH Germany, part of Springer Nature
- Subject
- Chemistry; Computer Applications in Chemistry; Molecular Medicine; Computer Appl. in Life Sciences; Characterization and Evaluation of Materials; Theoretical and Computational Chemistry
- ISSN
- 1610-2940
- eISSN
- 0948-5023
- DOI
- 10.1007/s00894-018-3690-z
- pmid
- 29858663
- Publisher site
- See Article on Publisher Site
Abstract
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 pK a 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 pK a values are discussed in this paper. The present work provides a new way to predict the pK a values of organic/biochemical compounds.
Journal
Journal of Molecular Modeling – Springer Journals
Published: Jun 1, 2018