Thatcher, Robert James, Johnson, David Grahame, Slattery, John Martin orcid.org/0000-0001-6491-8302 et al. (1 more author) (2016) Structure of Amido-Pyridinium Betaines:Persistent Intermolecular C-H•••N Hydrogen Bonding in Solution. Chemistry : A European Journal. pp. 3414-3421. ISSN 1521-3765
Abstract
A hydrogen bond of the type C-H⋯X (X=O or N) is known to influence the structure and function of chemical and biological systems in solution. C-H⋯O hydrogen bonding in solution has been extensively studied, both experimentally and computationally, whereas the equivalent thermodynamic parameters have not been enumerated experimentally for C-H⋯N hydrogen bonds. This is, in part, due to the lack of systems that exhibit persistent C-H⋯N hydrogen bonds in solution. Herein, a class of molecule based on a biologically active norharman motif that exhibits unsupported intermolecular C-H⋯N hydrogen bonds in solution has been described. A pairwise interaction leads to dimerisation to give bond strengths of about 7 kJ mol-1 per hydrogen bond, which is similar to chemically and biologically relevant C-H⋯O hydrogen bonding. The experimental data is supported by computational work, which provides additional insight into the hydrogen bonding by consideration of electrostatic and orbital interactions and allowed a comparison between calculated and extrapolated NMR chemical shifts.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | . © 2016, Wiley-VCH. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details |
Keywords: | aggregation,betaines,bond energy,hydrogen bonds,nitrogen heterocycles |
Dates: |
|
Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 17 Feb 2016 16:34 |
Last Modified: | 21 Dec 2024 00:10 |
Published Version: | https://doi.org/10.1002/chem.201503884 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/chem.201503884 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:95247 |
Downloads
Filename: Betaine_paper_PURE.docx
Description: Betaine paper PURE
Filename: Betaine_paper_PURE_SI.docx
Description: Betaine paper PURE SI