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.
Original language | English |
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Pages (from-to) | 3414-3421 |
Number of pages | 8 |
Journal | Chemistry : A European Journal |
Volume | 22 |
Issue number | 10 |
Early online date | 28 Jan 2016 |
DOIs | |
Publication status | Published - 1 Mar 2016 |
Bibliographical note
. © 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 detailsKeywords
- aggregation
- betaines
- bond energy
- hydrogen bonds
- nitrogen heterocycles
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Structure of Amido Pyridinium Betaines: Persistent Intermolecular C-H•••N Hydrogen Bonding in Solution
Douthwaite, R. E. (Creator) & Slattery, J. M. (Contributor), University of York, 15 Mar 2016
DOI: 10.15124/baf68c5b-7daa-49f9-afe9-024eaba18694
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