Malaspina, Lorraine A.; White, Allan H.; Wege, Dieter; Tolmie, Michael B.; Skelton, Brian W.; Grabowsky, Simon (2017). Tautomerism in acyl-pyrazolones and in a novel photolysis product—importance and impact of the accurate localization of hydrogen atoms in crystal structures. Structural chemistry, 28(5), pp. 1343-1357. Springer 10.1007/s11224-017-1005-0
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Acyl-pyrazolones exist in four different tautomeric forms (two keto and two enol) in crystal structures. Routine crystal structure refinements using an independent atom model and routine isolated-molecule calculations fail in locating the mobile hydrogen atoms accurately in 22 investigated acyl-pyrazolone examples. However, a combination of both within the framework of quantum crystallography represented by the method of Hirshfeld atom refinement accurately locates the mobile hydrogen atom in a resonance-assisted hydrogen bond of title compound 3, a novel photolysis product. The impact of the hydrogen atom position on the resonance system of the non-hydrogen framework of the various tautomers is discussed, and the importance of intermolecular interactions for the positioning of the hydrogen atom is highlighted.
Item Type: |
Journal Article (Original Article) |
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Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Malaspina, Lorraine, Grabowsky, Simon |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
1040-0400 |
Publisher: |
Springer |
Language: |
English |
Submitter: |
Simon Grabowsky |
Date Deposited: |
06 Feb 2020 11:56 |
Last Modified: |
05 Dec 2022 15:35 |
Publisher DOI: |
10.1007/s11224-017-1005-0 |
BORIS DOI: |
10.7892/boris.138430 |
URI: |
https://boris.unibe.ch/id/eprint/138430 |
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