Abstract
The solid-state structures of three H-bonded enol forms of 5-substituted 9-hydroxyphenalenones were investigated to accurately determine the H atom positions of the intramolecular hydrogen bond. For this purpose, single-crystal X-ray diffraction (SC-XRD) data were evaluated by invariom-model refinement. In addition, QM/MM computations of central molecules in their crystal environment show that results of an earlier standard independent atom model refinement, which pointed to the presence of a resonance-assisted hydrogen bond in unsubstituted 9-hydroxyphenalone, are misleading: in all our three and the earlier solid-state structures the lowest energy form is that of an asymmetric hydrogen bond (CS form). Apparent differences of results from SC-XRD and other analytical methods are explained.
Funding source: DFG
Award Identifier / Grant number: DI 921/6-1
Acknowledgments
We thank the DFG, project DI 921/6-1, for financial support.
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: B.D. acknowledges funding from the Deutsche Forschungsgemeinschaft DFG, project DI 921/6-1.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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