Neutron Diffraction Study of Significant sp3 and sp2 C–H Bond Shortening in a Fluorinated Pyridinium Saccharinate
- 30 March 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 143 (14), 5550-5557
- https://doi.org/10.1021/jacs.1c02570
Abstract
We have experimentally shown by neutron diffraction significant shortening of both sp3- and sp2-hybridized C–H bonds to 1.092(2) and 1.081(1) Å in a hydrogen-bonded crystal of a difluorinated compound, 4-((2,2-difluoroethoxy)methyl)pyridinium saccharinate. Both MP2 and DFT calculations affirmed the C–H bond shrinkages. Sanderson’s electronegativity equalization principle provides insight into the shortening of the C–H covalent bond lengths for both sp3- and sp2-hybridized carbon atoms. To the best of our knowledge, this neutron diffraction study has revealed the largest extents of sp3 and sp2 C–H bond shrinkages with a 3-sigma rule being satisfied.Funding Information
- National Synchrotron Radiation Research Center (N-2018-R-017)
- U.S. Department of Energy (DE-AC05-00OR22725)
- Ministry of Science and Technology, Taiwan (MOST 106-2113-M-027-001)
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