Hydrogen Bonding

Right in the middle

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Science  15 Mar 2019:
Vol. 363, Issue 6432, pp. 1188-1189
DOI: 10.1126/science.363.6432.1188-f

Hydrogen bonding is a deceptively subtle concept. Typically, there is a donor with a strong covalent bond to hydrogen and an acceptor that attracts the hydrogen much more weakly. But what if the donor and acceptor are equivalent? Is equal sharing possible? Perrin and Wu explored this question in the intramolecular hydrogen bonds of keto-enol tautomers by nuclear magnetic resonance spectroscopy of oxygen-18 isotopologues. Whereas hydrogen typically seems to oscillate in its affinity for competing sites, nitromalonamide trapped it right in between both oxygens.

J. Am. Chem. Soc. 141, 4103 (2019).

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