Oxane oxide: a tautomer of hydrogen peroxide.

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If H3N+-O is viable compared with its tautomer H2N-OH when carrying water bridges, then why not try H2O+-O vs HO-OH?

There are no examples to be found in crystal structures! The solvated structure of H2O+-O is modified directly from that of H3N+-Oand the computed (ωB97XD/6-311++G(d,p)/SCRF=water) structure[1] is shown below. Noteworthy is that the hydrogen bonds at the O+ end are far stronger than those to at the O end.


The corresponding hydrated hydrogen peroxide is 16.3 kcal/mol lower in free energy; this compares favourably with the value for water itself and suggests that oxane oxide might also be capable of isolation inside a suitable hydrogen bond stabilising cavity.


  1. Henry S Rzepa., "H20O11", 2016. http://dx.doi.org/10.14469/ch/192005

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