Redefining interactions: The concept of the resonance-impaired hydrogen bond (RIHB) as an interaction in which a conjugated π system strongly impairs the formation of a hydrogen bond (HB) is introduced. A typical HB involving charged species can have a formation energy of tens of kcal mol , whereas the corresponding value for the examined RIHB is only 2.6 kcal mol . Quantum chemical topology tools are used to analyse the low formation energy of the studied RIHBs.

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