Hydrogen-Bond Weakening through π Systems: Resonance-Impaired Hydrogen Bonds (RIHB).
José Manuel Guevara-VelaEduardo Romero-MontalvoAlejandra Del Río-LimaAngel Martin PendásMarcos Hernández-RodríguezTomás Rocha-RinzaPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2017)
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-1 , whereas the corresponding value for the examined RIHB is only 2.6 kcal mol-1 . Quantum chemical topology tools are used to analyse the low formation energy of the studied RIHBs.