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Hydrogen‐Bond Weakening through π Systems: Resonance‐Impaired Hydrogen Bonds (RIHB)
Author(s) -
GuevaraVela José Manuel,
RomeroMontalvo Eduardo,
del RíoLima Alejandra,
Martín Pendás Ángel,
HernándezRodríguez Marcos,
Rocha Rinza Tomás
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703436
Subject(s) - hydrogen bond , conjugated system , resonance (particle physics) , hydrogen , value (mathematics) , service (business) , electron paramagnetic resonance , computer science , chemistry , materials science , chemical physics , computational chemistry , nanotechnology , crystallography , physics , atomic physics , quantum mechanics , molecule , organic chemistry , business , polymer , marketing , machine learning
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 (see figure). Quantum chemical topology tools are used to analyse the low formation energy of the studied RIHBs.