Hydrogen-Bond Weakening through π Systems: Resonance-Impaired Hydrogen Bonds (RIHB).
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.
['Guevara-Vela|José Manuel|JM|http://orcid.org/0000-0003-1782-6792', 'Romero-Montalvo|Eduardo|E|http://orcid.org/0000-0001-7937-0706', 'Del Río-Lima|Alejandra|A|', 'Martín Pendás|Ángel|Á|http://orcid.org/0000-0002-4471-4000', 'Hernández-Rodríguez|Marcos|M|http://orcid.org/0000-0001-8686-160X', 'Rocha Rinza|Tomás|T|http://orcid.org/0000-0003-1650-4150']
hydrogen bonds conjugation aldehydes density functional calculations pi interactions