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...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-11, Vol.23 (65), p.16605-16611
Main Authors: Guevara-Vela, José Manuel, Romero-Montalvo, Eduardo, Del Río-Lima, Alejandra, Martín Pendás, Ángel, Hernández-Rodríguez, Marcos, Rocha Rinza, Tomás
Format: Article
Language:English
Subjects:
aldehydes
conjugation
density functional calculations
hydrogen bonds
pi interactions
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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201703436