Stability of doubly and triply H-bonded complexes governed by acidity-basicity relationships

We used our recently proposed acidity-basicity interplay (ABI) model ( Chem. Sci. , 2018, 9 , 4402) and the Jorgensen secondary interactions hypothesis (JSIH) to rationalise the experimentally observed trends in the formation constants of doubly and triply H-bonded systems with -NH O&z.dbd;C- an...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-01, Vol.55 (11), p.1556-1559
Main Authors: Vallejo Narváez, Wilmer E, Jiménez, Eddy I, Cantú-Reyes, Margarita, Yatsimirsky, Anatoly K, Hernández-Rodríguez, Marcos, Rocha-Rinza, Tomás
Format: Article
Language:English
Subjects:
Basicity
Bonding strength
Stability
Trends
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Summary:We used our recently proposed acidity-basicity interplay (ABI) model ( Chem. Sci. , 2018, 9 , 4402) and the Jorgensen secondary interactions hypothesis (JSIH) to rationalise the experimentally observed trends in the formation constants of doubly and triply H-bonded systems with -NH O&z.dbd;C- and -NH N- interactions. Unlike the JSIH, the ABI interpretation can explain the trends in the complexation of amide/imide homo- and heterodimers as well as ADA-DAD clusters. We found that the strongest H-bonds play a very important role, a condition which offers an alternative to the well established JSIH to modulate the stability of these relevant systems. The acidity-basicity interplay model allows explaining and tuning the relative stability of doubly and triply H-bonded complexes.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc06967k