Simultaneous Hydrogen Bonds with Different Binding Modes: The Acceptor "Rules" but the Donor "Chooses".
Marianne Rica Garcia1, Iñigo Iribarren1, Isabel Rozas1
1School of Chemistry, Trinity College Dublin, The University of Dublin, 154-160 Pearse Street, D02 R590, Dublin, Ireland.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 26, 2023
Summary
Hydrogen bonds (HB) exhibit distinct binding modes, influencing interaction strength in biological and catalytic systems. Substituents on HB donors modulate these interactions, with acceptors largely determining patterns and donors making the final selection.
Area of Science:
- Computational chemistry
- Molecular interactions
- Supramolecular chemistry
Background:
- Hydrogen bonds (HB) are crucial in biological and catalytic processes.
- Understanding HB binding modes and their electronic effects is essential.
- The role of substituents on HB donors requires further investigation.
Purpose of the Study:
- To computationally investigate different hydrogen bond binding modes.
- To analyze the electronic effects of substituents on HB donors.
- To compare computational findings with experimental data.
Main Methods:
- Computational modeling of HB interactions.
- Analysis of electronic effects using electron-withdrawing (EWG) and electron-donating (EDG) groups.
- Comparison with crystal structures from the Cambridge Structural Database (CSD).
Main Results:
- Three binding modes were identified: bifurcated, parallel, and zigzag.
- Parallel HBs were generally the strongest, followed by bifurcated and zigzag.
- A competition between bifurcated and zigzag modes was observed.
- Computational trends were consistent with experimental data.
Conclusions:
- HB acceptor groups primarily dictate interaction patterns and strength.
- HB donors select the binding mode when multiple options exist.
- Substituents significantly influence HB interactions and binding preferences.
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