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Hydrogen bonding principles are at the core of supramolecular design. This overview features a discussion relating molecular structure to hydrogen bond strengths, highlighting the following electronic effects on hydrogen bonding: electronegativity, steric effects, electrostatic effects, π-conjugation, and network cooperativity. Historical developments, along with experimental and computational efforts, leading up to the birth of the hydrogen bond concept, the discovery of nonclassical hydrogen bonds (C-H…O, O-H…π, dihydrogen bonding), and the proposal of hydrogen bond design principles (e.g., secondary electrostatic interactions, resonance-assisted hydrogen bonding, and aromaticity effects) are outlined. Applications of hydrogen bond design principles are presented.
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Lucas J. Karas
Chia‐Hua Wu
Ranjita Das
Wiley Interdisciplinary Reviews Computational Molecular Science
University of Houston
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Karas et al. (Sat,) studied this question.
www.synapsesocial.com/papers/69db97c7387cf70698688595 — DOI: https://doi.org/10.1002/wcms.1477