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Abstract 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 (CH…O, OH…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. This article is categorized under: Structure and Mechanism > Molecular Structures Structure and Mechanism > Reaction Mechanisms and Catalysis
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Self-assembling purine and pteridine quartets: how do π-conjugation patterns affect resonance-assisted hydrogen bonding?
Computed association strengths for 43 purine and pteridine quartets (38 to 100 kcal mol −1 ) show excellent linear correlation with π-conjugation gain in the assembled monomers ( r 2 = 0.965). Even quartets having the same secondary electrostatic interactions can display very different association strengths depending on the π-conjugation patterns of the monomeric units.
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- Award ID(s):
- 1751370
- PAR ID:
- 10213899
- Date Published:
- Journal Name:
- Organic & Biomolecular Chemistry
- Volume:
- 18
- Issue:
- 6
- ISSN:
- 1477-0520
- Page Range / eLocation ID:
- 1078 to 1081
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1039/C9OB02412C
