Resonance-assisted hydrogen bond

The resonance assisted hydrogen bond (commonly abbreviated as RAHB) is a strong type of hydrogen bond.

Causes

It is caused by the π-delocalization that involves the hydrogen and cannot be properly described by the electrostatic model alone. This description of the hydrogen bond has been proposed to describe unusually short distances generally observed between O=C-OH∙∙∙ or ∙∙∙O=C-C=C-OH.^[1]

References

↑ http://www.ggilli.com/files/2010_SYNGENTA_STEIN_CH_LECTURE_FUNCTIONAL_H-BOND.ppt

Chemical bonds

Intramolecular
("strong")

Covalent bond

By symmetry	Sigma (σ) Pi (π) Delta (δ) Phi (φ)

By multiplicity	1 (single) 2 (double) 3 (triple) 4 (quadruple) 5 (quintuple) 6 (sextuple)

Miscellaneous	Agostic bond Bent bond Dipolar bond Pi backbond Charge-shift bond Hapticity Conjugation Hyperconjugation Antibonding

Resonant bonding	Electron deficiency 3c–2e 4c–2e Hypercoordination 3c–4e Aromaticity möbius super sigma homo spiro σ-bishomo spherical

Metallic bonding

Metal aromaticity

Ionic bonding

Intermolecular
("weak")

van der Waals forces	London dispersion force

Hydrogen bond	Low-barrier Resonance-assisted Symmetric Dihydrogen bonds C–H···O interaction

Other noncovalent	Mechanical bond Halogen bond Aurophilicity Intercalation Stacking Cation–pi bond Anion–pi bond Salt bridge

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