The magnitude of [C-H···O] hydrogen bonding in molecular and supramolecular assemblies

Francisco Raymo, M. D. Bartberger, K. N. Houk, J. F. Stoddart

Research output: Contribution to journalArticle

212 Citations (Scopus)

Abstract

Ab initio calculations at the MP2/6-311++G** level on model systems (N-methylpyridinium complexes of dimethyl ether and dimethyl phosphate anion) provide quantitative measures of the large stabilization energies that arise from [C-H···O] contacts in charged systems. These attractive interactions control (i) the self-assembly of bipyridinium-based catenanes and rotaxanes in solution, (ii) the self-organization of left-handed Z-DNA with alternating [dC-dG] sequences in the solid state, and (iii) the binding of pyridinium derivatives with single- and double-stranded DNA. Slightly attractive interactions occur between the donor ether and phosphate moieties and a neutral pyridine molecule in the gas phase. Electrostatic potential and solvation calculations demonstrate that [C-H···O] interactions which involve a cationic [C-H] donor are dominated by electrostatic terms.

Original languageEnglish
Pages (from-to)9264-9267
Number of pages4
JournalJournal of the American Chemical Society
Volume123
Issue number38
DOIs
StatePublished - Sep 26 2001

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Z-Form DNA
Hydrogen Bonding
Static Electricity
Catenanes
Electrostatics
Ethers
Hydrogen bonds
Phosphates
DNA
Rotaxanes
Single-Stranded DNA
Solvation
Ether
Pyridine
Self assembly
Anions
Negative ions
Stabilization
Gases
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

The magnitude of [C-H···O] hydrogen bonding in molecular and supramolecular assemblies. / Raymo, Francisco; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F.

In: Journal of the American Chemical Society, Vol. 123, No. 38, 26.09.2001, p. 9264-9267.

Research output: Contribution to journalArticle

Raymo, Francisco ; Bartberger, M. D. ; Houk, K. N. ; Stoddart, J. F. / The magnitude of [C-H···O] hydrogen bonding in molecular and supramolecular assemblies. In: Journal of the American Chemical Society. 2001 ; Vol. 123, No. 38. pp. 9264-9267.
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