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

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

Research output: Contribution to journalArticle

214 Scopus citations

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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