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RESEARCH PRODUCT
Conformational properties of methylene bridged resorcarenes
Volker BöhmerIris ThondorfJörg Brennsubject
Hydrogen bondChemistryOrganic ChemistryResorcinolResorcinareneBiochemistryCrystallographychemistry.chemical_compoundCone (topology)Computational chemistryIntramolecular forceDrug DiscoveryCalixareneMethyleneConformational isomerismdescription
Abstract Conformations and conformational interconversions of resorcarene 1c have been studied by molecular mechanics calculations. As with calix[4]arenes the general stability of the four basic conformations is cone > partial cone > 1,2-alternate > 1,3-alternate. The lowest energy is calculated for a pinched cone conformer with C2v symmetry stabilised by intramolecular hydrogen bonds of the two “parallel” resorcinol units as donors. The topomerisation of the cone conformation proceeds via the partial cone and 1,2-alternate intermediates with a calculated barrier of 9.9 kcal mol−1 which is in excellent agreement with the experimental value.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1998-10-01 | Tetrahedron |