Investigation of the Solvent Enclathration Potentials of 5-Phenyl-10, 11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol and Related Seven-membered Ring Alcohols

  • Benjamin Taljaard
  • Benita Barton
  • Cedric W McCleland
Keywords: EnclathrationInclusion complexes, Medium rings, Seven-membered rings, 5-phenyl-5H-dibenzo[a, d]cyclohepten-5-ol, 11-phenyl-6, 11-dihydrodibenzo[b, e]oxepine11-phenyl-6, 11- dihydrodibenzo[b, e]thiepine


Four previously reported tricyclic alcohols containing seven-membered central B-rings, 5-phenyl-10, 11-dihydro-5Hdibenzo [a,d]cyclohepten-5-ol, 5-phenyl-5H-dibenzo[a,d]cyclohepten-5-ol, 11-phenyl-6, 11-dihydrodibenzo[b,e]oxepin-11-ol and 11-phenyl-6, 11-dihydrodibenzo[b,e]thiepin-11-ol have been synthesized and their solvent enclathration (inclusion) properties investigated and compared by using 1H-NMR and differential scanning calorimetry (DSC). The presence of an oxygen or a sulphur atom, respectively, in the B-ring of the latter two compounds had a detrimental effect on the solvent enclathration properties of the host compounds as compared to those containing an ethane or ethylene bridge. This suggests that, although enclathration is highly dependent on the hydrogen bonding ability of the host, rigidity of the structure plays a crucial role in the formation and stability of these complexes.

South African Journal of Chemistry Vol.57 2004: 44-48

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