Conformational behaviour and inclusion compound forming properties of 5,18-disubstituted derivatives of 5, 11, 12, 18-tetrahydrotribenzo[b,f,j][1,4]diazacyclododecine-6, 17-dione

W. David Ollis*, Julia Stephanidou Stephanatou, J. Fraser Stoddart, Gulten G. Unal, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

An X-ray structure analysis shows that the 5, 18-dimethyl derivative (5) of the title compound (4) crystallises from xylene as a 1:1 inclusion compound in which the host molecules adopt propeller-like conformations (7 and 7*) with almost perfect C2 symmetry. Dynamic 1H n.m.r. spectroscopy shows that the 5, 18-dibenzyl derivative (6) of (4) forms a 1:1 inclusion compound with ethanol in the solid state and undergoes ring inversion (7 ⇌ 7*) between enantiomeric propeller-like conformations in solution against a barrier of 21.1 kcal mol-1.

Original languageEnglish (US)
Pages (from-to)2225-2228
Number of pages4
JournalTetrahedron Letters
Volume22
Issue number23
DOIs
StatePublished - 1981

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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