Synthesis and conformational behaviour of tri-3-methyltrianthranilides. A new example of spontaneous resolution and inclusion compound formation on crystallisation |
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Authors: | Simon J. Edge W.David Ollis Julia Stephanidou Stephanatou J.Eraser Stoddart David J. Williams Kwamena A. Woode |
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Affiliation: | Department of Chemistry, The University, Sheffield S3 7HF UK;Chemical Crystallography Laboratory, Imperial College, London SW7 2AY UK |
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Abstract: | The tri-3-methyltrianthranilide derivatives ()–() have been synthesised. Dynamic 1H n.m.r. spectroscopy indicates that the ,′,″-trimethyl derivative () exists in solution as slowly ring inverting ( ? *) enantiomeric helical conformations. X-Ray crystallography shows that the ,′-dimethyl-″-benzyl derivative () undergoes spontaneous resolution when it crystallises as a 1:1 adduct from toluene. The host molecules adopt a helical conformation (Figure 1) within a lattice structure that contains chiral channels (Figure 2) occupied by guest solvent molecules. |
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