[6 + 6] Schiff-base macrocycles with 12 imines: giant analogues of cyclohexane.
Hexagon-shaped [6 + 6] Schiff-base macrocycles with 12 imine bonds are reported. These giant macrocycles possess 6 N2O2 coordination environments and mass spectrometry evidence for hexametallation of one macrocycle is provided. Semi-empirical calculations reveal two stable conformations with boat and chair geometries for the macrocycles metallated with Ni(II), analogous to the conformations observed for cyclohexane.
Hui
Joseph K-H
JK
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, CanadaV6T 1Z1.
MacLachlan
Mark J
MJ
D003510:Cyclohexanes / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013237:Stereoisomerism
D003510:Cyclohexanes; D007097:Imines; D047028:Macrocyclic Compounds; D012545:Schiff Bases; C506365:Cyclohexane; D009532:Nickel