Structure of a 2-arylquinoline dimer, a compound with a new ring system.
The title compound, 6,15-dimethyltribenzo-[c,f,j]naphtho[1,2,3,4-lmn][2,7]phe nanthroline was obtained in low yield from the reaction of 2-(4-methylphenyl)quinoline and various aryllithiums. The compound is a 'dimer' in which two phenylquinoline units are joined by three bonds; the dimer has exact twofold symmetry. Non-bonded interactions produce substantial out-of-plane distortions. Bond lengths between the two phenylquinoline halves suggest that the two phenylquinoline pi-electron systems are more-or-less undisturbed and linked by single bonds. Molecular-mechanics optimizations of models with inversion (1) and twofold symmetry suggest that the latter conformation is the more stable of the two to a slight extent.
Ammon
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Department of Chemistry and Biochemistry, University of Maryland, College Park 20742.
Reid
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D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D010618:Phenanthrolines / Q000737:chemistry*
D010618:Phenanthrolines; C084280:6,15-dimethyltribenzo-(c,f,j)naphtho(1,2,3,4-lmn)(2,7)phenanthroline