High-resolution nuclear magnetic resonance spectra of phenanthrenes—II Halogeno-, cyano-, nitro- and carbonyl phenanthrenes, and phenanthrene-9,10-quinone

摘要: Abstract The 60 Mc/s NMR spectra of 9-fluoro-, 9-chloro-, 9,10-dibromo-, 9-iodo-, 3-acetyl-9-bromo-, 9-cyano-, 9-cyano-10-methyl-, 1-, 2-, 3- and 9-nitro-, 9-bromo-10-nitro-, 9-acetyl-, 4- 9-methoxycarbonyl- 9,10-dimethoxycarbonyl-, 9-formyl-, 3-ethyl-9-carboxyl-, 9-phenyl-10-carboxylphenanthrenes have been recorded analysed, usually as ABX ABMX, followed by computer refinement. Coupling constants are generally similar to their values in phenanthrene; an inter-ring HF coupling, well the expected H(10)F is observed 19F spectrum 9-fluorophenanthrene. shift H(8) 9-halogenophenanthrenes can be interpreted terms magnetic anisotropy electric field effects, but H(10) dominated some factor characteristic high C(9)C(10) bond order. Ortho effects nitro acetyl also depend on order intermediate bond. cyano group seems largest contributor shifts both 9-cyanophenanthrene CH3 9-cyano-10-methyl phenanthrene. H(9) 3-nitrophenanthrene sufficiently different permit measurement J9,10. presence a 10-substituent greatly reduces peri carbonyl groups. By use 2,7-dimethyl derivative, phenanthrene-9,10-quinone has unambiguously assigned.