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Note | Special issue | Vol 73, No. 1, 2007, pp.883-889
Published online, 14th September, 2007
DOI: 10.3987/COM-07-S(U)53
Nitrogen 14 NMR and Correlations of Oxidation Potentials of Dibenzo[a,d]cycl[2.2.3]azines with the Corresponding HOMOs: Further Evidence for Peripheral Conjugate System

Kiyoshi Matsumoto,* Hirokazui Iida, Seisuke Mimori, Hiroshi Hamana, and Takane Uchida

*Faculty of Pharmacy, Chiba Institute of Science, Shiomi-cho 15-8, Choshi, Chiba 288-0025, Japan


For the first time, 14N NMR spectra of a novel type of heterocycles, dibenzo[a,d]cycl[2.2.3]azines were described. The chemical shifts are almost independent of substituents at position 2. The correlations of oxidation potentials with HOMO energies of dibenzo[a,d]cycl[2.2.3]azines also offer very good correlation coefficients (r2>0.92) regardless of calculation methods at various levels. Thus, it was concluded that the contribution of the unshared electron pairs of the central nitrogen to the peripheral conjugation in this system is almost negligible.