Journal of Organic Chemistry p. 5105 - 5108 (1985)
Update date:2022-07-29
Topics:
Sekiguchi, Shizen
Hirai, Motohiko
Ota, Etsuro
Hiratsuka, Hiroshi
Mori, Yuji
Tanaka, Shigeyuki
The electronic structures of 1,3-dinitro-4-phenanthryl methyl ether (2) and its 4,4-dimethoxy-1,3-dinitrophenanthrene Meisenheimer complex (3), formed from 2 and NaOCH3, were studied by UV-visible and NMR spectra and compared with the results calculated by a semiempirical Pariser-Parr-Pople method.The electronic transitions in the ether 2 and complex 3 were assigned to *? <*> ?.Calculated transition energies and oscillator strengths agree well with the observed values.Calculations showed that in the S0 state of complex 3 90.3percent of one negative charge donated by -OCH3 is distributed on the 1- and 3-NO2 groups and that in the S1 <*> S0 transition of the complex the ? formal charge is further spread over the 1- and 3-NO2 groups.A kinetic measurement in CH3OH at 25 deg C gave a little smaller equilibrium constant for formation of 3 than that for the similar naphthalene anionic ? complex.
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