The carbon-13 NMR spectra and electronic structure of 3H-phenoxazin-3-ones.
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概要
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The <SUP>13</SUP>C NMR chemical shifts of 3<I>H</I>-phenoxazin-3-one (<B>1</B>) and eighteen of its derivatives are reported. The chemical shifts of <B>1</B> can be explained in terms of a successive polarization of the π-conjugated framework by an electron-withdrawing carbonyl group and a π-donating ether oxygen. The principal factor solution for the chemical shifts of the 2-substituted 3<I>H</I>-phenoxazin-3-ones suggests that the first and the second factors collectively controlling the 2-substituent effect are electronic and steric effects, respectively. A dual substituent parameter analysis elucidated the transmission modes of the polar and resonance effects of the 2-substituents, and that the first and the fourth factor loadings multiplied by the corresponding standard deviation of the chemical shifts correlate with the CNDO/2 substituent-induced σ and π charge densities.
- 公益社団法人 日本化学会の論文
著者
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Ueno Yoshio
Department Of Applied Chemistry Nagoya Institute Of Technology
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Hasegawa Kan-ichi
Department of Natural Science, Nagoya University of Arts
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