Substituent effects on the 1H, 13C, and 15N NMR spectra of substituted benzanilides.
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概要
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The <SUP>15</SUP>N, carbonyl <SUP>13</SUP>C, and amide <SUP>1</SUP>H NMR spectra of a series of substituted benzanilides, XC<SUB>6</SUB>H<SUB>4</SUB>CONHC<SUB>6</SUB>H<SUB>4</SUB>Y, measured in four solvents of different polarity were correlated with the electronic effects of substituents by the use of the Hammett equation. Except for the <SUP>13</SUP>C chemical shift vs. the σ<SUB>x</SUB> plot, the ρ-values are positive, showing that the chemical shift tends to move down-field as the substituent becomes electron-withdrawing. Substituent effects could be assumed to arise from a cross conjugation of competing amide and benzoyl resonance structures perturbed via an inductive mechanism by the substituent on the anilino ring. The <SUP>15</SUP>N chemical shifts of XC<SUB>6</SUB>H<SUB>4</SUB>CONHC<SUB>6</SUB>H<SUB>5</SUB> can be expected to be correlated with the rotational barrier, since the down-field shift of the <SUP>15</SUP>N chemical shift (in reference to unsubstituted) benzanilide was ascribed to a steric inhibition of the aryl-carbonyl conjugation. This trend is actually shown by a plot of the <SUP>15</SUP>N chemical shift vs. the rotational barrier of a similarly substituted <I>N</I>,<I>N</I>-dimethylbenzamide. The NH group of 2-methoxy- and 2-chlorobenzanilides was shown to be intramolecularly hydrogen bonded with the ortho substituent (CH<SUB>3</SUB>O or Cl) by their <SUP>1</SUP>H NMR and infrared NH spectra.
- 公益社団法人 日本化学会の論文
著者
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SUEZAWA Hiroko
Department of Synthetic Chemistry, Faculty of Engineering, Yokohama National University
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Yuzuri Tomoaki
Department Of Advanced Materials Chemistry Graduate School Of Engineering Yokohama National Universi
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HAMADA Yoshiki
Faculty of Pharmacy, Meijo University
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Hirota Minoru
Department Of Animal Science Obihiro University Of Agriculture And Veterinary Medicine
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Ito Yoshio
Faculty Of Pharmaceutical Sciences Mukogawa Women's University
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Suezawa Hiroko
Deparment of Synthetic Chemistry, Division of Materials Science and Chemical Engineering, Faculty of Engineering, Yokohama National University
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Hirota Minoru
Deparment of Synthetic Chemistry, Division of Materials Science and Chemical Engineering, Faculty of Engineering, Yokohama National University
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ITO Yoshio
Faculty of Pharmaceutical Science, Mukogawa Women's University
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