Correlation of 13C shifts with substituent parameters in 3,4-diphenyl-1,2,5-oxadiazole 2-oxides substituted at the para-positions of either or both phenyl rings.

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概要

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• C-1′, C-1″, C-3, and C-4 <SUP>13</SUP>C shifts in 3,4-di(4′-or/and 4″-X)phenyl-1,2,5-oxadiazole 2-oxides (3,4-diarylfurazan 2-oxides; three series: X=NMe<SUB>2</SUB>, OMe, Me, Cl, H, and NO<SUB>2</SUB>) were correlated vs. seven different divided substituent parameter sets. Results have implied that i) the C-3–C-4 bond does not transmit mesomeric effects efficiently; ii) no effects can be specifically attributed to the possibility that the C-3 aryl maintains a higher dihedral angle with respect to the furoxan ring than the C-4 aryl; iii) there appears to be a directionality to the propagation of localized π-polarization due to lesser ability of C=N(O)→O to convey effects compared with C=N(O); and, iv) the furazan <I>N</I>-oxide ring, being generally an electron acceptor, transmits substituent effects nonlinearly.

• 公益社団法人 日本化学会の論文

著者

• Singh D.

  Department Of Electronics And Computer Engineering Indian Institute Of Technology Roorkee

• Singh D.

  Department of Organic Chemistry, Indian Institute of Science

• Balasubrahmanyam S.

  Department of Organic Chemistry, Indian Institute of Science

• Rajendran N.

  Department of Organic Chemistry, Indian Institute of Science

• SINGH D.

  Department of Chemical Engineering, Institute of Technology, Banaras Hindu University

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