Correlation of $^{13}C$ 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

Balasubrahmanyam, SN and Rajendran, N and Singh, DK (1989) Correlation of $^{13}C$ 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. In: Bulletin of the Chemical Society of Japan, 62 (10). pp. 3334-3342.

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Abstract

C-1′, C-1″, C-3, and C-4 $^{13}C$ 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=NMe2, OMe, Me, Cl, H, and $NO_2)$ 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 N-oxide ring, being generally an electron acceptor, transmits substituent effects nonlinearly.

Item Type:	Journal Article
Publication:	Bulletin of the Chemical Society of Japan
Publisher:	The Chemical Society of Japan
Additional Information:	Copyright of this article belongs to The Chemical Society of Japan
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	11 Feb 2008
Last Modified:	19 Sep 2010 04:41
URI:	http://eprints.iisc.ac.in/id/eprint/12695

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