C-13 NMR study of substituent effects in 1,2,4-oxadiazole and 1,2,4-thiadiazole derivatives


Agirbas H., Kara Y. S.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.179, ss.1435-1443, 2004 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 179 Konu: 7
  • Basım Tarihi: 2004
  • Doi Numarası: 10.1080/10426500490463646
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Sayfa Sayıları: ss.1435-1443

Özet

C-13 chemical shifts of C=N, C=O and C=S carbons of 3,4-distibstituted-1,2,4-oxadiazole-5-ones(thiones) and 3,4-disubstituted-1,2,4-thiadiazole-5-ones have been determined ill CDCl3 solution. Exceptionally good Hammett correlations of C-13 NMR chemical shifts of these carbons with sigma were obtained. The negative p valites observed (inverse substituent effects) indicate pi-polarization of the C=N, C=O and C=S bonds. As expected, the long distance C=O and C=S C-13 chemical shifts were found less susceptible to substituent-induced electronic changes.