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Carbon-13 NMR investigation of 2,5-diaryl-1,4-dithiins

✍ Scribed by C. M. Buess; K. S. Narayanan; D. J. O'Donnell; P. Arjunan; K. D. Berlin

Publisher: John Wiley and Sons
Year: 1979
Tongue: English
Weight: 460 KB
Volume: 12
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270121209

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✦ Synopsis

Abstract

The ^13^C NMR spectra of eight 2,5‐diaryl‐1,4‐dithiins were recorded and signals were assigned. A linear correlation was observed between the electronegativity of the substituent groups on C‐10,10′ and the chemical shifts of C‐10,10′ after applying corrections for the magnetic anisotropic effect of the substituents. A Hammett correlation was found between the ^13^C chemical shifts of C‐3,6 and C‐7,7′ and the σ~p~^+^ parameter associated with the substituents on C‐10,10′. Extended electronic interaction between the π system of the aryl group and the π system of the dithiin ring was suggested by the observance of an alternating behavior in the magnitude of the substituent effects on the ^13^C shifts of C‐2,5 and C‐3,6. An alternating effect was also noted in the magnitude of the long‐range ^13^CF coupling constants for these same carbon signals in 2,5‐(10,10′‐difluoro)diphenyl‐1,4‐dithiin.

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