Abstract
The13C NMR chemical shifts of α,β-unsaturated sulphones of the types E-2-aryl-1-phenyl-sulphonylethylenes (series I) and E-1-arylsulphonyl-2-phenylethylenes (series II) have been measured in CDCl3 solution. The chemical shifts of the side-chain and a few ring carbons have been correlated with various single and multiparameter linear free energy relationships. Analysis of the13C NMR spectral data by a dual substituent parameter equation shows that the resonance effect is the dominant factor at C-α in series I and C-β in series II. The inductive effect is predominant at C-β in series I with a reverse substituent effect at this carbon atom. The reverse inductive contribution is explained in terms of π-polarisation mechanism.
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References
Arrowsmith J E, Cook M J and Hardstone D J 1978Org. Magn. Reson. 11 160
Baliah V and Seshapathi Rao M 1959J. Org. Chem. 24 867
Banerji A, Ghosal T and Acharyya A K 1984Indian J. Chem. B23 546
Bromilov J, Brownlee R T C and Craik D J 1977Aust. J. Chem. 30 351
Bromilow J, Brownlee R T C, Craik D J, Fiske P R, Rowe J E and Sadek M 1981J. Chem. Soc. Perkin Trans. 2 753
Brownlee R T C and Craik D J 1981J. Chem. Soc. Perkin Trans. 2 760
Buchanan G W, Zamora C R and Clarke D E 1974Can. J. Chem. 52 3895
Butt G and Topsom R D 1982Spectrochim. Acta A38 301, 649
Dawson D A and Reynolds W F 1975Can. J. Chem. 53 373
Dhami K S and Stothers J B 1965Can. J. Chem. 43 510
Ehrenson S, Brownlee R T C and Taft R W 1973Prog. Phys. Org. Chem. 10 1
Hamer G K, Peat I R and Reynolds W F 1973Can. J. Chem. 51 897
Happer D A R 1976Aust. J. Chem. 29 2607
Happer D A R, Mckerrow S M and Wilkinson A L 1977Aust. J. Chem. 30 1715
Inamoto N, Kushida K, Masuda S, Ohta, Satoh S, Tamura Y, Tokumaru K, Torik and Yoshida M 1974Tetrahedron Lett. 3617
Masumarra G and Ballistreri F P 1980Org. Magn. Reson. 14 384
Shapiro M J 1977Tetrahedron 33 1091
Solčániová E, Toma S and Gronowitz S 1976Org. Magn. Reson. 8 439
Solčániová E, Hrnciar P and Liptaj T 1982Org. Magn. Reson. 18 55
Srinivasan C, Ganesan P K and Arumugam N 1983Indian J. Chem. B22 646
Srinivasan C, Shunmugasundaram A and Arumugam N 1985Indian J. Chem. 24B 827
Swain C G and Lupton E C 1968J. Am. Chem. Soc. 90 4328
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Srinivasan, C., Ganesan, P.K., Shunmugasundaram, A. et al. 13C NMR substituent induced chemical shifts in the side-chain carbons of α,β-unsaturated sulphones. Proc. Indian Acad. Sci. (Chem. Sci.) 97, 33–39 (1986). https://doi.org/10.1007/BF02880839
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DOI: https://doi.org/10.1007/BF02880839