1H and 13C NMR spectral study of some 2r-Aryl-6c-phenylthian-4-ones, their 1-oxides and 1,1-dioxides

Spectroscopy Letters

Volumn 42, Issue 3, 2009, Pages 147-155

  Devanathan, D ^a   Pandiarajan, K ^a  

^a ANNAMALAI UNIVERSITY   (India)

Author keywords

13C NMR; 1H NMR; Thian 4 one 1; Thian 4 one 1 oxides; Thian 4 ones

Indexed keywords

EID: 70449336363     PISSN: 00387010     EISSN: 15322289     Source Type: Journal    
DOI: 10.1080/00387010902772153     Document Type: Article

References (27)

1. Ramalingam, K.; Berlin, K. D.; Satyamurthy, N.; Sivakumar, R. Carbon-13 shifts in 1-hetera-2,6-diaryl-4-cyclohexanones and a few corresponding 1-hetera-4-cyclohexanols. J. Org. Chem. 1979, 44, 471-478.
2. 13C NMR spectra of some 2,6-diarylpi-peridin-4-ones. Magn. Reson. Chem. 1985, 23, 292-295.
3. 13C NMR spectral studies of some 2,6-diarylpiperidin-4-ones. Indian J. Chem. B 1987, 26, 624-627.
4. Pandiarajan, K.; Sekar, R.; Anandharaman, R.; Ramalingam, V.; Marko, D. Conformational studies of some piperidin-4-ones using PMR spectroscopy. Indian J. Chem. B 1991, 30, 490-493.
5. 17O NMR and quantum-chemical study of the stereochemistry of the sulfoxide and sulfone derivatives of 3-arylidene-1-thioflavan-4-one epoxides. Magn. Reson. Chem. 2003, 41, 193-201.
6. 1,3-Strain mediated epimerization of 2e,3e,5e,6e-tetraarylpiperidin-4-one oximes. Magn. Reson. Chem. 2004, 42, 1056-1059.
7. Pandiarajan, K.; Sabapathy Mohan, R. T.; Gomathi, R.; Muthukumaran, G. Synthesis and NMR spectral study of some t(3)-aryl-r(2),c(4)-bisethoxycarbonyl-t(5)-hydroxy-c(5)-methylcyclohexanones. Magn. Reson. Chem. 2005, 43, 430-434.
8. Pandiarajan, K.; Sabapathy Mohan, R. T.; Murugavel, K.; Hema, R. Synthesis and conformational study of some r(2),c(4)-bis(isopropoxy-carbonyl)-t(3)-aryl-c(5)-hydroxy-t(5)-methylcyclohexanones using NMR spectra. J. Mol. Struct. 2008, 875, 226-235.
9. 13C NMR signal assignments of some new spiro[7H-benzo[de]anthracenenaphthopyr-ans]. Magn. Reson. Chem. 2008, 46, 295-298.
10. 13C COSY NMR and mass spectroscopy in structure elucidation-class of compounds. Spectrosc. Lett. 2008, 41, 15-18.
11. 13C NMR spectral data for benzoylecgonine, a cocaine metabo-lite. Spectrosc. Lett. 2008, 41, 101-103.
12. 1H NMR spectral study of some 2,6-diphenylthian-4-ones and their 1,1-dioxides. Indian J. Chem. B 2003, 42, 1711-1715.
13. Baliah, V.; Chellathurai, T. Conformational studies on heterocyclic compounds: part I - preparation & stereochemistry of some substi-tuted tetrahydrothiapyran-4-ones & tetrahydrothiapyran-4-ols. Indian J. Chem. B 1971, 9, 424-429.
14. Thiruvalluvar, A.; Balamurugan, S.; Butcher, R. J.; Pandiarajan, K.; Devanathan, D. 2-(4-Fluorophenyl)-6-phenyltetrahydro-2H-thiopyran-4-one 1-oxide. Acta Crystallogr. E 2007, 63, 04486.
15. Silverstein, R. M.; Webster, F. X. Spectrometric Identification of Organic Compounds; 6th ed, Wiley: New York, 1998; 229 pp.
16. Johnson, C. R.; McCants, D. Jr. The stereochemistry of oxidation of sulfur. Oxidation of 4-substituted thianes to sulfoxides. J. Am. Chem. Soc. 1965, 87, 1109-1114.
17. Van Acker, L.; Anteunis, M. Difference in the conformational preference of the sulfur-oxygen bond in 1,3-dithiane 1-oxides and 1,3-oxathiane 3-oxides. Tetrahedron Lett. 1974, 2, 225-228.
18. Khan, S. A.; Lambert, J. B.; Hernandez, O.; Carey, F. A. Oxides of 1,3-dithiane and 1,3,5-trithiane. The diamagnetic anisotropy of carbon-sulfur bonds. J. Am. Chem. Soc. 1975, 97, 1468-1473.
19. Harpp, D. N.; Gleason, J. G. Conformational analysis of sulfur-containing heterocycles. A dipolar effect. J. Org. Chem. 1971, 36, 1314-1316.
20. Bass, S. W.; Evans, S. A. Jr. Carbon-13 nuclear magnetic resonance spectral properties of alkyl disulfides, thiosulfinates and thiosulfo-nates. J. Org. Chem. 1980, 45, 710-715.
21. 13C NMR studies of the mono-S-oxides of 1,2-, 1,3- and 1,4-dithianes. Tetrahedron 1984, 40, 1477-1485.
22. Lambert, J. B.; Netzel, D. A.; Sun, H. N.; Lilianstrom, K. K. Carbon-13 chemical shifts of the pentamethylene heterocycles. J. Am. Chem. Soc. 1976, 98, 3778-3783.
23. Karplus, M. Contact electron-spin coupling of nuclear magnetic moments. J. Chem. Phys. 1959, 30, 11-15.
24. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. The relationship between proton-proton NMR coupling constants and substituent electronegativities-I an empirical generalization of the Karplus equation. Tetrahedron 1980, 36, 2783-2792.
25. 3J(C,H) coupling constants via -S-, -S(O)- and -SO2-: their determination, calculation and comparison of detection methods. Magn. Reson. Chem. 2004, 42, 667-670.
26. 1H chemical shifts. Magn. Reson. Chem. 2006, 44, 491-509.
27. Gurumani, V.; Pandiarajan, K.; Swaminathan, M. Conformational studies of some 1-hetera-2,6-diphenylcyclohexan-4-one oximes using NMR spectra - evidence for boat form contributions to trans-2,6-diphenyl systems. Bull. Chem. Soc. Japan 1997, 70, 29-35.