Effect of oxygen substituents on two-and three-bond carbon-proton spin-spin coupling constants

Magnetic Resonance in Chemistry

Volumn 38, Issue 5, 2000, Pages 343-359

  Morvai, Miklós ^a   Nagy, Tamás ^b   Kocsis, Ákos ^b   Szabó, László F ^b   Podányi, Benjamin ^a  

^a Chinoin Pharmaceutical and Chemical Works Ltd   (Hungary)

^b SEMMELWEIS UNIVERSITY OF MEDICINE   (Hungary)

Author keywords

Carbon proton coupling constants; Conformational analysis; Iridoids; NMR; NOE; Substituent effect; Vicinal proton proton coupling constants

Indexed keywords

COUPLINGS; DIHEDRAL ANGLE; OXYGEN;

CARBON-PROTON COUPLING CONSTANT; CONFORMATIONAL ANALYSIS; COUPLING CONSTANTS; EFFECT OF OXYGEN; IRIDOIDS; NOE; PROTON COUPLING; PROTON-PROTON COUPLING CONSTANTS; SUBSTITUENT EFFECT; VICINAL PROTON-PROTON COUPLING CONSTANT;

CARBON;

EID: 0034178731     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/1097-458X(200005)38:5<343::AID-MRC654>3.0.CO;2-7     Document Type: Article

References (44)

1. 1. Eberstadt M, Gemmecker G, Mierke DF, Kessler H. Angew. Chem., Int. Ed. Engl. 1995; 34: 1671.
2. 2. Hansen PE. Prog. Nucl. Magn. Reson. Spectrosc. 1981; 14: 175.
3. 3. Marshall JL. Carbon-Carbon and Carbon-Proton NMR Couplings: Applications to Organic Stereochemistry and Conformational Analysis. Verlag Chemie International: Deerfield Beach, FL, 1983.
4. 4. Thomas WA. Prog. Nucl. Magn. Reson. Spectrosc. 1997; 30: 183.
5. 5. Nagy T, Morvai M, Podányi B, Kocsis Á. Phytochemistry in press.
6. 6. Tietze LF, Niemeyer U, Marx P, Glüsenkamp KH. Tetrahedron 1980; 36: 735.
7. 7. Hricovini M, Tvaroska I, Uhrin D, Bata Gy. J. Carbohydr. Res. 1989; 8: 389.
8. 8. Parella T, Sánches-Ferrando F, Virgili A. Magn. Reson. Chem. 1992; 30: 823.
9. 9. Neuhaus D, Williamson M. The Nuclear Overhauser Effect in Structural and Conformational Analysis. VCH: New York, 1989.
10. 10. Kövér KE, Prakash O, Hruby VJ. J. Magn.Reson. A 1992; 99: 426.
11. 11. Uhrin D, Batta Gy, Hruby VJ, Barlow PN, Kövér KE. J. Magn. Reson. 1998; 130: 155.
12. 12. HyperChem Release 4 for Windows. Hypercube: Gainesville, FL, 1994.
13. 13. SYBYL 6.5. Tripos: St., Louis, MO, 1998.
14. 14. Patthy-Lukáts Á, Károlyházy L, Szabó LF, Podányi B. J. Nat. Prod. 1997; 60: 69.
15. 15. Eliel EL, Wilen SH, Mander LN. Stereochemistry of Organic Compounds. Wiley-Interscience: New York, 1994;
16. (a) 724;
17. (b) 758.
18. 16. (a) Altona C, Sundaralingam M. J. Am. Chem Soc. 1972; 94: 8205;
19. (b) Cremer D, Pople JA. J. Am. Chem. Soc. 1975; 97: 1354.
20. 17. Kao L-F, Barfield M. J. Am. Chem. Soc. 1985; 107: 2323.
21. 18. Tvaroska I, Taravel FR. Adv. Carbohydr. Chem. Biochem. 1995; 51: 15.
22. 19. Aydin R, Günther H. Magn. Reson. Chem. 1990; 28: 448.
23. 20. van Beuzekom AA, de Leeuw FAAM, Altona C. Magn. Reson. Chem. 1990; 28: 68.
24. 21. San Fabian J, Guilleme J, Diez E. J. Mol. Struct. 1998; 426: 117.
25. 22. Parella T, Sánches Ferrando F, Virgili A. Magn. Reson. Chem. 1994; 32: 657.
26. 23. Parella T, Sánches-Ferrando F, Virgili A. Magn. Reson. Chem. 1995; 33: 196.
27. 24. Podlasek CA, Wu J, Stripe WA, Bondo PB, Serianni AS. J. Am. Chem. Soc. 1995; 117: 8635.
28. 25. Pachler KGR. J. Chem. Soc., Perkin Trans. 2 1972; 1936.
29. 26. Colucci WJ, Jungk SJ, Gandour RD. Magn. Reson. Chem. 1985; 23: 335.
30. 27. Imai K, Ösawa E. Magn. Reson. Chem. 1990; 28: 668.
31. 28. Hansen PE. Prog. Nucl. Magn. Reson. Spectrosc. 1981; 14: 175, Section 14.
32. 29. Denisov AY, Tyshchischin EA, Tkachev AV, Mamatyuk VI. Magn. Reson. Chem. 1992; 30: 886.
33. 30. Parella T, Sánches-Ferrando F, Virgili A. Magn. Reson. Chem. 1997; 35: 30.
34. 31. Mulloy B, Frenkiel TA, Davies DB. Carbohydr. Res. 1988; 184: 39.
35. 32. Tvaroska I, Hricovíni M, Petrakova E. Carbohydr. Res. 1989; 189: 359.
36. 33. Schwarcz JA, Cyr N, Perlin AS. Can. J. Chem. 1975; 53: 1872.
37. 34. (a) Marshall JL. Carbon-Carbon and Carbon-Proton NMR Couplings: Applications to Organic Stereochemistry and Conformational Analysis. Verlag Chemie International: Deerfield Beach, FL, 1983; 29-33;
38. (b) Hines JV, Landry SM, Varani G, Tinoco Jr I. J. Am. Chem. Soc. 1994; 116: 5823.
39. 35. Cyr N, Hamer GK, Perlin AS. Can. J. Chem. 1978; 56: 297.
40. 36. Bock K, Pedersen C. Acta. Chem. Scand., Ser. B 1977; 31: 354.
41. 37. Barfield M, Walter SR. J. Am. Chem. Soc. 1983; 105: 4191.
42. 38. Hansen PE. Prog. Nucl. Magn. Reson. Spectrosc. 1981; 14: 175, Sections 8.3.3 and 17.1.
43. 39. Damtoft S, Jensen SR, Nielsen BJ. Phytochemistry 1981; 20: 2717.
44. 40. Serianni AS, Wu J, Carmichael I. J. Am. Chem. Soc. 1995; 117: 8645.