Configurational isomerization of push-pull thiazolidinone derivatives controlled by intermolecular and intramolecular RAHB: 1H NMR dynamic investigation of concentration and temperature effects

Journal of Physical Organic Chemistry

Volumn 17, Issue 2, 2004, Pages 118-123

  Marković, Rade ^a,b   Shirazi, Ata ^c   Džambaski, Zdravko ^b   Baranac, Marija ^a,b   Minić, Dragica ^d  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

1H NMR spectroscopy; Hydrogen bonding; Push pull alkenes; Temperature effect; Z E isomerization

Indexed keywords

ASSOCIATION REACTIONS; COMPOSITION EFFECTS; DERIVATIVES; HYDROGEN BONDS; ISOMERIZATION; ISOMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; THERMAL EFFECTS;

RESONANCE-ASSISTED HYDROGEN BOND FORMATION; TEMPERATURE DEPENDENCE; THIAZOLIDINONE DERIVATIVE;

MOLECULAR DYNAMICS;

EID: 0442280598     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.700     Document Type: Article

References (34)

1. Wash PL, Maverick E, Chiefari J, Lightner DA. J. Am. Chem. Soc. 1997; 119: 3802-3806.
2. Jeffrey AG. An Introduction to Hydrogen Bonding. Oxford University Press: New York, 1997.
3. Kessler H. Angew. Chem., Int. Ed. Engl. 1982; 21: 512-523.
4. Dado GP, Desper JM, Gelman SH. J. Am. Chem. Soc. 1990; 112: 8630-8632.
5. Lewis FD, Stern CL, Yoon BA. J. Am. Chem. Soc. 1992; 114: 3131-3133.
6. Marlin DS, Olmstead MM, Mascharak PK. J. Mol. Struct. 2000; 554: 211-223.
7. Lehn J-M. Angew. Chem., Int. Ed. Engl. 1990; 29: 1304-1319.
8. Marković R, Baranac M. Heterocycles 1998; 48: 893-903.
9. Marković R, Baranac M. Synlett 2000; 607-610.
10. Marković R, Džambaski Z, Baranac M. Tetrahedron 2001; 57: 5833-5841.
11. Faulkner DJ. Nat. Prod. Rep. 1998; 15: 113-158.
12. Sokolenko N, Abbenante G, Scanlon MJ, Jones A, Gahan R, Hanson GR, Fairlie DP. J. Am. Chem. Soc. 1999; 121: 2603-2604.
13. Stevens E, Sugawara N, Bonora GM, Toniolo C. J. Am. Chem. Soc. 1980; 102: 7048-7050.
14. Pease LG, Watson C. J. Am. Chem. Soc. 1998; 100: 1279-1286.
15. Pysh ES, Toniolo C. J. Am. Chem. Soc. 1977; 99: 6211-6219.
16. Nogales DF, MA J-S, Lightner DA. Tetrahedron 1993; 49: 2361-2372.
17. Cordier F, Grzesiek S. J. Am. Chem. Soc. 1999; 121: 1601-1602.
18. Tjandra N, Bax A. J. Am. Chem. Soc. 1997; 119: 8076-8082.
19. Elnagdi MH, Elmoghayar MRH, Elgemeie EH. Synthesis 1984; 1-26.
20. Sandström J. Top. Stereochem. 1983; 14: 83-181.
21. Rajappa S. Tetrahedron 1999; 55: 7065-7114.
22. Kleinpeter E, Koch A, Heydenreich M, Chatterjee SK, Rudorf W-D. J. Mol. Struct. 1995; 356: 25-33.
23. Pappalardo RR, Marcos ES, Ruiz-López MF, Rinaldi D, Rivail J-L. J. Am. Chem. Soc. 1993; 115: 3722-3730.
24. Gómez-Sanches A, Paredes-León R, Cámpora J. Magn. Reson. Chem. 1998; 36: 154-162.
25. Babudri F, Cicciomessere AR, Farinola GM, Fiandanese V, Marchese G, Musio R, Naso F, Sciacovelli O. J. Org. Chem. 1997; 62: 3291-3298.
26. Chiara JL, Gómez-Sanches A, Bellanato J. J. Chem. Soc., Perkin Trans. 2 1998; 1797-1806.
27. Kleinpeter E, Heydenreich M, Woller J, Wolf G, Koch A, Kempter G, Pihlaja K. J. Chem. Soc., Perkin Trans. 1998; 1877-1888.
28. McMullen CH, Stirling CJM. J. Chem. Soc. B 1966; 1217-1220.
29. Ceder O, Stenhede U, Dahlquist K-I, Waisvisz JM, van der Hoeven MG. Acta Chem. Scand. 1973; 27: 1914-1924.
30. Ángyán JG, Poirier RA, Kucsman Å, Csizmadia IG. J. Am. Chem. Soc. 1987; 109: 2237-2245.
31. Gili P, Bertolasi V, Ferretti V, Gilli G. J. Am. Chem. Soc. 2000; 122: 10405-10417.
32. Gung BW, MacKay JA, Zou D. J. Org. Chem. 1999; 64: 700-706.
33. Furlani TR, Gao J. J. Org. Chem. 1996; 61: 5492-5497.
34. Winningham JM, Sogah DY. J. Am. Chem. Soc. 1994; 116: 11173-11174.