Variable-temperature NMR study of the enol forms of benzoylacetones

Magnetic Resonance in Chemistry

Volumn 43, Issue 12, 2005, Pages 992-998

  Borisov, Evgueni V ^a   Skorodumov, Evgueni V ^a   Pachevskaya, Valentina M ^b   Hansen, Poul Erik ^c  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c ROSKILDE UNIVERSITY   (Denmark)

Author keywords

13C; 1H; Deuterium isotope effects on chemical shifts; Enol forms; NMR; O1H coupling constants; Potential wells; diketones

Indexed keywords

CHEMICAL SHIFT; EQUILIBRIUM CONSTANTS; KETONES; TEMPERATURE;

13C; 1H; BENZOYLACETONE; COUPLING CONSTANTS; DEUTERIUM ISOTOPE EFFECT; DEUTERIUM ISOTOPE EFFECT ON CHEMICAL SHIFT; ENOL FORM; O1H COUPLING CONSTANT; POTENTIAL WELLS; Β-DIKETONES;

DEUTERIUM;

EID: 28644441163     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1673     Document Type: Article

References (32)

1. Chan SI, Lin L, Clutter D, Dea P. Proc. Natl. Acad. Sci. U. S. A. 1970; 65: 816.
2. Bratan S, Strohbusch F. Chem. Ber. 1972; 105: 2284.
3. Shapet'ko NN, Bogachev YuS, Khatipov SA. Zh. Fiz. Khim. 1988; 62: 2632.
4. Baugham SL, Smith Z, Wilson WB, Duerst RW. J. Am. Chem. Soc. 1984; 106: 2260.
5. Emsley J. Structure and Bonding, vol. 57. Springer-Verlag: Berlin, 1984; 147.
6. Emsley J, Freeman NJ, Bates PA, Hursthouse MB. J. Chem. Soc., Perkin Trans. 1 1988; 297.
7. Bolvig S, Hansen PE. Magn. Reson. Chem. 1996; 34: 467.
8. Borisov EV, Khlebnikova TS. Dokl. Acad. Nauk, BSSR 1987; 31: 359.
9. Gilli G, Belluci F, Ferretti V, Bertolasi V. J. Am. Chem. Soc. 1989; 111: 1023.
10. Bertolasi V, Gilli P, Ferretti V, Gilli G. J. Am. Chem. Soc. 1991; 113: 4917.
11. Gilli G, Bertolasi V. In The Chemistry of Enols, Rappoport Z (ed). John Wiley & Sons: New York, 1990; 713.
12. Borisov EV, Zhang W, Bolvig S, Hansen PE. Magn. Reson. Chem. 1998; 36: S104.
13. Madsen GKH, Iversen BB, Larsen FK, Kapon M, Reisner GM, Herbstein FH. J. Am. Chem. Soc. 1998; 120: 10 040.
14. Schiott B, Madsen GKH, Bruice TC. J. Am. Chem. Soc. 1998; 120: 12 117.
15. Borisov EV. Russ. Chem. Bull. 2000; 49: 758.
16. Perrin CL, Nielson JB, Kim Y-J. Ber. Bunsen-Ges. Phys. Chem. 1998; 102: 403.
17. Perrin CL, Kim Y-J. J. Am. Chem. Soc. 1998; 120: 12 641.
18. Perrin CL, Nielson JB. Annu. Rev. Phys. Chem. 1997; 48: 511.
19. Gilli P, Bertolasi V, Pretto L, Ferretti V, Gilli G. J. Am. Chem. Soc. 2004; 126: 3845.
20. Borisov EV, Peregudov AS, Postovoi SA, Fedin EI, Kravtsov DN. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1986; 449.
21. Bolvig S, Hansen PE. Curr. Org. Chem. 2000; 4: 19.
22. Hansen PE, Bolvig S. Magn. Reson. Chem. 1997; 35: 520.
23. Hansen PE. Magn. Reson. Chem. 1986; 24: 903.
24. Bolvig S, Hansen PE, Morimoto H, Wemmer D, Williams P. Magn. Reson. Chem. 2000; 38: 525.
25. Abildgaard J, Bolvig S, Hansen PE. J. Am. Chem. Soc. 1998; 120: 9063.
26. Filarowski A, Koll A, Glowiak T. Monatsch. Chem. 1999; 130: 1097.
27. Chen LS, Cummings SC. Inorg. Chem. 1978; 17: 2358.
28. Bax A, Freeman R. J. Am. Chem. Soc. 1982; 104: 1099.
29. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Kiene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision B.03. Gaussian Incorporated: Wallingford, 2004.
30. Becke D. Phys. Rev. A. 1988; 38: 3098.
31. Ditchfield R. Mol. Phys. 1974; 27: 789.
32. Wolinski K, Hilton FF, Pulay P. J. Am. Chem. Soc. 1990; 112: 8251.