Conformational analysis of fluoroacetoxime and of its O-methyl ether by 1H, 13C and 15N NMR and theoretical calculations

Journal of Physical Organic Chemistry

Volumn 17, Issue 1, 2004, Pages 42-48

  Tormena, Cláudio F ^a   Rittner, Roberto ^a   Abraham, Raymond J ^b   Basso, Ernani A ^c   Fiorin, Barbara C ^c  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

^c STATE UNIVERSITY OF MARINGÁ   (Brazil)

Author keywords

1H, 13C, 15N NMR; Conformations; Fluoroacetoximes; Solvation theory; Theoretical calculation

Indexed keywords

AMINO ACIDS; CARBON; CONFORMATIONS; HYDROGEN; HYDROGEN BONDS; INFRARED RADIATION; MICROWAVES; NITROGEN; NUCLEAR MAGNETIC RESONANCE; PROTEINS; SOLVENTS;

COUPLING CONSTANT; FLUOROACETOXIMES; ISOMERISM; ROTAMER GEOMETRIES; SOLVATION THEORY;

ETHERS;

EID: 0347946802     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.682     Document Type: Article

References (32)

1. McCarty CG. In The Chemistry of the Carbon-Nitrogen Double Bond, Patai S (ed). Wiley: Chichester, chap. 2, 1970.
2. Fry AJ, Reed RG. In The Chemistry of Double Bonded Functional Groups, Supplement A, Patai S (ed.). Wiley: Chichester, chap. 11, 1977.
3. Goda H, Sato M, Ihara H, Hirayama C. Synthesis 1992; 849.
4. (a) CIBA Symposium, Carbon-Fluorine Compounds, Chemistry, Biochemistry and Biological Activities. Association of Scientific Publishers: Amsterdam, 1972;
5. (b) Taylor NF (ed). Fluorinated Carbohydrates, Chemical and Biochemical Aspects. ACS Symposium Series 374. American Chemical Society: Washington, DC, 1988.
6. O'Hagan D, Rzepa HS. Chem. Commun. 1997; 645.
7. Saegebarth E, Krishner LC. J. Chem. Phys. 1970; 52: 3555.
8. Durig JR, Hardin JA, Phan HV, Little TS. Spectrochim. Acta, Part A 1989; 45: 1239.
9. Abraham RJ, Jones AD, Warne MA, Rittner R, Tormena CF. J. Chem. Soc., Perkin Trans. 2 1996; 533.
10. Olivato PR, Ribeiro DS, Rittner R, Hase Y, del Pra D, Bombieri G. Spectrochim. Acta, Part A 1995; 51: 1479.
11. Dal Colle M, Distefano G, Modelli A, Jones D, Guerra M, Olivato PR, Ribeiro DS. J. Phys. Chem. A 1998; 102: 8037.
12. Ribeiro DS, Abraham RJ. Magn. Reson. Chem. 2002; 40: 49.
13. Olivato PR, Ribeiro DS, Zukerman-Schpector J, Bombieri G. Acta Crystallogr., Sect. B 2001; 57: 705.
14. Abraham RJ, Fisher J, Loftus P. Introduction to NMR Spectroscopy. Wiley: New York, 1988.
15. Abraham RJ, Bretschneider E. In Internal Rotation in Molecules, W. J. Orville-Thomas (ed.). Wiley: London, chap. 13, 1974.
16. Frisch MJ, Trucks CW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachavi K, Foresman JB, Ciolowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson BG, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.7. Gaussian: Pittsburgh, PA, 1998.
17. Abraham RJ, Tormena CF, Rittner R. J. Chem. Soc., Perkin Trans. 2 1999; 1663.
18. Tormena CF, Rittner R, Abraham RJ, Basso EA, Pontes RM. J. Chem. Soc., Perkin Trans. 2 2000; 2054.
19. Abraham RJ, Tormena CF, Rittner R. J. Chem. Soc., Perkin Trans. 2 2001; 815.
20. Tormena CF, Rittner R, Abraham RJ. J. Phys. Org. Chem. 2002; 15:211.
21. Tormena CF, Amadeu NS, Rittner R, Abraham RJ. J. Chem. Soc., Perkin Trans. 2 2002; 773.
22. Abraham RJ. Prog. Nucl. Magn. Reson. Spectrosc. 1999; 35: 85.
23. Abraham RJ, Leonard P, Smith TAD, Thomas WA. Magn. Reson. Chem. 1996; 34: 71.
24. Hirota E. J. Chem. Phys. 1970; 42: 2071.
25. Enevoldsen T, Oddershede J, Sauer SPA. Theor. Chem. Acc. 1998; 100: 275.
26. Peralta JE, Barone V, Contreras RH. J. Am. Chem. Soc. 2001 ; 123: 9162.
27. Peralta JE, Barone V, Azua MCR, Contreras RH. Mol. Phys. 2001; 99: 655.
28. Barone V, Peralta JE, Contreras RH. J. Comput. Chem. 2001; 22: 1615.
29. Krivdin LB, Sauer SPA, Peralta JE, Contreras RH. Magn. Reson. Chem. 2002; 40: 187.
30. Freitas MP, Rittner R, Tormena CF, Abraham RJ. J. Phys. Org. Chem. 2001; 14: 317.
31. Contreras RH, Peralta JE. Prog. Nucl. Magn. Reson. Spectrosc. 2000; 37: 321.
32. Braun S, Kalinowski HO, Berger S. 100 and More Basic NMR Experiments. VCH: Weinheim, 1996.