Structure determination of slowly exchanging conformers in solution using high-resolution NMR, computational modeling and DFT- GIAO chemical shielding: Application to an erythronolide a derivative

Magnetic Resonance in Chemistry

Volumn 47, Issue 11, 2009, Pages 909-916

  Muri, Dieter ^a   Corminboeuf, Clémence ^b   Carreira, Erick M ^a   Jeannerat, Damien ^c  

^a ETH ZURICH   (Switzerland)

^b INSTITUTE OF CHEMICAL SCIENCES AND ENGINEERING   (Switzerland)

^c UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Structure determination; conformers; NMR; erythronolide; synthesis; spectral aliasing

Indexed keywords

COMPUTATION THEORY; SHIELDING;

CHEMICAL SHIELDING; CONFORMER;; DENSITY-FUNCTIONAL-THEORY; ERYTHRONOLIDE;; HIGH RESOLUTION; NMR;; SPECTRAL ALIASING; STRUCTURE DETERMINATION; STRUCTURE DETERMINATION;; SYNTHESIS;;

DENSITY FUNCTIONAL THEORY;

EID: 70350026328     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.2476     Document Type: Article

References (28)

1. T. D.W. Claridge, High Resolution NMR Techniques in Organic Chemistry, vol.19, Pergamon Press: Oxford, 1999.
2. D. Jeannerat, D. Ronan, Y. Haudry, A. Pinto, J. P. Saulnier, S. Matile, Helv. Chim. Acta. 2004,87, 2190.
3. E. KupŠe,T.Nishida, R.Freeman, Prog. Nucl. Magn. Reson. Spectrosc. 2003,42,95.
4. W.F.Reynolds, M.Yu, R.G.Enriquez, I.Leon, Magn. Reson. Chem. 1997,35,505.
5. J. A. Jones, P. J. Hore, J. Magn. Reson. 1991,92,276.
6. D. Jeannerat, Magn. Reson. Chem. 2003,47,3.
7. D. Jeannerat, J. Magn. Reson. 2007, 786,112.
8. B. Vitorge, D. Jeannerat, Anal. Chem. 2006,78, 7601.
9. D. Muri, N. Lohse-Fraefel, E. M. Carreira, Angew. Chem. Int. Ed. 2005, 44, 4036.
10. L. Lerner, A. Bax, J. Magn. Reson. 1986,69, 375.
11. P. Nolis, T. Parella, J. Magn. Reson. 2005, 776,15.
12. R. Wagner, S.Berger, J. Magn. Reson. 1997,35, 199.
13. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH: Weinheim, 2001.
14. B. Luy, K. Kobzar, S. Knr, J. Furrer, D. Heckmann, H. Kessler, J. Am. Chem. Soc. 2005, 727,6459.
15. C. M. Thiele, J. Org. Chem. 2004,69, 7403.
16. M. Kaupp, M. Buhl, V.G. Malkin, Calculation of NMR and EPR parameters, Wiley-VCH Verlag GmbH: Weinheim, 2004.
17. F. London, J. Phys. Radium. 1937,8, 397.
18. R. Ditchfield, Mol. Phys. 1974,27, 789.
19. K. Wolinski, J. F.Hinton, P. Pulay, J.Am. Chem.Soc. 1990, 7 72,8251.
20. J. Gauss, J. F. Stanton, Adv. Chem. Phys. 20 02, 723,355.
21. R.Wasylishen,T.Schaefer,Can.J.Chem. 1973,57,961.
22. HyperChem HyperChem professional release 7.2. 2004.
23. N.L.Allinger, J. Am. Chem.Soc. 1977,99,8127.
24. P.J.Stephens, F.J.Devlin, C. F. Chabalowski, M.J. Frisch, J. Phys. Chem. 1994, 98, 11623.
25. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B.Mennucci, M.Cossi, G.Scalmani, N.Rega, G.A.Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y.Honda, O. Kitao, H.Nakai, M. Klene, X.Li, J.E.Knox, H. P. Hratchian, J.B.Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P.Salvador, J.J.Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K.Raghavachari, J. B. Foresman, J.V.Ortiz, Q.Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J.A.Pople,Gaussian,Inc.,Wallingford CT,2004.
26. A.D.Becke,Phys.Rev.A.1988,38,3098.
27. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B. 1988,37, 785.
28. A. M. Nilius, Z. Ma, Curr. Opin. Pharmacol. 2002,2,493.