Simulation of 2D 1H homo- and 1H-13C heteronuclear NMR spectra of organic molecules by DFT calculations of spin-spin coupling constants and 1H and 13C-chemical shifts

Tetrahedron

Volumn 59, Issue 48, 2003, Pages 9555-9562

  Bassarello, Carla ^a   Cimino, Paola ^a   Gomez Paloma, Luigi ^a   Riccio, Raffaele ^a   Bifulco, Giuseppe ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

13C NMR; 1H NMR; DFT calculations; GIAO; J couplings; Natural products; Structure elucidation

Indexed keywords

2 NORBORNANECARBAMIC ACID; AFLATOXIN B1; ALKENE DERIVATIVE; BENZOFURANOEREMOPHIL 1 ENE; ESTER DERIVATIVE; GRISEOFULVIN; MAGNOLIALIDE; ORGANIC COMPOUND; UNCLASSIFIED DRUG; YOHIMBAN DERIVATIVE;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; GEOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PREDICTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SIMULATION;

HOMO;

EID: 0242289574     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.001     Document Type: Article

References (31)

1. de Dios A.C. J. Prog. Nucl. Magn. Reson. Spectrosc. 29:1996;229-278.
2. Helgaker T., Jaszunski M., Ruud K. Chem. Rev. 99:1999;293-352.
3. Wolinski K., Hinton J.F., Pulay P. J. Am. Chem. Soc. 112:1990;8251-8260.
4. Barone G., Gomez-Paloma L., Duca D., Silvestri A., Riccio R., Bifulco G. Chem. Eur. J. 8:2002;3233-3239.
5. Barone G., Duca D., Silvestri A., Gomez-Paloma L., Riccio R., Bifulco G. Chem. Eur. J. 8:2002;3240-3245.
6. Taehtinen P., Bagno A., Klika K.D., Pihlaja K. J. Am. Chem. Soc. 125:2003;4609-4618.
7. Cloran F., Carmichael I., Serianni A.S. J. Am. Chem. Soc. 123:2001;4781-4791.
8. Bagno A. Chem. Eur. J. 7:2001;1652-1661.
9. Cimino, P.; Gomez-Paloma, L.; Duca, D.; Riccio, R.; Bifulco, G. J. Mol. Struct. (Theochem), submitted for publication.
10. Mao H., Deng Z., Wang F., Harris T.M., Stone M.P. Biochemistry. 37:1998;4374-4387.
11. Liu Z., Chen H., Jia Z., Dalley N.K., Hou X., Li D., Owen N.L., Grant D.M. Phytochemistry. 40:1995;1191-1192.
12. Kisiel W., Zielińska K. Phytochemistry. 57:2001;523-527.
13. Aubé J., Ghosh S., Tanol M. J. Am. Chem. Soc. 116:1994;9009-9018.
14. Arison, B. H.; Wendler, N. L.; Taub, D.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Trenner, N. R. Contribution from the Merck Sharp & Dohme Research Laboratories, Merck & Co., Inc.: Rahway, NJ, 5 March, 1963.
15. Adamo C., Barone V. J. Chem. Phys. 108:1998;664-675.
16. Becke A.D. J. Chem. Phys. 98:1993;5648-5652.
17. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T., Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03W, Revision 6.0; Gaussian, Inc., Pittsburgh PA, 2003.
18. Aue W.P., Bartholdi E., Ernst R.R. J. Chem. Phys. 64:1976;2229-2246.
19. Abragam A. The Principles of Nuclear Magnetism. 1961;University, Oxford.
20. Slichter C.P. Principles of Magnetic Resonance. 1978;Springer, Berlin.
21. Bloch F. Phys. Rev. 105:1957;1206-1222.
22. Bruker Analytic GmbH. NMR-Sim software Manual, version 3.0, 2001.
23. Bax A., Summers M.F. J. Am. Chem. Soc. 108:1986;2093-2094.
24. Burum D.P., Ernst R.R. J. Magn. Reson. 39:1980;163-168.
25. Uhrín D., Batta G., Hruby V.J., Barlow P.N., Kövér K.E. J. Magn. Reson. 130:1998;155-161.
26. Boyd J., Soffe N., John B., Plant D., Hurd R. J. Magn. Reson. 98:1992;660-664.
27. Davis A.L., Keeler J., Laue E.D., Moskau D. J. Magn. Reson. 98:1992;207-216.
28. Dauber-Osguthorpe P., Roberts V.A., Osguthorpe D.J., Wolff J., Genest M., Hagler A.T. Proteins: Struct. Funct. Genet. 4:1988;31-47.
29. Accelrys Inc. (US, U.K.) 9685 Scranton Rd, San Diego, CA, 92121-3752.
30. Ditchfield R. Mol. Phys. 27:1974;789-807.
31. Rohlfing C.M., Allen L.C., Ditchfield R. Chem. Phys. 8:1984;9-15.