A multi-standard approach for GIAO 13C NMR calculations

Journal of Organic Chemistry

Volumn 74, Issue 19, 2009, Pages 7254-7260

  Sarotti, Ariel M ^a   Pellegrinet, Silvina C ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

ACCURACY AND PRECISION; BASIS SETS; CARBON ATOMS; COMPUTATIONAL COSTS; MULTI-STANDARD; NMR CHEMICAL SHIFTS; REFERENCE STANDARD;

BENZENE; CHEMICAL SHIFT; METHANOL; NUCLEAR MAGNETIC RESONANCE; ORGANIC COMPOUNDS;

STANDARDS;

BENZENE; METHANOL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; MATHEMATICAL MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY;

CARBON ISOTOPES; COMPUTER SIMULATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; QUANTUM THEORY; REFERENCE STANDARDS;

EID: 70349462963     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901234h     Document Type: Article

References (67)

1. Nicolaou, K. C.; Snyder, S. A. Angew. Chem., Int. Ed. 2005, 44, 1012-1044.
2. Helgaker, T.; Jaszunski, M.; Ruud, K. Chem. Rev. 1999, 99, 293-352.
3. Bifulco, G.; Dambruoso, P.; Gomez-Paloma, L.; Riccio, R. Chem. Rev. 2007, 107, 3744-3779.
4. Barone, G.; Gomez-Paloma, L.; Duca, D.; Silvestri, A.; Riccio, R.; Bifulco, G. Chem.;Eur. J. 2002, 8, 3233-3239.
5. Barone, G.; Duca, D.; Silvestri, A; Gomez-Paloma, L.; Riccio, R.; Bifulco, G. Chem.;Eur. J. 2002, 8, 3240-3245.
6. For recent references, see: (a) Smith, S. G.; Goodman, J. M. J. Org. Chem. 2009, 74, 4597-4607.
7. (b) Mendoza-Espinoza, J. A.; López-Vallejo, F.; Fragoso-Serrano, M.; Pereda-Miranda, R.; Cerda-García-Rojas, C. M. J. Nat. Prod. 2009, 72, 700-708.
8. (c) Wang, B.; Dossey, A. T.; Walse, S. S.; Edison, A. S.; Merz, K. M. J. Nat. Prod. 2009, 72, 709-713.
9. (d) Smith, S. G.; Paton, R. S.; Burton, J. W.; Goodman, J. M. J. Org. Chem. 2008, 73, 4053-4062.
10. (e) Koskowich, S. M.; Johnson, W. C.; Paley, R. S.; Rablen, P. R. J. Org. Chem. 2008, 73, 3492-3496.
11. (f) Hu, G.; Liu, K.; Williams, L. J. Org. Lett. 2008, 10, 5493-5496.
12. (g) Fattorusso, E.; Luciano, P.; Romano, A.; Taglialatela-Scafati, O.; Appendino, G.; Borriello, M.; Fattorusso, C. J. Nat. Prod. 2008, 71, 1988-1992.
13. (h) Belostotskii, A. M. J. Org. Chem. 2008, 73, 5723-5731.
14. (i) Allouche, A. R.; Graveron-Demilly, D.; Fauvelle, F.; Aubert-Frecon, M. Chem. Phys. Lett. 2008, 466, 219-222.
15. (j) White, K. N.; Amagata, T.; Oliver, A. G.; Tenney, K.; Wenzel, P. J.; Crews, P. J. Org. Chem. 2008, 73, 8719-8722.
16. (k) Braddock, D. C.; Rzepa, H. S. J. Nat. Prod. 2008, 71, 728-730.
17. (l) Griesbeck, A. G.; Blunk, D.; El-Idreesy, T. T.; Raabe, A. Angew. Chem., Int. Ed. 2007, 46, 8883-8886.
18. (m) Bassarello, C.; Bifulco, G.; Montoro, P.; Skhirtladze, A.; Kemertelidze, E.; Pizza, C.; Piacente, S. Tetrahedron 2007, 63, 148-154.
19. (n) Pu, J. X.; Huang, S. X.; Ren, J.; Xiao, W. L.; Li, L. M.; Li, R. T.; Li, L. B.; Liao, T. G.; Lou, L. G.; Zhu, H. J.; Sun, H. D. J. Nat. Prod. 2007, 70, 1706-1711.
20. (o) Fattorusso, C.; Stendardo, E.; Appendino, G.; Fattorusso, E.; Luciano, P.; Romano, A.; Taglialatela-Scafati, O. Org. Lett. 2007, 9, 2377-2380.
21. (p) Nicolaou, K. C.; Frederick, M. O. Angew. Chem., Int. Ed. 2007, 46, 5278-5282.
22. (q) Rasul, G.; Olah, G. A.; Prakash, G. K. S. J. Phys. Chem. A 2006, 110, 7197-7201.
23. (r) Rychnovsky, S. D. Org. Lett. 2006, 8, 2895-2898.
24. (s) Bifulco, G.; Gomez-Paloma, L.; Riccio, R.; Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2005, 7, 5757-5760.
25. (t) Aiello, A.; Fattorusso, E.; Luciano, P.; Mangioni, A.; Menna, M. Eur. J. Org. Chem. 2005, 23, 5024-5030.
26. (u) Sebag, A. B.; Forsyth, D. A.; Plante, M. A. J. Org. Chem. 2001, 66, 7967-7973.
27. (v) Sebag, A. B.; Friel, C. J.; Hanson, R. N.; Forsyth, D. A. J. Org. Chem. 2000, 65, 7902-7912.
28. Forsyth, D. A.; Sebag, A. B. J. Am. Chem. Soc. 1997, 119, 9483-9494.
29. Aliev, A. E.; Courtier-Murias, D.; Zhou, S. J. Mol. Struct. (THEOCHEM) 2009, 893, 1-5.
30. Rablen, P. R.; Pearlman, S. A.; Finkbiner, J. J. Phys. Chem. A 1999, 103, 7357-7363.
31. Jain, R.; Bally, T.; Rablen, P. R. J. Org. Chem. 2009, 74, 4017-4023.
32. (a) Ditchfield, R. J. Chem. Phys. 1972, 56, 5688-5691.
33. (b) Ditchfield, R. Mol. Phys. 1974, 27, 789-807.
34. (c) Rohlfing, C. M.; Allen, L. C.; Ditchfield, R. Chem. Phys. 1984, 87, 9-15.
35. (d) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
36. Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frish, M. J. J. Chem. Phys. 1996, 104, 5497-5509.
37. Giesen, D. J.; Zumbylyadis, N. Phys. Chem. Chem. Phys. 2002, 4, 5498-5507.
38. Cimino, P.; Gomez-Paloma, L.; Duca, D.; Riccio, R.; Bifulco, G. Magn. Reson. Chem. 2004, 42, S26-S33.
39. Tormena, C. F.; da Silva, G. V. J. Chem. Phys. Lett. 2004, 398, 466-470.
40. Bagno, A.; Rastrelli, F.; Saielli, G. Chem. - Eur. J. 2006, 12, 5514-5525.
41. Wu, Z.; Zhang, Y.; Xu, X.; Yan, Y. J. Comput. Chem. 2007, 28, 2431-2442.
42. Wiitala, K. W.; Hoyle, T. R.; Cramer, C. J. J. Chem. Theory Comput. 2006, 2, 1085-1092.
43. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2008, 112, 6794-6799.
44. Baldridge, K. K.; Siegel, J. S. J. Phys. Chem. A 1999, 103, 4038-4042.
45. Schuler, R. H.; Albarran, G.; Zajicek, J.; George, M. V.; Fessenden, R. W.; Carmichael, I. J. Phys. Chem. A 2002, 106, 12178-12183.
46. (a) Wipf, P.; Kerekes, A. J. Nat. Prod. 2003, 66, 716-718.
47. (b) Timmons, C.; Wipf, P. J. Org. Chem. 2008, 73, 9168-9170.
48. Gottlieb, H. E.; Kotylar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512-7515.
49. (a) Breitmaier, E. Structure Elucidation by NMR in Organic Chemistry; John Wiley & Sons: England, 2002.
50. (b) Sarotti, A. M.; Spanevello, R. A.; Suárez, A. G. Tetrahedron 2007, 63, 241-251.
51. (c) Lagorio, S. H.; Bianchi, D. A.; Sutich, E. G.; Kaufman, T. S. Eur. J. Med. Chem. 2006, 41, 1333-1338.
52. (d) http://riodb01.ibase.aist.go.jp/sdbs/.
53. It is well-known that magnetic shielding values frequently show a strong conformational dependence. If a molecule has more than one significantly populated conformer, then a prediction of chemical shifts requires a separate calculation for each conformer, followed by the calculation of the Boltzmann-weighted average. The assumption that neglecting the contributions of other low-energy conformers do not affect the results might be questionable. However, we found that for the chosen compounds the chemical shifts calculated using the global minima and all significant conformers showed no significant variations. This issue is discussed in more detail in the Supporting Information.
54. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
55. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
56. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
57. (d) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
58. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
59. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
60. Throughout this study, we will use this term. In order to avoid misinterpretation, we aim to clarify that the type of hybridization refers only to the carbons of compounds shown in Figure 1 and not to the carbons of the reference standards.
61. Since the functional mPW1PW91 gave slightly lower MAD and RMS errors than B3LYP, the first was selected for the GIAO NMR calculations.
62. Morgan, E. Chemometrics: Experimental Design; Wiley: New York, 1995.
63. For detailed discussion on this issue, see the Supporting Information.
64. 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 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
65. Hyperchem Professional Release 7.52; Hypercube, Inc., 2005.
66. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127-8134.
67. For a review on continuum solvation models, see: Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093.