Minimalist Relativistic Force Field: Prediction of Proton-Proton Coupling Constants in 1H NMR Spectra Is Perfected with NBO Hybridization Parameters

Journal of Organic Chemistry

Volumn 80, Issue 10, 2015, Pages 5218-5225

  Kutateladze, Andrei G ^a   Mukhina, Olga A ^a  

^a UNIVERSITY OF DENVER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; HYDROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ACCURATE PREDICTION; CHEMICAL EQUATIONS; MOLECULAR GEOMETRIES; NATURAL PRODUCTS; NON-HYDROGEN ATOMS; PROTON-PROTON COUPLING CONSTANTS; SPIN-SPIN COUPLING CONSTANTS; SYNTHETIC MOLECULES;

COMPLEXATION;

CARBON; HYDROGEN; PROTON;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; GEOMETRY; HYBRIDIZATION; HYDROGEN BOND; MAGNETIC FIELD; MOLECULAR MECHANICS; NATURAL BOND ORBITAL HYBRIDIZATION; PHYSICAL PARAMETERS; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE; SPIN SPIN COUPLING CONSTANT;

EID: 84929590438     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00619     Document Type: Article

References (79)

1. Onak, T.; Jaballas, J.; Barfield, M. J. Am. Chem. Soc. 1999, 121, 2850
2. Scheurer, C.; Bruschweiler, R. J. Am. Chem. Soc. 1999, 121, 8661
3. Del Bene, J. E.; Bartlett, R. J. J. Am. Chem. Soc. 2000, 122, 10480
4. Del Bene, J. E.; Perera, S. A.; Bartlett, R. J. J. Am. Chem. Soc. 2000, 122, 3560
5. Del Bene, J. E.; Perera, S. A.; Bartlett, R. J. J. Phys. Chem. A 2001, 105, 930
6. Diez, E.; Casanueva, J.; San Fabian, J.; Esteban, A. L.; Galache, M. P.; Barone, V.; Peralta, J. E.; Contreras, R. H. Mol. Phys. 2005, 103, 1307
7. Bally, T.; Rablen, P. R. J. Org. Chem. 2011, 76, 4818
8. Kutateladze, A. G.; Mukhina, O. A. J. Org. Chem. 2014, 79, 8397
9. Alabugin, I. V.; Bresch, S.; Gomes, G. P. J. Phys. Org. Chem. 2014, 28, 147
10. Wilkens, S. J.; Westler, W. M.; Markley, J. L.; Weinhold, F. J. Am. Chem. Soc. 2001, 123, 12026
11. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211
12. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066
13. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735
14. National Institute for Advanced Industrial Science and Technology, Japan, http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre-index.cgi.
15. Glendening, E. D.; Badenhoop, K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Landis, C. R.; Weinhold, F. Theoretical Chemistry Institute; University of Wisconsin, Madison, 2013.
16. We suggest that the corrections accounting for these "missing" contributions to SSCCs should correlate with the p-character of the hybrid orbitals (for example, a non-zero contribution from spin-orbit coupling necessarily requires orbital angular momentum). On the contrary, if parametric corrections were needed primarily to refine the dominating contributor, i.e., the Fermi contacts, one would expect these corrections to correlate with the s-character of the hybrid orbitals, not p.
17. Crimmins, M. T.; Pace, J. M.; Nantermet, P. G.; Kim-Meade, A. S.; Thomas, J. B.; Watterson, S. H.; Wagman, A. S. J. Am. Chem. Soc. 2000, 122, 8453
18. Brito, I.; Cueto, M.; Diaz-Marrero, A. R.; Darias, J.; San Martin, A. S. J. Nat. Prod. 2002, 65, 946
19. Okamura, H.; Iwagawa, T.; Nakatani, M. Bull. Chem. Soc. Jpn. 1995, 68, 3465
20. Cobas, J. C.; Constantino-Castillo, V.; Martin-Pastor, M.; del Rio-Portilla, F. Magn. Reson. Chem. 2012, 50, S86
21. Lodewyk, M. W.; Soldi, C.; Jones, P. B.; Olmstead, M. M.; Rita, J.; Shaw, J. T.; Tantillo, D. J. J. Am. Chem. Soc. 2012, 134, 18550
22. Findlay, J. A.; Li, G. Can. J. Chem. 2002, 80, 1697
23. Dong, L.-B.; Gao, X.; Liu, F.; He, J.; Wu, X.-D.; Li, Y.; Zhao, Q.-S. Org. Lett. 2013, 15, 3570
24. Neville, G. A.; Ekiel, I.; Smith, I. C. P. Magn. Reson. Chem. 1987, 25, 31
25. Huang, Z.; Dan, Y.; Huang, Y.; Lin, L.; Li, T.; Ye, W.; Wei, X. J. Nat. Prod. 2004, 67, 2121
26. Mehta, G.; Pallavi, K. Tetrahedron Lett. 2006, 47, 8355
27. Xie, H.-H.; Xu, X.-Y.; Dan, Y.; Wei, X.-Y. Helv. Chim. Acta 2011, 94, 868
28. Kam, T.-S.; Choo, Y.-M. Phytochemistry 2004, 65, 603
29. Ali, A. A.; El Sayed, H. M.; Abdallah, O. M.; Steglich, W. Phytochemistry 1986, 25, 2399
30. Yang, X.-W.; Yang, C.-P.; Jiang, L.-P.; Qin, X.-J.; Liu, Y.-P.; Shen, Q.-S.; Chen, Y.-B.; Luo, X.-D. Org. Lett. 2014, 16, 5808
31. Kimishima, A.; Umihara, H.; Mizoguchi, A.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2014, 16, 6244
32. Suzuki, M.; Daitoh, M.; Vairappan, C. S.; Abe, T.; Masuda, M. J. Nat. Prod. 2001, 64, 597
33. Reekie, T. A.; Banwell, M. G.; Willis, A. C. J. Org. Chem. 2012, 77, 10773
34. Das, D.; Kant, R.; Chakraborty, T. K. Org. Lett. 2014, 16, 2618
35. Marrero, J.; Rodriguez, A. D.; Baran, P.; Raptis, R. G.; Sanchez, J. A.; Ortega-Barria, E.; Capson, T. L. Org. Lett. 2004, 6, 1661
36. Casero, C. N.; Oberti, J. C.; Orozco, C. I.; Cárdenas, A.; Brito, I.; Barboza, G. E.; Nicotra, V. E. Phytochemistry 2015, 110, 83
37. Deng, C.; Huang, C.; Wu, Q.; Pang, J.; Lin, Y. Nat. Prod. Res. 2013, 27, 1882
38. He, Y.; Peng, J.; Hamann, M. T.; West, L. M. J. Nat. Prod. 2014, 77, 2138
39. Zhang, C.; Liu, J.; Du, Y. Tetrahedron Lett. 2013, 54, 3278
40. Oh, D.-C.; Williams, P. G.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Org. Lett. 2006, 8, 1021
41. Miyake, K.; Tezuka, Y.; Awale, S.; Li, F.; Kadota, S. J. Nat. Prod. 2009, 72, 2135
42. Low, Y. Y.; Hong, F.-J.; Lim, K.-H.; Thomas, N.-F.; Kam, T.-S. J. Nat. Prod. 2014, 77, 327
43. Dong, M.; Cong, B.; Yu, S.-H.; Sauriol, F.; Huo, C.-H.; Shi, Q.-W.; Gu, Y.-C.; Zamir, L. O.; Kiyota, H. Org. Lett. 2008, 10, 701
44. Fu, C.; Zhang, Y.; Xuan, J.; Zhu, C.; Wang, B.; Ding, H. Org. Lett. 2014, 16, 3376
45. Zhao, J.-X.; Liu, C.-P.; Qi, W.-Y.; Han, M.-L.; Han, Y.-S.; Wainberg, M. A.; Yue, J.-M. J. Nat. Prod. 2014, 77, 2224
46. Li, J.-Y.; Zhao, B.-X.; Zhang, W.; Li, C.; Huang, X.-J.; Wang, Y.; Sun, P.-H.; Ye, W.-C.; Chen, W.-M. Tetrahedron 2012, 68, 3972
47. Cleary, L.; Pitzen, J.; Brailsford, J. A.; Shea, K. J. Org. Lett. 2014, 16, 4460
48. Lakornwong, W.; Kanokmedhakul, K.; Kanokmedhakul, S.; Kongsaeree, P.; Prabpai, S.; Sibounnavong, P.; Soytong, K. J. Nat. Prod. 2014, 77, 1545
49. Finn, P. B.; Kulyk, S.; Sieburth, S. McN. Tetrahedron Lett. 2015, 10.1016/j.tetlet.2015.01.145
50. Ng, F. W.; Lin, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 9812
51. Jansen, R.; Sood, S.; Mohr, K. I.; Kunze, B.; Irschik, H.; Stadler, M.; Müller, R. J. Nat. Prod. 2014, 77, 2545
52. Chen, S.; Zhang, Y.; Niu, S.; Liu, X.; Che, Y. J. Nat. Prod. 2014, 77, 1513
53. Luo, Q.; Tian, L.; Di, L.; Yan, Y.-M.; Wei, X.-Y.; Wang, X.-F.; Cheng, Y.-X. Org. Lett. 2015, 17, 1565
54. Ziegler, F. E.; Metcalf, C. A., III; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1993, 115, 2581
55. Porco, J. A.Jr.; Su, S.; Lei, X.; Bardhan, S.; Rychnovsky, S. D. Angew. Chem. 2006, 118, 5922
56. Yang, X.-W.; Peng, K.; Liu, Z.; Zhang, G.-Y.; Li, J.; Wang, N.; Steinmetz, A.; Liu, Y. J. Nat. Prod. 2013, 76, 2360
57. Bai, R.; Zhang, C.-C.; Yin, X.; Wei, J.; Gao, J.-M. J. Nat. Prod. 2015, 78, 783
58. Hajicek, J.; Taimr, J.; Budesinsky, M. Tetrahedron Lett. 1998, 39, 505
59. Kitabayashi, Y.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2014, 16, 2862
60. Umehara, A.; Ueda, H.; Tokuyama, H. Org. Lett. 2014, 16, 2526
61. Chen, H.-J.; Wu, Y. Org. Lett. 2015, 17, 592
62. Hoshi, M.; Kaneko, O.; Nakajima, M.; Arai, S.; Nishida, A. Org. Lett. 2014, 16, 768
63. Carlsen, P. N.; Mann, T. J.; Hoveyda, A. H.; Frontier, A. J. Angew. Chem. 2014, 53, 9334
64. Lu, P.; Gu, Z.; Zakarian, A. J. Am. Chem. Soc. 2013, 135, 14552
65. Chen, S.; Ren, F.; Niu, S.; Liu, X.; Che, Y. J. Nat. Prod. 2014, 77, 9
66. Calandra, N. A.; King, S. M.; Herzon, S. B. J. Org. Chem. 2013, 78, 10031
67. Homs, A.; Muratore, M. E.; Echavarren, A. M. Org. Lett. 2015, 17, 461
68. Sim, D. S.-Y.; Chong, K.-W.; Nge, C.-E.; Low, Y.-Y.; Sim, K.-S.; Kam, T.-S. J. Nat. Prod. 2014, 77, 2504
69. Kam, T.-S.; Sim, K.-M.; Lim, T.-M. Tetrahedron Lett. 1999, 40, 5409
70. Raju, R.; Piggott, A. M.; Huang, X.; Capon, R. J. Org. Lett. 2011, 13, 2770
71. Note that proton 1″a in Capon's paper is listed as 2.79 ppm dd 11.0, 3.7 Hz, with 11.0 being a typo.
72. Wang, H.; Reisman, S. E. Angew. Chem., Int. Ed. 2014, 53, 6206
73. Yin, G.-P.; Li, L.-C.; Zhang, Q.-Z.; An, Y.-W.; Zhu, J.-J.; Wang, Z.-M.; Chou, G.-X.; Wang, Z.-T. J. Nat. Prod. 2014, 77, 2161
74. Peese, K. M.; Gin, D. Y. Chem.-Eur. J. 2008, 14, 1654
75. Daengrot, C.; Rukachaisirikul, V.; Tansakul, C.; Thongpanchang, T.; Phongpaichit, S.; Bowornwiriyapan, K.; Sakayaroj, J. J. Nat. Prod. 2015, 78, 615
76. It is important to note that in the DU8 approach the actual computations of Fermi contacts take less than a third of the total computational time. Nearly two-thirds of computational time is used for computing the isotropic components of the magnetic shielding tensors at the GIAO, mPW1PW91/6-311+G(d,p) level of theory to obtain chemical shifts, with the reminder of the time spent for geometry optimization. Without chemical shifts, accurate SSCCs for penicilleremophilane B are obtained in less than 6 min of computational (wall) time.
77. Hsieh, T.-J.; Chen, C.-Y.; Kuo, R.-Y.; Chang, F.-R.; Wu, Y.-C. J. Nat. Prod. 1999, 62, 1192
78. Ku, A. F.; Cuny, G. D. Org. Lett. 2015, 17, 1134
79. Zhong, X.; Li, Y.; Zhang, J.; Han, F.-S. Org. Lett. 2015, 17, 720