The shielding effect of fluoroaromatic rings in NMR

Journal of Fluorine Chemistry

Volumn 156, Issue , 2013, Pages 1-4

  Korenaga, Toshinobu ^a   Kobayashi, Fuminao ^a   Nomura, Kenji ^a   Sakai, Takashi ^a   Shimada, Kazuaki ^a  

^a IWATE UNIVERSITY   (Japan)

Author keywords

DFT calculations; Fluoroaromatics; Phosphine; Quadrupole moment; Shielding effect

Indexed keywords

EID: 84883690899     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2013.08.004     Document Type: Article

References (30)

1. J.I. Wu, F.G. Puhlhofer, P.R. Schleyer, R. Puchta, B. Kiran, M. Mauksch, N.J.R. van Eikema Hommes, I. Alkorta, and J. Elguero J. Phys. Chem. A 113 2009 6789 6794
2. S.N. Steinmann, D.F. Jana, J.I.-C. Wu, P.v.R. Schleyer, Y. Mo, and C. Corminboeuf Angew. Chem. Int. Ed. 48 2009 9828 9833
3. P.W. Fowler, and E. Steiner J. Phys. Chem. A 101 1997 1409 1413
4. Review K.M. Błażewska, and T. Gajda Tetrahedron: Asymmetry 20 2009 1337 1361
5. Q. Ma, M. Ma, H. Tian, X. Ye, H. Xiao, L. Chen, and X. Lei Org. Lett. 14 2012 5813 5815 (recent examples)
6. R.N. Rao, B. Ramachandra, and K. Santhakumar Chirality 24 2012 339 344
7. L. Liu, M. Ye, X. Hu, X. Yu, L. Zhang, and X. Lei Tetrahedron: Asymmetry 22 2011 1667 1671
8. S. Bozkurt, M. Durmaz, H.N. Naziroglu, M. Yilmaz, and A. Sirit Tetrahedron: Asymmetry 22 2011 541 549
9. S. Kim, and K. Choi Euro. J. Org. Chem. 2011 4747 4750
10. K. Tanaka, Y. Nakai, and H. Takahashi Tetrahedron: Asymmetry 22 2011 178 184
11. 6
12. I. Alkorta, I. Rozas, M.L. Jimeno, and J. Elguero Struct. Chem. 12 2001 459 464
13. P.v.R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, and N.J.R. van Eikema Hommes J. Am. Chem. Soc. 118 1996 6317 6318
14. Review Z. Chen, C.S. Wannere, C. Corminboeuf, R. Puchta, and P.v.R. Schleyer Chem. Rev. 105 2005 3842 3888
15. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
16. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
17. M.J. Frisch, J.A. Pople, and J.S. Binkley J. Chem. Phys. 80 1984 3265 3269
18. T. Clark, J. Chandrasekhar, G.W. Spitznagel, and P.V.R. Schleyer J. Comp. Chem. 4 1983 294 301
19. Gaussian 03, Revision, E., 01 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, and J.A. Pople Gaussian, Inc., Wallingford, CT 2004
20. R. Ditchfield Chem. Phys. Lett. 15 1972 203 206
21. P.v.R. Schleyer, M. Manoharan, Z.-X. Wang, B. Kiran, H. Jiao, R. Puchta, and N.J.R. van Eikema Hommes Org. Lett. 3 2001 2465 2468
22. T. Okazaki, and K.K. Laali Org. Biomol. Chem. 4 2006 3085 3095
23. 6 is 3.20 Å J.P. Gallivan, and D.A. Dougherty Org. Lett. 1 1999 103 105
24. 6 centroid-methyl anion distance is 3.36 Å I. Alkorta, I. Rozas, and J. Elguero J. Am. Chem. Soc. 124 2002 8593 8598
25. 6 is 3.4 Å E.A. Meyer, R.K. Castellano, and F. Diederich Angew. Chem. Int. Ed. 42 2003 1210 1250
26. The quadrupole moments tensor (Θzz) for the guest compounds were calculated at the B3LYP/6-311+g(d,p) using Gaussian 03 by following the procedure described in the paper by K. Tsang, M. Ng, N.L. Ma, and C.W. Tsang Rapid Commun. Mass. Spectrom. 12 1998 1679 1684
27. H. Stamm, and H. Jaeckel J. Am. Chem. Soc. 111 1989 6544 6550
28. T. Korenaga, K. Osaki, R. Maenishi, and T. Sakai Org. Lett. 11 2009 2325 2328
29. T. Korenaga, A. Ko, K. Uotani, Y. Tanaka, and T. Sakai Angew. Chem. Int. Ed. 50 2011 10703 10707
30. The structural optimization at the B3LYP/6-31G(g) level can give the similar result to that at the B3LYP/6-311+G(d,p) level to estimate correlation between calculated shielding tensors and observed chemical shifts N.J.R. van Eikema Hommes, and T. Clark J. Mol. Model. 11 2005 175 185