Visualization and quantification of the anisotropic effect of C=C double bonds on 1H NMR spectra of highly congested hydrocarbons-indirect estimates of steric strain

Journal of Physical Chemistry A

Volumn 112, Issue 22, 2008, Pages 4989-4995

  Kleinpeter, Erich ^a   Koch, Andreas ^a   Seidl, Peter R ^b  

^a UNIVERSITY OF POTSDAM   (Germany)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ANISOTROPY; HYDROCARBONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS;

1H-NMR SPECTRA; ANISOTROPIC EFFECTS; C-C DOUBLE BONDS; DOUBLE BONDS; NMR SHIELDING; NUCLEUS INDEPENDENT CHEMICAL SHIFT; SPATIAL EFFECTS; STERIC STRAINS;

CHEMICAL BONDS;

EID: 53349118353     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp801063t     Document Type: Article

References (62)

1. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; von Ragué Schleyer, P. Chem. Rev. 2005, 105, 3842.
2. von Ragué Schleyer, P.; Manoharan, M.; Wang, Z. X.; Kiran, B.; Jiao, Y.; Puchta, R.; v. E.; Hommes, N. J. R. Org. Lett. 2001, 3, 2465.
3. Klod, S.; Kleinpeter, E. J. Chan. Soc., Perkin Trans. 2 2001, 1893.
4. (a) Kleinpeter, E.; Klod, S.; Koch, A. J. Mol. Struct. (THEOCHEM) 2007, 811, 45.
5. (b) Kleinpeter, E.; Holzberger, A.; Wacker, Ph. J. Org. Chan. 2008, 73, 56.
6. (a) Kleinpeter, E.; Klod, S.; Koch, A. J. Org. Chem. 2008, 73, 1498.
7. (b) Kleinpeter, E.; Koch, A. J. Mol. Struct (THEOCHEM) 2008, 851, 313.
8. Toth, C.; Kovacs, J.; Levai, A.; Koch, A.; Kleinpeter, E. Magn. Reson. Chem. 2001, 39, 251.
9. Kleinpeter, E.; Holzberger, A. Tetrahedron 2001, 57, 6941.
10. Germer, A.; Klod, S.; Peter, M. G.; Kleinpeter, E. J. Mol. Model. 2002, 8, 231.
11. Klod, S.; Koch, A.; Kleinpeter, E. J. Chem. Soc., Perkin Trans. 2 2002, 1506.
12. Kovacs, J.; Toth, G.; Simon, A.; Levai, A.; Koch, A.; Kleinpeter, E. Magn. Reson. Chem. 2003, 41, 193.
13. Szatmari, I.; Martinek, A. T.; Lazar, L.; Koch, A.; Kleinpeter, E.; Fülöp, F. Ann. West Univ. Timisoara, Ser. Chem. 2003, 12, 175.
14. Kleinpeter, E.; Klod, S.; Rudorf, W.-D. J. Org. Chem. 2004, 69, 4317.
15. Miklos, F.; Kanizsai, I.; Thomas, St.; Kleinpeter, E.; Silianpää, R.; Stajer, G. Heterocycles 2004, 63, 63.
16. Kleinpeter, E.; Klod, S. J. Am. Chem. Soc. 2004, 126, 2231.
17. Martinek, A.; Lazar, L.; Koch, A.; Kleinpeter, E.; Neuvonen, K.; Fülöp, F. J. Org. Chem. 2004, 69, 3645.
18. Kleinpeter, E.; Klod, S. J. Mol. Struct. 2004, 704, 79.
19. Hausmann, J.; Käss, St.; Klod, S.; Kleinpeter, E. Eur. J. Inorg. Chem. 2004, 4402.
20. Ryppa, C.; Senge, M. O.; Hatscher, S. S.; Wacker, Ph.; Kleinpeter, E.; Schilde, U.; Wiehe, A. Chem. Eur. J. 2005, 11, 3427.
21. Kleinpeter, E.; Schulenburg, A.; Zug, I.; Hartmann, H. J. Org. Chem. 2005, 70, 6592.
22. Kleinpeter, E.; Schulenburg, A. J. Org. Chem. 2006, 71, 3869.
23. Alkorta, I.; Elguero, J. New. J. Chem. 1998, 381.
24. (a) Martin, N. H.; Allen, N. W., III; Moore, K. D.; Vo, L. J. Mol. Struct. (THEOCHEM) 1998, 454, 161.
25. (b) Martin, N. H.; Allen, N. W., III; Moore, J. C. J. Mol. Graph Model 2000, 18, 242.
26. (c) Martin, N. H.; Allen, N. W., III; Minga, E. K.; Ingrassia, S. T.; Brown, J. Struct. Chem. 1998, 9, 403.
27. (d) MartinN. H. AllenN. W. MingaE. K. IngrassiaS. T. BrownJ. D. Proceeding of the American Chemical Society Symposium on Modeling NMR Chemical Shifts: Gaining insight into Structure and Environment; American Chemical Society: Washington, DC, 1999.
28. (e) Martin, N. H.; Allen, N. W., III; Minga, E. K.; Ingrassia, S. T.; Brown, J. D. Struct. Chem. 1999, 10, 375.
29. (f) Martin, N. H.; Allen, N. W., III; Ingrassia, S. T.; Brown, J. D.; Minga, E. K. J. Mol. Graph. Model. 2000, 18, 1.
30. (g) Martin, N. H.; Nance, K. H. J. Mol. Graph. Model 2002, 21, 51.
31. (h) Martin, N. H.; Allen, N. W., III; Brown, J. D.; Kniec, D. M., Jr.; Vo, L. J. Mol. Graph. Model 2003, 22, 127.
32. (i) Martin, N. H.; Loveless, D. M.; Wade, D. G J. Mol. Graph. Model. 2004, 23, 285.
33. Marchand, A. P.; Marchand, N. W. Tetrahedron Lett. 1971, 1365.
34. Abraham, R. J.; Fisher, J. Magn. Reson. Chem. 1985, 23, 856.
35. Fisher, J.; Gradwell, M. J. Magn. Reson. Chem. 1992, 30, 338.
36. Moen, R. V.; Makowski, H. S. Analyt. Chem. 1971, 43, 1629.
37. Mantzaris, J.; Weissberger, E. Tetrahedron Lett. 1972, 2815.
38. Böhm, M. C.; Carr, R. V. C.; Gleiter, R.; Paquette, L. A. J. Am. Chem. Soc. 1980, 102, 7218.
39. Seidl, P. R.; Leal, K. Z.; Costa, V. E. U.; Mollmann, M. E. S. Magn. Reson. Chem. 1993, 31, 246. Mollmann, M. E. S. DC Thesis, UFRGS, Porto Alegre, 1992.
40. Seidl, P. R.; Leal, K. Z.; Costa, V. E. U.; Mollmann, M. E. S. Magn. Reson. Chem. 1998, 36, 261.
41. Stille, J. K.; Witherell, D. R. J. Am. Chem. Soc. 1964, 86, 2188.
42. Pihlaja, K.; Kleinpeter, E. In Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis; VCH Publishers, Inc.: New York, 1994.
43. Winstein, S.; Carter, P.; Anet, F. A. L.; Bourn, A. J. R. J. Am. Chem. Soc. 1965, 87, 5247.
44. Marchand, A. P. Sterechemical Applications of NMR Studies in Rigid Bicyclic Systems; Verlag Chemie: Deerfield Beach, CA, 1982; 15-19.
45. Günther, H. NMR Spektroskopie, 3rd; Georg Thieme Verlag: Stuttgart, 1992.
46. (a) Waugh, J. S.; Fessenden, R. W. J. Am. Chem. Soc. 1957, 79, 846.
47. (b) Johnson, C. E.; Bovey, F. A. J. Chem. Phys. 1958, 29, 1012.
48. (c) Jonathan, N.; Gordon, S.; Dailey, B. P. J. Chem. Phys. 1962, 36, 2443.
49. (d) Barfield, M.; Grant, D. M.; Ikenberry, D. J. Am. Chem. Soc. 1975, 97, 6956.
50. (e) Agarwal, A.; Barnes, J. A.; Fletcher, J. L.; McGlinchey, M. J.; Saver, B. G. Can. J. Chem. 1977, 55, 2575.
51. (f) Haigh, C. W.; Mallion, R. B. Progress in NMR Spectroscopy; Pergamon Press, Ltd.: New York, 1980; Vol. 13, pp 303.
52. (a) Haigh, C. W.; Mallion, R. B. Mol. Phys. 1971, 22, 955.
53. (b) Haigh, C. W.; Mallion, R. B. Org. Magn. Reson. 1972, 4, 203.
54. (c) Dailey, B. P. J. Chem. Phys. 1964, 41, 2304.
55. 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, C.; 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. C.; 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. C.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, C.; 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.; and Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.:Wallingford, CT, 2004.
56. Hehre, J. W.; Radom, L.; von R. Schleyer, P. ; Pople, J. A. In Ab Initio Molecular Orbital Theory, Wiley & Sons,: New York, 1986.
57. Ditchfield, J. R. Mol. Phys. 1974, 27, 789.
58. Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497.
59. The lattice points ("ghost atoms") should be sensor points only without energy contribution in the present calculations. Only if HF calculations are applied is this proved to be true; in the case of electron correlation calculations, the "ghost atoms" get their own electron density and are of some influence on the energy of the studied molecule hereby. In these cases the TSNMRS surfaces proved to get heavily distorted. For the same reason, the 1H chemical shifts of the compounds studied were calculated on the same level of theory.
60. (a) Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, U.K., 2004. Zhou, O.; Fischer, J. E.; Coustel, N.; Kycia, S.; Zhu, Q.; McGhie, A. R.; Romanow, W. J.; McCauley, J. P., Jr.; Smith, A. B., III; Cox, D. E. Nature 1991, 351, 462.
61. (b) Soldatov, A. V.; Roth, C.; Dzyabchenko, A.; Johnels, D.; Lebedkin, S.; Meingast, C.; Sundquist, B.; Haluska, M.; Kuzmany, H. Science 2001, 293, 680.
62. SYBYL 7.3, Tripos Inc., St. Louis, MO 63144, 2007.