Electronic state of push-pull alkenes: An experimental dynamic NMR and theoretical ab initio MO study

Journal of Organic Chemistry

Volumn 69, Issue 13, 2004, Pages 4317-4329

  Kleinpeter, Erich ^a   Klod, Sabrina ^a   Rudorf, Wolf Dieter ^b  

^a UNIVERSITY OF POTSDAM   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; ELECTRON TRANSITIONS; ELECTRONIC DENSITY OF STATES; FREE ENERGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PERTURBATION TECHNIQUES;

CHEMICAL SHIFTS; ELECTRONIC STATE;

OLEFINS;

ALKENE DERIVATIVE; CARBON; CARBONYL DERIVATIVE; CYANIDE; HYDROGEN; OXYGEN; SOLVENT; SULFUR;

AB INITIO CALCULATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COVALENT BOND; ENERGY; GEOMETRY; HYDROGEN BOND; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; ROTATION; STEREOSPECIFICITY; THEORY;

EID: 3042783436     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0496345     Document Type: Article

References (68)

1. Sandström, J. Top. Stereochem. 1983, 14, 83.
2. Forni, A.; Destro, R. Chem. Eur. J. 2003, 9, 5528.
3. Fischer, G.; Rudorf, W.-D.; Kleinpeter, E. Magn. Reson. Chem. 1991, 29, 212.
4. Fischer, G.; Kleinpeter, E. Magn. Reson. Chem. 1991, 29, 204.
5. Kleinpeter, E.; Thomas, St.; Uhlig, G.; Rudorf, W.-D. Magn. Reson. Chem. 1993, 31, 714.
6. Kleinpeter, E.; Heydenreich, M.; Chatterjee, S. K.; Rudorf, W.-D. Magn. Reson. Chem. 1994, 32, 473.
7. Kleinpeter, E.; Koch, A.; Heydenreich, M.; Chatterjee, S. K.; Rudorf, W.-D. J. Mol. Struct. 1995, 356, 25.
8. Kleinpeter, E.; Heydenreich, M.; Woller, J.; Wolf, G.; Koch, A.; Kempter, G. J. Chem. Soc., Perkin Trans. 2 1998, 1877.
9. Dwyer, T. J.; Jasein, P. G. THEOCHEM 1996, 363, 139.
10. Benassi, R.; Bertarini, C.; Kleinpeter, E.; Taddei, F. THEOCHEM 2000, 498, 217.
11. (a) Marchand, P.; Frageau-Bellassoued, M.-C.; Bellec, C.; Lhommet, G. Synthesis 1994, 1118.
12. (b) Mueller, J. L.; Gibson, M. S.; Hartman, J. S. Can. J. Chem. 1996, 74, 1329.
13. (c) Morales-Rios, M. S.; Suarez-Castillo, O. R.; Alvarez-Cisneros, C.; Joseph-Nathan, P. Can. J. Chem. 1999, 77, 130.
14. (d) Morales-Rios, M. S.; Garcia-Velgara, M.; Cervantes-Cuevas, H.; Alvarez-Cisneros, C.; Joseph-Nathan, P. Magn. Reson. Chem. 2000, 38, 172.
15. (e) Lei, Y. Z.; Cerioni, G.; Rappoport, Z. J. Org. Chem. 2001, 66, 8379.
16. Abbotto, A.; Bradamante, S.; Capri, N.; Rzepa, H.; Williams, D. J.; White, A. J. Org. Chem. 1996, 61, 1770.
17. (a) Yavari, I.; Adib, M.; Bijanzadeh, H. R.; Sadegi, M. M. M.; Logmani-Khouzani, H.; Safari, J. Mh. Chem. 2002, 133, 1109.
18. (b) Rodriguez, R.; Suarez, M.; Ochoa, E.; Pita, B.; Espinosa, R.; Martin, N.; Quinteiro, M.; Seoane, E.; Soto, J.-L. J. Heterocycl. Chem. 1997, 34, 957.
19. (c) Suarez, M.; Ochoa, E.; Pita, B.; Espinosa, R.; L. Gonzales, L.; Martin, N.; Quinteiro, M.; Seoane, E.; Soto, J.-L. J. Heterocycl. Chem. 1997, 34, 931.
20. (d) Morales, A.; Suarez, M.; Ochoa, E.; Verdecia, Y.; Gonzalez, L.; Martin, N.; Quinteiro, M.; Seoane, E.; Soto, J.-L. J. Heterocycl. Chem. 1996, 33, 103.
21. (a) Michalik, M.; Evers, R. Wiss. Z. Univ. Rostock 1989, 38, 9.
22. (b) Evers, R.; Michalik, M. Wiss. Z. Univ. Rostock 1990, 39, 44.
23. (c) Michalik, M.; Freier, Th.; Reinke, H.; Peseke, K. J. Chem. Soc., Perkin Trans. 2 2002, 114.
24. Chiara, J. L.; Gomez-Sanchez, A.; Bellanato, J. J. Chem. Soc., Perkin Trans. 2 1992, 787.
25. Sin, H.-S.; Holler, M.; Gurger, A.; Biellmann, J.-F. Tetrahedron Lett. 1997, 38, 3585.
26. (a) Neuenschwander, M.; Bartlome, A. Helv. Chim. Acta 1991, 74, 1489.
27. (b) Bartlome, A.; Stämpfli, U.; Neuenschwander, M. Chimia 1991, 45, 346.
28. Morihashi, K.; Azuki, M.; Kikuchi, O. THEOCHEM 2001, 543, 233.
29. Zerner, M. C.; Reidlinger, C.; Fabian, W. M. F.; Junek, H. THEOCHEM 2001, 543, 129.
30. (a) Benassi, R.; Bertarini, C.; Hilfert, L.; Kempter, G.; Kleinpeter, E.; Spindler, J.; Taddei, F.; Thomas, St. J. Mol. Struct. 2000, 520, 273.
31. (b) Benassi, R.; Bertarini, C.; Kleinpeter, E.; Taddei, F.; Thomas, St. THEOCHEM 2000, 498, 201.
32. Benassi, R.; Bertarini, C.; Taddei, F.; Kleinpeter, E. THEOCHEM 2001, 541, 101.
33. Taddei, F. THEOCHEM 2001, 544, 141.
34. Møller, C.; Plesset, R. A. J. Phys. Rev. 1934, 46, 618.
35. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople J. A. In Ab Initio Molecular Orbital Theory, Wiley: New York, 1986.
36. Pihlaja, K.; Kleinpeter, E. In Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis; VCH Publishers, Inc.: New York, 1994.
37. (a) Klod, S.; Kleinpeter, E. J. Chem. Soc., Perkin Trans. 2 2001, 1893.
38. (b) Benassi, R.; Bertarini, C.; Hilfert, L.; Kempter, G.; Kleinpeter, E.; Spindler, J.; Taddei, F.; Thomas, St. J. Mol. Struct. 2000, 520, 273.
39. (a) Toth. G.; Kovacs, J.; Levai, A.; Koch, A.; Kleinpeter, E. Magn. Reson. Chem. 2001, 39, 251.
40. (b) Kovacs, J.; Toth, G.; Simon, A.; Levai, A.; Koch, A.; Kleinpeter, E. Magn. Reson. Chem. 2003, 41, 193.
41. Klod, S.; Koch, A.; Kleinpeter, E. J. Chem. Soc., Perkin Trans. 2 2002, 1506.
42. Ditchfield, J. R. Mol. Phys. 1974, 27, 789.
43. Cheeseman, J. P.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys, 1996, 104, 5497.
44. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonnian, J.; Frisch, M. J. J. Phys. Chem, 1996, 100, 16098.
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M.; Farkas, C. O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P.; Cui, Y. Q.; Morokuma, K. D.; Malick, K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L.; Gomperts, R.; Martin, L. R.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
46. (a) Douglas, J. E.; Rabinovitch, B. S.; Looney, F. S. J. Chem. Phys. 1955, 23, 315.
47. (b) Rabinovitch, B. S.; Michel, K.-W. J. Am. Chem. Soc. 1959, 81, 5056.
48. (c) Kristiakovsky, G. B.; Smith, W. R. J. Am. Chem. Soc. 1934, 56, 638.
49. Sandström, J. In Dynamic NMR Spectroscopy; Academic Press: London, 1982.
50. Shanan-Atidi, H.; Bar-Eli, K. H. J. Phys. Chem. 1970, 74, 961.
51. Kleinpeter, E.; Pulst, M. Org. Magn. Reson. 1977, 9, 308.
52. Kleinpeter, E. J. Mol. Struct. 1996, 380, 139.
53. Kleinpeter, E.; Koch, A. J. Phys. Org. Chem. 2001, 14, 566.
54. Adhikesavalu, D.; Kamath, N. U.; Venkatesan, K. Proc. Indian Acad. Sci. (Chem. Sci.) 1983, 92, 449.
55. (a) Alkorta, I.; Wentrup, C.; Elguero, J. THEOCHEM 2002, 585, 27.
56. (b) Bernhardt, P. V.; Koch, R.; Moloney, D. W. J.; Shtaiwi, M.; Wentrup, C. J. Chem, Soc., Perkin Trans. 2 2002, 515.
57. (c) Marcovic, R.; Shirazi, A.; Dzambaski, Z.; Baranac, M.; Minic, D. J. Serb. Chem. Soc. 2003, 68, 1.
58. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
59. Rudorf, W.-D.; Augustin, M.; Phosphorus Sulfur Relat. Elem. 1981, 9, 329.
60. Rudorf, W.-D. Ger. (East) DD 220028 A1 19850320, 1985; Chem. Abstr. 1986, 104, 68858.
61. Rudorf, W.-D. Tetrahedron 1980, 36, 1791. Rudorf, W.-D.; Augustin, M. J. J. Prakt. Chem. 1977, 319, 454.
62. Rudorf, W.-D. Tetrahedron 1980, 36, 1791. Rudorf, W.-D.; Augustin, M. J. J. Prakt. Chem. 1977, 319, 454.
63. Rudorf, W.-D.; Haase, C. Ger. (East), DD 240544 A1 19861105, 1986; Chem. Abstr. 1987, 107, 154324.
64. Willker, W.; Leibfritz, D.; Kerssebaum, R.; Bermel, W. Magn. Reson. Chem. 1993, 31, 287-292
65. Binsch, G. Top. Stereochem. 1968, 3, 97-192
66. Binsch, G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1980, 19, 411-429
67. Glending, E. D.; Baadenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales C. M.; Weinhold, F. NBO 5.0; Theoretical Chemistry Institute, University of Wisconson, WI, 2001.
68. SYBYL 6.9; Tripos Inc.: St. Louis, MO, 2003.