The interplay of thio(seleno)amide/vinylogous thio(seleno) amide "resonance" and the anisotropic effect of thiocarbonyl and selenocarbonyl functional groups

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6592-6602

  Kleinpeter, Erich ^a   Schulenburg, Anja ^a   Zug, Ines ^b   Hartmann, Horst ^b  

^a UNIVERSITY OF POTSDAM   (Germany)

^b University of Applied Sciences Merseburg   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANISOTROPY; COALESCENCE; CONFORMATIONS; ISOMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ISOCHEMICAL SHIELDING SURFACES (ICSS); NATURAL BOND ORBITAL (NBO); ROTATION BARRIERS; THIOCARBONYL;

NITROGEN COMPOUNDS;

ACRYLAMIDE DERIVATIVE; FUNCTIONAL GROUP; ORGANOSELENIUM DERIVATIVE; PHENYL GROUP; SELENOCARBONYL GROUP; THIOAMIDE; THIOCARBONYL GROUP; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

AB INITIO CALCULATION; ANALYTIC METHOD; ANISOTROPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; GIAO METHOD; ISOCHEMICAL SHIELDING SURFACE; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; ROTATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 23644442095     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0503097     Document Type: Article

References (68)

1. (a) Steward, W. E.; Siddal, T. H. Chem. Rev. 1970, 70, 517.
2. (b) Jackman, L. M. Dynamic NMR Spectroscopy; Academic Press: San Francisco, 1975.
3. (c) Lambert, J. B., Takeuchi, Y., Eds. Acyclic Organonitrogen Stereodynamics; VCH: New York, 1992.
4. (a) Wiberg, K. B.; Bereneman, C. M. J. Am. Chem. Soc. 1992, 114, 831.
5. (b) Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644.
6. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1995, 117, 2201.
7. Wiberg, K. B.; Rush, D. J. J. Am. Chem. Soc. 2001, 123, 2038.
8. Laidig, E. K.; Cameron, L. M. J. Am. Chem. Soc. 1996, 118, 1737.
9. Quinonero, D.; Frontera, A.; Capo, M.; Ballester, P.; Suner, G. A.; Garau, C.; Deya, P. M. New J. Chem. 2001, 25, 259.
10. Fogarasi, G.; Szalay, P. G. J. Phys. Chem. A 1997, 101, 1400.
11. Ferretti, V.; Bertolasi, V.; Gilli, P.; Gilli, G. J. Phys. Chem. 1993, 97, 13568.
12. Hambley, T. W.; Hibbs, D. E.; Turner, P.; Howard, S. T.; Hursthouse, M. B. J. Chem. Soc., Perkin Trans. 2 2002, 235.
13. Prasad, B. V.; Uppal, P.; Bassi, P. S. Chem. Phys. Lett. 1997, 276, 31.
14. Kim, W.; Lee, H.-J.; Choi, J.-H.; Yoon, C.-J. J. Chem. Soc., Faraday Trans. 1998, 2663.
15. Ou, M.-C.; Chu, S.-Y. J. Phys. Chem. 1995, 99, 556.
16. Piccinni, C.; Fabre, O.; Zimmermann, D.; Reisse, J.; Cornea, F.; Fulea, C. Can. J. Chem. 1977, 55, 2649.
17. Glendening, E. D.; Hrabal, J. A., II. J. Am. Chem. Soc. 1997, 117, 12940.
18. Bharatam, P. V.; Moudgil, R.; Kaur, D. J. Phys. Chem. A 2003, 107, 1627.
19. Mo, Y.; von Rague Schleyer, P.; Wo, W.; Lin, M.; Zhang, Q.; Gao, J. J. Phys. Chem. A 2003, 107, 10011.
20. (a) Dabrowski, J.; Kozerski, L. J. Chem. Soc., Chem. Commun. 1968, 586.
21. (b) Dabrowski, J.; Kozerski, L. J. Chem. Phys. B 1971, 345.
22. Dabrowski, J.; Tencer, M. Bull. Chem. Soc. Jpn. 1975, 48, 1310 and references therein.
23. Siebert, H.-Ch.; Tajkhorsshid, E.; Dabrowski, J. J. Phys. Chem. A 2001, 105, 8488.
24. Dabrowski, J.; Kamienska-Trela, K. Org. Magn. Reson. 1972, 4, 421.
25. Kleinpeter, E.; Schroth, W.; Pihlaja, K. Magn. Reson. Chem. 1991, 29, 223.
26. (a) Kleinpeter, E.; Spitzner, R.; Schroth, W.; Pihlaja, K. J. Prakt. Chem. 1990, 332, 841.
27. (b) Kleinpeter, E.; Spitzner, R.; Schroth, W. Magn. Reson. Chem. 1987, 25, 688.
28. (c) Kleinpeter, E.; Pulst, M. J. Prakt. Chem. 1980, 322, 575.
29. (d) Kleinpeter, E.; Heinrich, B.; Pulst, M. Z. Chem. 1978, 18, 220.
30. (e) Kleinpeter, E.; Pulst, M. J. Prakt. Chem. 1977, 319, 1003.
31. (f) Kleinpeter, E.; Pulst, M. Z. Chem. 1977, 17, 339.
32. Pulst, M.; Greif, D.; Kleinpeter, E. Z. Chem. 1988, 28, 345 and references therein.
33. Kleinpeter, E.; Pulst, M. Org. Magn. Reson. 1977, 9, 308 and references therein.
34. Kleinpeter, E.; Tadesse, T.; Abegaz, B. J. Prakt. Chem. 1986, 328, 120.
35. Rablen, P. R.; Miller, D. A.; Bullock, V. R.; Hutchinson, P. H.; Gorman, J. A. J. Am. Chem. Soc. 1999, 121, 218.
36. Kleinpeter, E.; Klod, S.; Rudorf, W.-D. J. Org. Chem. 2004, 69, 4317.
37. Kaur, S.; Eberhardt, E. S.; Doucette, A.; Chase, A.; Dalby, C. J. Org. Chem. 2002, 67, 3937.
38. Forster, J. B.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
39. Pihlaja, K.; Kleinpeter, E. In Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis; VCH Publishers: New York, 1994.
40. Kleinpeter, E.; Pulst, M. Z. Chem. 1985, 25, 336.
41. Klod, S.; Kleinpeter, E. J. Chem. Soc., Perkin Trans. 2 2001, 1893.
42. Sandström, J. In Dynamic NMR Spectroscopy; Academic Press: London, 1982.
43. Behrendt, S.; Borsdorf, R.; Kleinpeter, E.; Gründel, D.; Hantschmann, A. Z. Chem. 1976, 16, 405.
44. Rae, I. D.; Wade, M. J. Int. J. Sulfur Chem. 1976, 8, 519.
45. Kleinpeter, E. J. Mol. Struct. 1996, 380, 139.
46. Kleinpeter, E.; Koch, A.; Taddei, F. J. Mol. Struct. 2001, 535, 257.
47. Benassi, R.; Bertarini, C.; Hilfert, L.; Kempter, G.; Kleinpeter, E.; Spindler, J.; Taddei, F.; Thomas, St. J. Mol. Struct. 2000, 520, 273.
48. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonnian, J.; Frisch, M. J. Phys. Chem. 1996, 100, 16098.
49. Forster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
50. Balasubrahmanyam, S. N.; Bharathi, S. N.; Usha, G. Org. Magn. Reson. 1983, 21, 474.
51. Szalontai, G.; Dudas, J. Acta Chim. Hung. 1985, 119, 7.
52. Kalinowski, O.; Lubosch, W.; Seebach, D. Chem. Ber. 1977, 110, 3733.
53. (a) Hartmann, H.; Heyde, C.; Zug, I. Synthesis 2000, 805.
54. (b) Noack, A.; Hartmann, H. Tetrahedron 2002, 58, 2137.
55. Zug, I.; Hartmann, H. Z. Naturforsch. 2002, 57b, 420.
56. Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1 and references therein.
57. Arnold, Z. Collect. Czech. Chem. Commun. 1961, 26, 3031.
58. Keil, D.; Hartmann, H. Phosphorus, Sulfur, Silicon 1999, 152, 169.
59. (a) Liebscher, J.; Hartmann, H. Z. Chem. 1974, 14, 358.
60. (b) Liebscher, J.; Hartmann, H. Z. Chem. 1975, 15, 16.
61. Hartmann, H.; Reuther, I. J. Prakt. Chem. 1973, 315, 144.
62. Keil, D.; Hartmann, H. Synthesis 2004, 15.
63. (a) Knoll, A.; Meissner, G.; Reist, K.; Liebscher, J. Z. Chem. 1983, 23, 19.
64. (b) Liebscher, J.; Mitzner, E. Synthesis 1985, 414.
65. Klayman, D. L.; Griffins, T. S. J. Am. Chem. Soc. 1973, 95, 197.
66. 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: Madison, WI, 2001.
67. 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.
68. SYBYL 6.9; Tripos, Inc.: St. Louis, MO, 2003.