Gas-phase NMR studies of N,N-dimethylthioamides. Influence of the thiocarbonyl substituent on the internal rotation activation energies

Journal of Physical Chemistry A

Volumn 101, Issue 26, 1997, Pages 4699-4706

  Neugebauer Crawford, S M ^a   Taha, A N ^a   True, N S ^a   LeMaster, C B ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BOISE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; FREE ENERGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SULFUR COMPOUNDS;

AMIDES; THIOAMIDES;

NITROGEN COMPOUNDS;

EID: 0041836665     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp970953s     Document Type: Article

References (50)

1. Lehninger, A. L.; Nelson, D. L.; Cox, M. M. Principles of Biochemistry; Worth: New York, 1993.
2. Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644.
3. Stewart, W. E.; Sidall, T. H., III. Chem. Rev. 1970, 70 (5), 517.
4. Oki, M. Applications of Dynamic NMR Spectroscope to Organic Chmeistry; VCH: Deerfield Beach, FL, 1985.
5. Berg, U.; Blum, Z. J. Chem. Res. 1983, 206.
6. Drakenberg, T. J. Phys. Chem. 1976, 80 1023.
7. Feigel, M. J. Phys. Chem. 1983, 87, 3054.
8. Neuman, R. C., Jr.; Rourk, D. N.; Jonas, V. J. Am. Chem. Soc. 1967, 89, 3412.
9. Hobson, R. F.; Reeves, L. W.; Shaw, K. N. J. Phys. Chem. 1973, 77, 1228.
10. Sandstrom, J. J. Phys. Chem. 1967, 71, 2318.
11. Piccinni-Leopardi, C.; Omer, F.; Zimmerman, D.; Reisse, J. Can. J. Chem. 1977, 55, 2649.
12. Berg, U.; Grimaud, M.; Sandstom, J. Nouv. J. Chim. 1979, 3, 175.
13. Sidall, T. H., III; Stewart, W. E.; Knight, F. D. J. Phys. Chem. 1970, 74, 3580
14. Walter, W.; Schaumann, E.; Rose, H. Org. Magn. Reson. 1973, 5 (4), 191.
15. Isaksson, G.; Sandstrom, J. Acta Chem. Scand. 1967, 21(6) 1605.
16. Abboud, J. L. M.; Mo', O.; de-Paz, J. L. G.; Yanez, M.; Esseffar, M.; Bouab, W.; El-Mouhtadi, M.; Mokhlisse, R.; Ballesteros, E.; Herreros, M.; Homan, H.; Lopez-Mardomingo, C.; Notario, R. J. Am. Chem. Soc. 1993, 115, 12468.
17. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1995, 117, 2201.
18. Laidig, K. E.; Cameron, L. M. J. Am. Chem. Soc. 1996, 118, 1737
19. Feigel, M.; Strassner, T. J. Mol. Struct. 1993, 283, 33.
20. Walter, W.; Imbert, J. P. J. Mol. Struct. 1975, 29, 253.
21. Lim, K.-T.; Francl, M. M. J. Phys. Chem. 1987, 91, 2716.
22. Suarez, C.; LeMaster, C. B.; LeMaster, C. L.; Tafazzoli, M.; True, N. S. J. Phys. Chem. 1990, 94, 6679.
23. Goshorn, R. H.; Lewis, W. W., Jr.; Jaul, E.; Ritter, E. J. Org. Synth. 1955, 35, 551.
24. Wagner, R. B.; Zook, H. D. Synthetic Organic Chemistry; Wiley: New York, 1953.
25. (a) Stephenson, D. S.; Binsch, G. Program No. 365.
26. (b) LeMaster, C. B.; LeMaster, C. L.; True, N. S. Programs No. 569 and QCMP059. Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN 47405.
27. Ross, B. D.; True, N. S.; Decker, D. L. J. Phys. Chem. 1983, 87, 89.
28. 13C NMR spectra. See: Ross, B. D.; True, N. S. J. Am. Chem. Soc. 1984, 106, 2451.
29. Ou, M.-C.; Chu, S.-Y. J. Phys. Chem. 1995, 99, 556.
30. Jackman, J. L. In Dynamic Nuclear Magnetic Resonance Spectroscopy; Jackman, L. M., Cotton, F. A., Eds.; Academic Press: New York, 1975; pp 203-252, and references therein.
31. LeMaster, C. B.; True, N. S. J. Phys. Chem. 1989, 93, 1307.
32. True, N. S.; Suarez, C. Advances in Molecular Structure Research; JAI: London, 1995; Vol I. p 115.
33. Suarez, C.; LeMaster, C. B.; LeMaster C. L.; Tafazzoli, M.; True, N. S. J. Phys. Chem. 1990, 94, 6679.
34. Ross, B. D.; True, N. S.; Matson, G. B. J. Phys. Chem. 1984, 88, 2675.
35. Wiberg, K. B.; Rablen, P. R.; Rush, D. J.; Keith, T. A. J. Am. Chem Soc. 1995, 117, 4261.
36. Ross, B. D.; Wong, L. T.; True, N. S. J. Phys. Chem. 1985, 89, 836.
37. Allan, E. A.; Hobson, R. F.; Reeves, L. W.; Shaw, K. N. J. Am. Chem. Soc. 1972, 94, 6604.
38. Reeves, L. W.; Shaw, K. N. Can. J. Chem. 1971, 49, 3672.
39. 3 3.8 Å, as estimated from AMPAC results using the AM 1 Hamiltonian. Program No. 506, Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN 47405.
40. Beilstein, 4th ed., Springer-Verlag: Berlin, 1958; Vol. 1, Suppl. 3, p 161.
41. Pines, A.; Rabinovitz, M. Tetrahedron Lett. 1968, 3529.
42. Fryer, C. W.; Conti, F.; Franconi, C. Ric. Sci., Parte 2: Sez. A, 1965, 8, 788.
43. Neuman, R. C., Jr.; Young, L. B. J. Phys. Chem. 1965, 69, 2570.
44. Sunners, B.; Piette, L. H.; Schneider, W. G. Can. J. Chem. 1960, 38, 681.
45. Rogers, M. T.; Woodbrey, J. C. J. Phys. Chem. 1962, 66, 540.
46. Reeves, L. W.; Shaddick, R. C.; Shaw, K. N. Can. J. Chem. 1971, 49, 3683.
47. Neuman, R. C., Jr.; Jonas, V. J. Am. Chem. Soc. 1968, 90, 1970.
48. Ross, B. D.; True, N. S. J. Am. Chem. Soc. 1984, 106, 2451.
49. Drakenberg, T.; Dahlquist, K.; Forsen, S. J. J. Phys. Chem. 1972, 76 (15), 2178.
50. Woodbrey, J. C.; Rogers, M. T. J. Am. Chem. Soc. 1962, 84, 13.