An NMR investigation of the existence of halide and carboxylate co-solute effects on the rotational barrier about the C-N bonds in urea and thiourea

Journal of Physical Organic Chemistry

Volumn 23, Issue 9, 2010, Pages 806-809

  Gerken, James B ^a   Ross, Scott ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Halide; Hydrogen bond; Rotational barrier; Thiourea; Urea

Indexed keywords

ACETONITRILE SOLUTIONS; H-BONDS; HALIDE; HYDROGEN BONDINGS; LINE-SHAPE ANALYSIS; PROTON NMR; ROTATIONAL BARRIERS; SOLUTE EFFECTS; VARIABLE-TEMPERATURE NMR;

ACETONITRILE; ACIDITY; CARBOXYLATION; HYDROGEN; HYDROGEN BONDS; METABOLISM; NEGATIVE IONS; THIOUREAS;

UREA;

EID: 77957060620     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1665     Document Type: Article

References (26)

1. For a recent review, see A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743.
2. M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 10558-10559.
3. I. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404-13405.
4. S. E. Reisman, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 7198-7199.
5. An example where the anion is cyanide, see S. C. Pan, B. List, Org. Lett. 2007, 9, 1149-1151.
6. K. A. Haushalter, J. Lau, J. D. Roberts, J. Am. Chem. Soc. 1996, 118, 8891-8896.
7. P. Stilbs, S. Forsén, J. Phys. Chem. 1971, 75, 1901-1902.
8. Y. Zhao, M. K. Raymond, H. Tsai, J. D. Roberts, J. Phys. Chem. 1993, 97, 2910-2913.
9. A reviewer helpfully reminded us of this approach, which if employed would be complicated due to additional temperature dependencies of the viscosity and correlation time. For an example of successful exploitation of this effect in the low-viscosity limit, see S. Gaemers, C. J. Elsevier, Chem. Soc. Rev. 1999, 28, 135-141.
10. J. A. Happe, J. Phys. Chem. 1961, 65, 72-76.
11. P. S. Belton, I. J. Cox, R. K. Harris, J. Chem. Soc. Faraday Trans. 2 1985, 81, 63-75.
12. M. H. Abraham, Chem. Soc. Rev. 1993, 22, 73-83.
13. M. H. Abraham, R. J. Abraham, J. Byrne, L. Griffiths, J. Org. Chem. 2006, 71, 3389-3394.
14. S. J. Zuend, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 15872-15883.
15. S. Rashdan, M. E. Light, J. D. Kilburn, Chem. Commun. 2006, 4578-4580.
16. C. Amman, P. Meier, A. E. Merbach, J. Magn. Reson. 1982, 46, 319-321.
17. H. Sun, S. G. DiMagno, J. Am. Chem. Soc. 2005, 127, 2050-2051.
18. J. D. Roberts, J. Am. Chem. Soc. 1956, 78, 4495-4496.
19. H. M. Ratajczak, J. A. Ladd, J. Mol. Liquids 1984, 29, 97-103.
20. H. Eyring, Rev. Mod. Phys. 1962, 34, 616-619.
21. M. H. Abraham, Y. H. Zhao, J. Org. Chem. 2004, 69, 4677-4685.
22. D. E. Gómez, L. Fabbrizzi, M. Licchelli, E. Monzani, Org. Biomol. Chem. 2005, 3, 1495-1500.
23. C. M. Pearce, J. K. M. Sanders, J. Chem. Soc. Perkin I 1994, 1119-1124.
24. D. A. Jose, A. Singh, A. Das, B. Ganguly, Tet. Lett. 2007, 48, 3695-3698.
25. G. A. Kumar, Y. Pan, C. J. Smallwood, M. A. McAllister, J. Comp. Chem. 1998, 19, 1345-1352.
26. T. Schwabe, S. Grimme, Acc. Chem. Res. 2008, 41, 569-579.