Effects of solvents on the tautomerization of N,N-dimethylglycine

Journal of Physical Organic Chemistry

Volumn 10, Issue 12, 1997, Pages 898-900

  Headley, Allan D ^a   Corona, Rita E ^a   Cheung, Eric T ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

N,N dimethylglycine tautomerization; Solvation; Solvent effect; Zwitterion

Indexed keywords

EID: 0009744288     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-1395(199712)10:12<898::aid-poc959>3.0.co;2-k     Document Type: Article

References (32)

1. J. Shorter, Correlation Analysis of Organic Reactivity. Research Studies Press, New York (1982).
2. A. Rini, P. D. Maria, A. Guarnieri and J. Varoli, J. Pharm. Sci. 76, 48 (1987).
3. (a) A. D. Headley, M. E. McMurry and S. D. Starnes, J. Org. Chem. 59, 1863 (1994)
4. (b) A. D. Headley and S. D. Starnes, J. Am. Chem. Soc. 117, 9309 (1995)
5. (c) A. D. Headley and S. D. Starnes, J. Mol. Struct. (THEOCHEM) 370, 147 (1996).
6. A. D. Headley, E. T. Cheung and B. Patel, Tetrahedron Lett. 37, 6673 (1996).
7. S. Gupta, Chem. Rev. 87, 1183 (1987).
8. (a) P. A. Haberfield, J. Chem. Educ. 57, 346 (1980)
9. (b) J. P. Greenstein and M. Wintz, Chemistry of Amino Acids. Wiley, New York (1961).
10. G. M. Barrow, J. Am. Chem. Soc. 80, 86 (1958).
11. (a) G. Alagona, C. Ohio and P. A. Kollman, J. Mol. Struct. (THEOCHEM) 166, 385 (1988)
12. (b) G. Alagona and C. Ghio, J. Mol. Liq. 47, 139 (1990)
13. (c) J. W.-O. Tam and C. P. Nash, J. Phys. Chem. 76, 4033 (1972)
14. (d) D. A. Horsma and C. P. Nash, J. Phys. Chem. 72, 2351 (1968).
15. D. I. Hughes, J. J. Bergan and E. J. Grabowski, J. Org. Chem. 51, 2579 (1986).
16. D. E. Leahy, P. W. Carr, R. S. Pearlman, R. W. Taft and M. J. Kamlet, Chromatographia 21, 473 (1986).
17. (a) J. Parra-Mouchet and R. E. Contreras, Int. J. Quantum Chem. 31, 41 (1988)
18. (b) S. K. Chakravorty and S. C. Lahiri, J. Indian Chem. Soc. 64, 399 (1987).
19. G. Gorman, J. P. Speir, C. A. Turner and I. J. Amster, J. Am. Chem. Soc. 114, 3986 (1992).
20. M. J. Kamlet, R. M. Doherty, M. H. Abraham and R. W. Taft, Quant. Struct.-Act. Relat. 7, 71 (1988).
21. (a) J. B. Cummings and P. Karbarle, Can. J. Chem. 56, 1 (1978)
22. (b) M. J. Locke and R. T. McIver, J. Am. Chem. Soc. 105, 4226 (1983)
23. (c) G. C. Caldwell, R. Renneboog and P. Karbarle, Can. J. Chem. Soc. 67, 611 (1989)
24. (d) J. F. Bartmess, J. A. Scott and R. T. MeIver, J. Am. Chem. Soc. 101, 6046 (1979)
25. (e) J. I. Brauman and L. K. Blair, J. Am. Chem. Soc. 90, 5636 (1968)
26. (f) R. T. Melver and J. H. Silvers, J. Am. Chem. Soc. 95, 8462 (1973)
27. (g) S. T. Graul, M. E. Schnute and R. R. Squire, Int. J. Mass Spectrom. Ion Processes 96, 181 (1990).
28. (a) G. Alagona and C. Ghio, J. Mol. Liq. 47, 139 (1990)
29. (b) G. Alagona, C. Chio and P. A. Kollman, J. Mol. Struct. (THEOCHEM) 166, 385 (1988).
30. (a) C. Jinfeng and R. D. Topsom, J. Mol. Struct. (THEOCHEM) 188, 45 (1989)
31. (b) R. D. Topsom, Prog. Phys. Org. Chem. 17, 107 (1990).
32. A. D. Headley, J. Org. Chem. 56, 3688 (1991).