Ionic hydrogen bond effects on the acidities, basicities, solvation, solvent bridging, and self-assembly of carboxylic groups

Journal of the American Chemical Society

Volumn 121, Issue 33, 1999, Pages 7625-7635

  Meot Ner, Michael ^a,b   Elmore, Donald E ^c,d   Scheiner, Steve ^c  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^c SOUTHERN ILLINOIS UNIVERSITY   (United States)

^d CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID;

ACID BASE BALANCE; ARTICLE; HYDROGEN BOND; PH; PROTON TRANSPORT; SOLVATION;

EID: 0033603860     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982173i     Document Type: Article

References (43)

1. Kebarle, P. Annu. Rev. Phys. Chem. 1977, 28, 445; Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1257 and 1265.
2. Kebarle, P. Annu. Rev. Phys. Chem. 1977, 28, 445; Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1257 and 1265.
3. Castleman, A. W.; Keesee, R. G. Chem. Rev. 1986, 86, 589; Meot- Ner (Mautner), M.; Speller, C. V. J. Phys. Chem. 1986, 90, 6616; Hiraoka, K.; Takimoto, H.; Morise, K. J. J. Am. Chem. Soc. 1986, 108, 5683; Hiraoka, K. Bull. Chem. Soc. Jpn. 1987, 60, 2555.
4. Castleman, A. W.; Keesee, R. G. Chem. Rev. 1986, 86, 589; Meot-Ner (Mautner), M.; Speller, C. V. J. Phys. Chem. 1986, 90, 6616; Hiraoka, K.; Takimoto, H.; Morise, K. J. J. Am. Chem. Soc. 1986, 108, 5683; Hiraoka, K. Bull. Chem. Soc. Jpn. 1987, 60, 2555.
5. Castleman, A. W.; Keesee, R. G. Chem. Rev. 1986, 86, 589; Meot- Ner (Mautner), M.; Speller, C. V. J. Phys. Chem. 1986, 90, 6616; Hiraoka, K.; Takimoto, H.; Morise, K. J. J. Am. Chem. Soc. 1986, 108, 5683; Hiraoka, K. Bull. Chem. Soc. Jpn. 1987, 60, 2555.
6. Castleman, A. W.; Keesee, R. G. Chem. Rev. 1986, 86, 589; Meot- Ner (Mautner), M.; Speller, C. V. J. Phys. Chem. 1986, 90, 6616; Hiraoka, K.; Takimoto, H.; Morise, K. J. J. Am. Chem. Soc. 1986, 108, 5683; Hiraoka, K. Bull. Chem. Soc. Jpn. 1987, 60, 2555.
7. Meot-Ner (Mautner), M. J. Phys. Chem. 1987, 91, 417.
8. Meot-Ner (Mautner), M.; Sieck, L. W. J. Am. Chem. Soc. 1986, 108, 7525.
9. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1988, 110, 3854.
10. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1988, 110, 3075.
11. Deakyne, C. A.; Meot-Ner (Mautner), M.; Campbell, C. L.; Hughes, M. G.; Murphy, S. P. J. Chem. Phys. 1986, 90, 4648.
12. Grimsrud, E. P.; Kebarle, P. J. Am. Chem. Soc. 1973, 95, 7939.
13. Payzant, J. D.; Cunningham, A. J.; Kebarle, P. Can. J. Chem. 1973, 51, 3242.
14. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1986, 108, 6189.
15. Meot-Ner (Mautner), M.; Sieck, L. W. J. Am. Chem. Soc. 1991, 113, 4448.
16. Bartmess, J. E.; Scott, J. A.; McIver, R. T. J. Am. Chem. Soc. 1979, 101, 6046.
17. (a) Frurip, D. J.; Curtiss, L. A.; Blander, M. J. Am. Chem. Soc. 1980, 102, 2610.
18. (b) Curtiss, L. A.; Frurip, D. J.; Blander, M. J. Phys. Chem. 1982, 86, 1120.
19. (c) Mikhailova, O. K.; Solomentseva, T. V.; Markuzin, N. P. VINITI; Deposited Document 1999-81, 1981.
20. Frisch, M. J.; et al. In Gaussian, Inc.; Pittsburgh PA, 1993.
21. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
22. Rohlfing, C. M.; Allen, L. C.; Cook, C. M.; Schlegel, H. B. J. Chem. Phys. 1983, 78, 2498.
23. Desmeules, P. J.; Allen, L. C. J. Chem. Phys. 1980, 72, 4731.
24. Scheiner, S.; Harding, L. B. J. Am. Chem. Soc. 1981, 103, 2169.
25. Scheiner, S. Acc. Chem. Res. 1985, 18, 174.
26. Scheiner, S.; Szczesniak, M. M.; Bigham, L. D. Int. J. Quantum Chem. 1983, 23, 739.
27. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1982, 104, 6255.
28. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Ion Energetics Data. In NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD 20899, August 1997 (http://webbook.nist.gov).
29. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Ion Energetics Data. In NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD 20899, August 1997 (http://webbook.nist.gov).
30. Yamdagni, R.; Kebarle, P. J. Am. Chem. Soc. 1973, 95, 3504.
31. Larson, W. J.; McMahon, T. B. J. Am. Chem. Soc. 1984, 106, 517.
32. Meot-Ner (Mautner), M. In Molecular Structure and Energetics; Greenberg, A., Liebman, J. F., Eds.; VCH Publishers: Deerfield Beach, FL; 1987, Vol. 4, p 71.
33. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1265; J. Am. Chem. Soc. 1992, 114, 3312.
34. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1265; J. Am. Chem. Soc. 1992, 114, 3312.
35. Lifshitz, C.; Feng, W. Y. Int. J. Mass Spectrom. Ion Processes 1995, 146, 223.
36. Feng, W. Y.; Lifshitz, C. J. Mass Spectrom. 1995, 30, 1179.
37. Hargreaves, W. R.; Deamer, D. W. Biochemistry 1978, 17, 3759.
38. Basch, H.; Stevens, W. J. J. Am. Chem. Soc. 1991, 113, 95.
39. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1994, 116, 7848.
40. Sharma, R. B.; Kebarle, P. J. Am. Chem. Soc. 1984, 106, 6193.
41. Wei, S.; Tzeng, W. B.; Castleman, A. W. J. Phys. Chem. 1991, 95, 585. Wei, S.; Tzeng, W. B.; Castleman, A. W. Z. Phys. D, 1991, 20, 47.
42. Wei, S.; Tzeng, W. B.; Castleman, A. W. J. Phys. Chem. 1991, 95, 585. Wei, S.; Tzeng, W. B.; Castleman, A. W. Z. Phys. D, 1991, 20, 47.
43. Meot-Ner (Mautner), M.; Scheiner, S.; Yu, W. O. J. Am. Chem. Soc. 1998, 120, 6980.