Polar substituent effects in the bicyclo[1.1.1]pentane ring system: Acidities of 3-substituted bicyclo[1.1.1]pentane-1-carboxylic acids

Journal of Organic Chemistry

Volumn 70, Issue 3, 2005, Pages 1029-1034

  Adcock, William ^a   Baran, Yakup ^b   Filippi, Antonello ^c   Speranza, Maurizio ^c   Trout, Neil A ^a  

^a FLINDERS UNIVERSITY   (Australia)

^b ZONGULDAK KARAELMAS UNIVERSITY   (Turkey)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; AROMATIC COMPOUNDS; CORRELATION METHODS; DATA ACQUISITION; PARAFFINS; PHASE COMPOSITION; SUBSTITUTION REACTIONS;

GAS-PHASE ACIDITIES; RING SYSTEM; SUBSTITUENT EFFECTS;

CARBOXYLIC ACIDS;

3 NITROBICYCLO[1.1.1]PENTANE 1 CARBOXYLIC ACID; 3 TRIMETHYLSILYLBICYCLO[1.1.1]PENTANE 1 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL REACTION; GAS; MATHEMATICAL COMPUTING; PKA; POTENTIOMETRIC TITRATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 13244275024     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040236b     Document Type: Article

References (46)

1. Applequist, D. E.; Renken, T. L.; Wheeler, J. W. J. Org. Chem. 1982, 47, 4985.
2. Adcock, W.; Blokhin, A. V.; Elsey, G. M.; Head, N. H.; Kristic, A. R.; Levin, M. D.; Michl, J.; Munton, J.; Pinkhassik, E.; Robert, M.; Saveant, J.-M.; Shtarev, A.; Stibor, I. J. Org. Chem. 1999, 64, 2618.
3. Wiberg, K. B. J. Org. Chem. 2002, 67, 1613.
4. Adcock, W.; Kristic, A. R. Magn. Reson. Chem. 2000, 38, 115.
5. Adcock, W.; Peralta, J. E.; Contreras, R. H. Magn. Reson. Chem. 2003, 41, 503.
6. Adcock, W.; Kristic, A. R. Magn. Reson. Chem. 1997, 35, 663.
7. (a) Roberts, J. D.; Moreland, W. T., Jr. J. Am. Chem. Soc. 1953, 75, 2167.
8. (b) Holtz, H. D.; Stock, L. M. J. Am. Chem. Soc. 1964, 86, 5188.
9. Koppel, I. A.; Mishima, M.; Stock, L. M.; Taft, R. W.; Topsom, R. D. J. Phys. Org, Chem. 1993, 6, 685.
10. Exner, O.; Böhm, S. Chem. Eur. J. 2002, 8, 5147 and references therein.
11. Adcock, W.; Anvia, R.; Butt, G.; Cook, A.; Duggan, P.; Grob, C. A.; Marriott, S.; Rowe, J.; Taegepera, M.; Taft, R. W.; Topsom, R. D. J. Phys. Org. Chem. 1991, 4, 353.
12. Adcock, W.; Trout, N. A. Chem. Rev. 1999, 99, 1415 and references therein.
13. (a) Adcock, W.; Kok, G. B.; Abeywickrema, A. N.; Kitching, W.; Drew, G. M.; Olszowy, H. A.; Schott, I. J. Am. Chem. Soc. 1983, 105, 290.
14. (b) Adcock, W.; Gangodawila, H.; Kok, G. B.; Iyer, V. S.; Kitching, W.; Drew, G. M.; Young, D. Organometallics 1987, 6, 156.
15. Adcock, W.; Butt, G.; Kok, G. B.; Marriott, S.; Topsom, R. D. J. Org. Chem. 1986, 50, 2551.
16. Adcock, W.; Abeywickrema, A. N.; Iyer, V. S.; Kok, G. B. Magn. Reson. Chem. 1986, 24, 213.
17. (a) Della, E. W.; Taylor, D. K. J. Org. Chem. 1994, 59, 2986.
18. (b) Taylor, D. K. Ph.D. Dissertation, Flinders University of South Australia, Adelaide, 1993.
19. (a) Della, E. W.; Tsanaktsidis, J. Aust. J. Chem. 1986, 39, 2061.
20. (b) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593.
21. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601.
22. Lochert, I. D. Ph.D. Dissertation, Flinders University of South Australia, Adelaide, 1996.
23. Adcock, W.; Binmore, G. T.; Krstic, A. R. Walton, J. C.; Wilkie, J. J. Am. Chem. Soc. 1995, 117, 2758.
24. (a) Meyers, I. A.; Pansegrau, P. D.; Ricker, W. F. J. Am. Chem. Soc. 1988, 110, 7178.
25. (b) Meyers, I. A. Gabel, R.; Mihelich, E. D. J. Org. Chem. 1978, 43, 1372.
26. th ed.; Longman: London, 1978.
27. (a) Murray, R. W.; Jeyaraman, R.; Mohan, L. Tetrahedron Lett. 1986, 27, 2335.
28. (b) Murray, R. W. Rajadhyaksha, S. N. Mohan, L. J. Org. Chem. 1989, 54, 5783.
29. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
30. (a) Cooks, R. G.; Kruger, T. L. J. Am. Chem. Soc. 1977, 99, 1279.
31. (b) McLuckey, S. A.; Cameron, D.; Cooks, R. G. J. Am. Chem. Soc. 1981, 103, 1313.
32. (c) Cooks, R. G.; Patrick, J. S.; Kotiaho, T.; McLuckey, S. A. Mass Spectrom. Rev. 1994, 13, 287.
33. (d) Cooks, R. G.; Koskinen, J. T.; Thomas, P. D. J. Mass Spectrom. 1999, 34, 85.
34. (e) Armentrout, P. B. J. Am. Soc. Mass Spectrom. 2000, 11, 371.
35. Fenn, J. B.; Mann, N.; Meng, C. K.; Wong, S. F. Mass Spectrom. Rev. 1990, 9, 37.
36. Gans, P.; Sabatini, A.; Vacca, A. J. Chem. Soc., Dalton Trans. 1985, 1195.
37. Shorter, J. Pure Appl. Chem. 1994, 66, 2451.
38. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D.3; Gaussian: Pittsburgh, PA, 1995.
39. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millan, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. 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, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A. 11.3; Gaussian: Pittsburgh, PA, 2002.
40. The isodesmic energies listed in Table 3 are uncorrected (0.98 ZVPE corrections effect only minor perturbations).
41. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165 and references therein.
42. (a) Westheimer, F. H.; Kirkwood, J. G. Trans. Faraday Soc. 1947, 43, 77 and references therein.
43. (b) Bowden, K.; Grubbs, E. J. Chem. Soc. Rev. 1996, 25, 171 and references therein.
44. (a) Charton, M. J. Phys. Org. Chem. 1999, 12, 275.
45. (b) Charton, M.; Charton, B. I. J. Chem. Soc., Perkin Trans. 2 1999, 2203.
46. Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Am. Chem. Soc. 1991, 56, 307.