Collect. Czech. Chem. Commun. 2004, 69, 2183-2192
https://doi.org/10.1135/cccc20042183

Substituent Effects on the Acidity of Weak Acids. 4. Anilinium Ions

Kenneth B. Wiberg

Department of Chemistry, Yale University, New Haven, CT 06520-8107, U.S.A.

References

1a. Wiberg K. B:. J. Org. Chem. 2002, 67, 1613. <https://doi.org/10.1021/jo011051x>
1b. Exner O., Böhm S.: J. Phys. Org. Chem. 2004, 17, 124. <https://doi.org/10.1002/poc.701>
1c. Exner O., Böhm S.: Chem. Eur. J. 2002, 8, 5147. <https://doi.org/10.1002/1521-3765(20021115)8:22<5147::AID-CHEM5147>3.0.CO;2-T>
2a. Wiberg K. B.: J. Org. Chem. 2002, 67, 4787. <https://doi.org/10.1021/jo020100i>
2b. Böhm S., Fiedler P., Exner O.: New J. Chem. 2004, 28, 67. <https://doi.org/10.1039/b305986c>
2c. Exner O., Böhm S.: J. Org. Chem. 2002, 67, 6320. <https://doi.org/10.1021/jo020172+>
3. Wiberg K. B.: J. Org. Chem. 2003, 68, 875. <https://doi.org/10.1021/jo020560b>
4a. Lau Y. K., Nishizawa K., Tse A., Brown R. S., Kebarle P.: J. Am. Chem. Soc. 1981, 103, 6291. <https://doi.org/10.1021/ja00411a004>
4b. Lau Y. K., Kebarle P.: J. Am. Chem. Soc. 1976, 98, 7452. <https://doi.org/10.1021/ja00439a072>
4c. Rolli E., Houriet R.: Spectrosc. Int. J. 1984, 3, 177.
4d. Maria P.-C., Leito I., Gal J.-F., Exner O., Decouzon M.: Bull. Soc. Chem. Fr. 1995, 132, 394.
5a. Russo N., Toscano M., Grand A., Mineva T.: J. Phys. Chem. A 2000, 104, 4017. <https://doi.org/10.1021/jp991949e>
5b. Bagno A., Terrier F.: J. Phys. Chem. A 2001, 105, 6537. <https://doi.org/10.1021/jp010439t>
5c. Bagno A., Scorrano G.: J. Phys. Chem. 1996, 100, 1536. <https://doi.org/10.1021/jp9518419>
5d. Pollack S. K., Devlin J. L., Summerhays K. D., Taft R. W., Hehre W. J.: J. Am. Chem. Soc. 1977, 99, 4583. <https://doi.org/10.1021/ja00456a008>
5e. Summerhays K. D., Pollack S. K., Hehre W. J.: J. Am. Chem. Soc. 1977, 99, 5585. <https://doi.org/10.1021/ja00456a009>
6. Hunter E. P. L., Lias G. G.: J. Phys. Chem. Ref. Data 1998, 27, 413. <https://doi.org/10.1063/1.556018>
7a. Purvis G. D., Bartlett R. J.: J. Chem. Phys. 1982, 76, 1910. <https://doi.org/10.1063/1.443164>
7b. Bartlett R. J., Purvis G. D.: Int. J. Quantum Chem. 1978, 14, 516. <https://doi.org/10.1002/qua.560140504>
8. Greenberg A., Venzanzi C. A.: J. Am. Chem. Soc. 1993, 115, 6951. <https://doi.org/10.1021/ja00068a064>
9. Exner O., Böhm S.: Phys. Chem. Chem. Phys. 2004, 6, 3864. <https://doi.org/10.1039/b404556d>
10. NIST Chemistry Webbook: www.webbook.nist.gov.
11. For another recent examination of the interaction between substituents, see Liu L., Fu Y., Liu R., Li R.-Q., Gio Q.-X.: J. Chem. Inf. Comput. Sci. 2004, 44, 652. <https://doi.org/10.1021/ci0342122>
12. Pearson B. D.: Proc. Chem. Soc. 1962, 78.
13. 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., Millam 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., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Baboul A. G., Cioslowski J., 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., Gonzalez C., Head-Gordon M., Replogle E. S., Pople J. A.: Gaussian 99, Development Version (Rev. B.04). Gaussian, Inc., Pittsburgh (PA) 1998.