Collect. Czech. Chem. Commun. 2006, 71, 1239-1255
https://doi.org/10.1135/cccc20061239

Analysis of the Ortho Effect: Basicity of 2-Substituted Benzonitriles

Otto Exnera,* and Stanislav Böhmb

a Institute of Organic Chemistry and Biochemistry, 166 10 Prague 6, Czech Republic
b Department of Organic Chemistry, Institute of Chemical Technology, Prague, 166 28 Prague 6, Czech Republic

References

1. Charton M.: Prog. Phys. Org. Chem. 1971, 8, 235. <https://doi.org/10.1002/9780470171875.ch3>
2. Böhm S., Fiedler P., Exner O.: New J. Chem. 2004, 28, 67. <https://doi.org/10.1039/b305986c>
3a. Brown H. C., McDaniel D. H., Häfliger O. in: Determination of Organic Structures by Physical Methods (E. A. Braude and F. C. Nachod, Eds), p. 567. Academic Press, New York 1955.
3b. Hammond G. S. in: Steric Effects in Organic Chemistry (M. S. Newman, Ed.), p. 425. Wiley, New York 1956.
3c. Hine J.: Structural Effects on Equilibria in Organic Chemistry, Chaps 3, 4. Wiley, New York 1975.
4. Shorter J. in: Advances in Linear Free Energy Relationships (N. B. Chapman and J. Shorter, Eds), p. 71. Plenum Press, London 1972.
5a. Fujita T., Nishioka T.: Prog. Phys. Org. Chem. 1976, 12, 49. <https://doi.org/10.1002/9780470171912.ch3>
5b. Berg U., Gallo R., Klatte G., Metzger J.: J. Chem. Soc., Perkin Trans. 2 1980, 1350. <https://doi.org/10.1039/p29800001350>
5c. Farthing A. C., Nam B. in: Steric Effects in Conjugated Systems (G. W. Gray, Ed.), p. 131. Butterworths, London 1958.
6. Charton M. in: Similarity Models in Organic Chemistry, Biochemistry and Related Fields (R. I. Zalewski, T. M. Krygowski and J. Shorter, Eds), p. 629. Elsevier, Amsterdam 1991.
7. Bowden K., Manser G. E.: Can. J. Chem. 1968, 46, 2941. <https://doi.org/10.1139/v68-488>
8. Charton M.: Can. J. Chem. 1960, 38, 2493. <https://doi.org/10.1139/v60-338>
9a. Nummert V., Piirsalu M., Lepp M., Mäemets V., Koppel I.: Collect. Czech. Chem. Commun. 2005, 70, 198. <https://doi.org/10.1135/cccc20050198>
9b. Nummert V., Piirsalu M., Mäemets V., Koppel I.: Collect. Czech. Chem. Commun. 2006, 71, 107. <https://doi.org/10.1135/cccc20060107>
9c. Bauerová I., Ludwig M.: Collect. Czech. Chem. Commun. 2001, 66, 770. <https://doi.org/10.1135/cccc20010770>
10a. Pytela O., Liška J.: Collect. Czech. Chem. Commun. 1994, 59, 2005. <https://doi.org/10.1135/cccc19942005>
10b. Pytela O, Prusek O.: Collect. Czech. Chem. Commun. 1999, 64, 1617. <https://doi.org/10.1135/cccc19991617>
11. Fiedler P., Böhm S., Kulhánek J., Exner O.: Org. Biomol. Chem. 2006, 4, 2003. <https://doi.org/10.1039/b601875k>
12a. Pross A., Radom L., Taft R. W.: J. Org. Chem. 1980, 45, 818. <https://doi.org/10.1021/jo01293a012>
12b. Exner O.: Org. Reactiv. 1995, 29, 1.
13. George P., Trachtman M., Bock C. W., Brett A. M.: J. Chem. Soc., Perkin Trans. 2 1976, 1222. <https://doi.org/10.1039/p29760001222>
14. McMahon T. B., Kebarle P.: J. Am. Chem. Soc. 1977, 99, 2222. <https://doi.org/10.1021/ja00449a032>
15. Böhm S., Gal J.-F., Maria P.-C., Kulhánek J., Exner O.: Eur. J. Org. Chem. 2005, 2580. <https://doi.org/10.1002/ejoc.200400837>
16a. Exner O., Böhm S.: J. Org. Chem. 2002, 67, 6320. <https://doi.org/10.1021/jo020172+>
16b. Exner O., Böhm S.: J. Phys. Org. Chem. 2004, 17, 124. <https://doi.org/10.1002/poc.701>
16c. Böhm S., Exner O.: Collect. Czech. Chem. Commun. 2005, 70, 370. <https://doi.org/10.1135/cccc20050370>
17. Exner O., Böhm S., Decouzon M., Gal J.-F., Maria P.-C.: J. Chem. Soc., Perkin Trans. 2 2002, 168.
18. Exner O., Böhm S.: Phys. Chem. Chem. Phys. 2004, 6, 3864. <https://doi.org/10.1039/b404556d>
19a. Becke A. D.: Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098. <https://doi.org/10.1103/PhysRevA.38.3098>
19b. Lee C., Yang W., Parr R. G.: Phys. Rev. B.: Condens. Matter 1988, 37, 785. <https://doi.org/10.1103/PhysRevB.37.785>
19c. Miehlich B., Savin A., Stoll H., Preuss H.: Chem. Phys. Lett. 1989, 157, 200. <https://doi.org/10.1016/0009-2614(89)87234-3>
19d. Becke A. D.: J. Chem. Phys. 1993, 98, 5648. <https://doi.org/10.1063/1.464913>
20. Castaño O., Notario R., Hori K., Abboud J.-L. M.: Struct. Chem. 1996, 7, 321. <https://doi.org/10.1007/BF02275158>
21. Hunter E. P. L., Lias S. G.: J. Phys. Chem. Ref. Data 1998, 27, 413. <https://doi.org/10.1063/1.556018>
22. Thompson H. W., Steel G.: Trans. Faraday Soc. 1956, 52, 1451. <https://doi.org/10.1039/tf9565201451>
23. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A., Jr., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., 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., Gonzalez C., Pople J. A.: Gaussian 03, Revision B.03. Gaussian, Inc., Pittsburgh (PA) 2003.
24. Exner O., Böhm S.: Collect. Czech. Chem. Commun. 2001, 66, 1623. <https://doi.org/10.1135/cccc20011623>
25. Binev Y. I., Georgieva M. K., Daskalova L. I.: Spectrochim. Acta, Part A 2004, 60, 2601. <https://doi.org/10.1016/j.saa.2003.12.040>
26. Seguin J.-P., Guillaume-Vilpert F., Moutiers G., Guével E. L., Villien L., Terrier F.: J. Chem. Soc., Perkin Trans. 2 1997, 7.
27. Wiberg K. B.: J. Org. Chem. 2003, 68, 875. <https://doi.org/10.1021/jo020560b>
28. Austerheim Å., Gramstad T.: Acta Chem. Scand., Sect. B 1985, 39, 583. <https://doi.org/10.3891/acta.chem.scand.39b-0583>
29. Honda M., Fujii A., Fujimaki E., Ebata T., Mikami N.: J. Phys. Chem., A 2003, 107, 3678. <https://doi.org/10.1021/jp022504k>
30. Yonemoto T., Reynolds W. F.: Can. J. Chem. 1965, 43, 2668. <https://doi.org/10.1139/v65-373>
31. Pytela O., Otyepka M., Kulhánek J., Otyepková E., Nevěčná T.: J. Phys. Chem., A 2003, 107, 11489. <https://doi.org/10.1021/jp022664w>
32. Grabowski S. J.: J. Phys. Org. Chem. 2004, 17, 18. <https://doi.org/10.1002/poc.685>
33. Verloop A., Hoogenstraaten W., Tipker J. in: Drug Design (E. J. Ariens, Ed.), Vol. VII, p. 165. Academic Press, New York 1976.
34. Jaffé H. H.: Chem. Rev. 1953, 53, 191. <https://doi.org/10.1021/cr60165a003>