Collect. Czech. Chem. Commun. 2004, 69, 984-995
https://doi.org/10.1135/cccc20040984

Attenuation of the Substituent Effects Along the Aliphatic Chain

Stanislav Böhma and Otto Exnerb,*

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

References

1a. Ingold C. K.: Structure and Mechanism in Organic Chemistry, Chap. II–7a,b. Cornell University Press, Ithaca 1953.
1b. Vereshchagin A. N.: Induktivnyi Effekt. Nauka, Moskva 1987.
1c. Exner O.: Correlation Analysis of Chemical Data, Chaps 2.3 and 3.5. Plenum Press, New York 1988.
2. Minkin V. I.: Pure Appl. Chem. 1999, 71, 1919. <https://doi.org/10.1351/pac199971101919>
3a. Carey F. A.: Organic Chemitry, 3rd ed., pp. 139 and 770. McGraw–Hill, New York 1996.
3b. Solomons T. W. G.: Organic Chemistry, 5th ed., p. 763. John Wiley & Sons, New York 1992.
4a. Smallwood H. M.: J. Am. Chem. Soc. 1932, 54, 3048. <https://doi.org/10.1021/ja01347a004>
4b. Schwarzenbach G., Egli H.: Helv. Chim. Acta 1934, 17, 1183. <https://doi.org/10.1002/hlca.193401701148>
5. Branch G. E. K., Calvin M.: The Theory of Organic Chemistry, pp. 201–216. Prentice-Hall, New York 1941.
6a. Exner O., Friedl Z.: Prog. Phys. Org. Chem. 1993, 19, 259. <https://doi.org/10.1002/9780470171981.ch4>
6b. Exner O.: J. Phys. Org. Chem. 1999, 12, 265. <https://doi.org/10.1002/(SICI)1099-1395(199904)12:4<265::AID-POC124>3.0.CO;2-O>
7a. Bowden K., Grubbs E. J.: Chem. Soc. Rev. 1996, 25, 171. <https://doi.org/10.1039/cs9962500171>
7b. Charton M.: J. Phys. Org. Chem. 1999, 12, 275. <https://doi.org/10.1002/(SICI)1099-1395(199904)12:4<275::AID-POC125>3.0.CO;2-K>
8. Wiberg K. B.: J. Org. Chem. 2002, 67, 1613. <https://doi.org/10.1021/jo011051x>
9a. 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>
9b. Exner O., Böhm S.: Chem. Eur. J. 2003, 9, 4718. <https://doi.org/10.1002/chem.200304807>
9c. Exner O., Böhm S.: J. Phys. Org. Chem. 2004, 17, 124. <https://doi.org/10.1002/poc.701>
10. Charton M., Charton B. I.: J. Chem. Soc., Perkin Trans. 2 1999, 2203. <https://doi.org/10.1039/a901495k>
11a. Exner O. in: Advances in Linear Free Energy Relationships (N. B. Chapman and J. Shorter, Eds), pp. 1–69. Plenum Press, London 1972.
11b. Litvinenko L. M., Popova R. C., Popov A. F.: Usp. Khim. 1975, 44, 1593. <https://doi.org/10.1070/RC1975v044n09ABEH002372>
12a. Palm V. A.: Osnovy kolichestvennoi teorii organicheskikh reaktsii, Chap. VII, § 2. Khimiya, Leningrad 1967.
12b. Vereshchagin A. N.: Induktivnyi Effekt, Chap. III.5.2. Nauka, Moskva 1987.
13. Yamdagni R., Kebarle P.: Can. J. Chem. 1974, 52, 861. <https://doi.org/10.1139/v74-137>
14. Hine J.: Structural Effects on Equilibria in Organic Chemistry, Chap. 3-6b. Wiley-Interscience, New York 1975.
15. Exner O., Fiedler P.: Collect. Czech. Chem. Commun. 1980, 45, 1251. <https://doi.org/10.1135/cccc19801251>
16. Iliceto A., Fava A., Simeone A.: Gazz. Chim. Ital. 1960, 90, 660.
17. George P., Trachtman M., Bock C. W., Brett A. M.: J. Chem. Soc., Perkin Trans. 2 1976, 1222. <https://doi.org/10.1039/p29760001222>
18. Exner O., Nauš P.: J. Phys. Org. Chem. 2000, 13, 693. <https://doi.org/10.1002/1099-1395(200011)13:11<693::AID-POC300>3.0.CO;2-2>
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>
20a. Došen-Mićović L., Jeremić D., Allinger N. L.: J. Am. Chem. Soc. 1983, 105, 1716. <https://doi.org/10.1021/ja00345a003>
20b. Došen-Mićović L., Jeremić D., Allinger N. L.: J. Am. Chem. Soc. 1983, 105, 1723. <https://doi.org/10.1021/ja00345a004>
21. 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 2003.
22. Böhm S., Exner O.: Org. Biomol. Chem. 2003, 1, 1176. <https://doi.org/10.1039/b212298g>
23. For instance, attempts were unsuccessful to determine the gas-phase acidity of 2-chloroethanol: Gal J.-F., Maria P.-C.: Personal communication.
24. Yoder C. S., Yoder C. H.: J. Am. Chem. Soc. 1980, 102, 1245. <https://doi.org/10.1021/ja00524a004>
25a. Friedl Z.: Can. J. Chem. 1985, 63, 1068. <https://doi.org/10.1139/v85-181>
25b. Friedl Z., Böhm S.: Collect. Czech. Chem. Commun. 1990, 55, 2880. <https://doi.org/10.1135/cccc19902880>
26. An almost identical opinion was offered by Hammett already in 1970: “Both the inductive effect and the electric field effect should be recognized as methods of mathematical approximation... The temptation to treat them as distinct physical phenomena should, however, be firmly resisted”. Hammett L. P.: Physical Organic Chemistry, 2nd ed., p. 376. McGraw–Hill, New York 1970.