Validity of the Hammett equation for isolated molecules: basicity of 3- and 4-substituted benzonitriles

Otto Exner; Stanislav Böhm

doi:10.1039/b404556d

journal article Jan 01, 2004

Validity of the Hammett equation for isolated molecules: basicity of 3- and 4-substituted benzonitriles

Otto Exner Stanislav Böhm

Physical Chemistry Chemical Physics Vol. 6 No. 14 pp. 3864-3871 · Royal Society of Chemistry (RSC)

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References

53

[1]

L. P. Hammett , Physical Organic Chemistry, McGraw-Hill, New York, 1970, ch. 11.9

[2]

O. Exner , Correlation Analysis of Chemical Data, Plenum Press, New York, 1988, ch. 2

[3]

Jaffé Chem. Rev. (1953) 10.1021/cr60165a003

[4]

van Bekkum Rec. Trav. Chim. Pays-Bas (1959) 10.1002/recl.19590781009

[5]

O. Exner , in Advances in Linear Free Energy Relationships, ed. N. Chapman and J. Shorter, Plenum, London, 1972, pp. 1–69

[6]

McMahon J. Am. Chem. Soc. (1977) 10.1021/ja00449a032

[7]

Taft Prog. Phys. Org. Chem. (1987) 10.1002/9780470171950.ch1

[8]

Jaffé J. Am. Chem. Soc. (1959) 10.1021/ja01521a026

[9]

Hine J. Am. Chem. Soc. (1959) 10.1021/ja01514a028

[10]

Ludwig Acta Chem. Scand. (1992) 10.3891/acta.chem.scand.46-0549

[11]

Reis J. Phys. Org. Chem. (1995) 10.1002/poc.610081006

[12]

Pross J. Org. Chem. (1980) 10.1021/jo01293a012

[13]

Exner Org. Reactivity (Tartu) (1995)

[14]

George J. Chem. Soc., Perkin Trans. 2 (1976) 10.1039/p29760001222

[15]

Exner Collect. Czech. Chem. Commun. (2001) 10.1135/cccc20011623

[16]

Böhm Int. J. Quantum Chem. (1984) 10.1002/qua.560260103

[17]

Exner Org. Reactivity (Tartu) (1979)

[18]

Sotomatsu J. Comput. Chem. (1989) 10.1002/jcc.540100109

[19]

Liu J. Chem. Inf. Comput. Sci. (2004) 10.1021/ci0342122

[20]

Wiberg J. Org. Chem. (2002) 10.1021/jo020100i

[21]

Exner J. Org. Chem. (2002) 10.1021/jo020172+

[22]

Wiberg J. Org. Chem. (2003) 10.1021/jo020560b

[23]

Liptak J. Am. Chem. Soc. (2002) 10.1021/ja012474j

[24]

Exner Prog. Phys. Org. Chem. (1990) 10.1002/9780470171974.ch4

[25]

Palát Jr. New J. Chem. (2002) 10.1039/b111156f

[26]

Charton Prog. Phys. Org. Chem. (1981) 10.1002/9780470171929.ch3

[27]

Castaño Struct. Chem. (1996) 10.1007/bf02275158

[28]

Maria Bull. Soc. Chim. Fr. (1995)

[29]

Bak J. Chem. Phys. (1962) 10.1063/1.1733422

[30]

Portalone J. Mol. Struct. (1987) 10.1016/0022-2860(87)87008-4

[31]

Hunter J. Phys. Chem. Ref. Data (1998) 10.1063/1.556018

[32]

Exner J. Chem. Soc., Perkin Trans. 2 (2002)

[33]

Density-functional exchange-energy approximation with correct asymptotic behavior

A. D. Becke

Physical Review A 1988 10.1103/physreva.38.3098

[34]

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density

Chengteh Lee, Weitao Yang, Robert G. Parr

Physical Review B 1988 10.1103/physrevb.37.785

[35]

Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr

Burkhard Miehlich, Andreas Savin, Hermann Stoll et al.

Chemical Physics Letters 1989 10.1016/0009-2614(89)87234-3

[36]

Density-functional thermochemistry. III. The role of exact exchange

Axel D. Becke

The Journal of Chemical Physics 1993 10.1063/1.464913

[37]

M. J. Frisch , G. W.Trucks, H. B.Schlegel, G. E.Scuseria, M. A.Robb, J. R.Cheeseman, J. A.Montgomery Jr., T.Vreven, K. N.Kudin, J. C.Burant, J. M.Millam, S. S.Iyengar, J.Tomasi, V.Barone, B.Mennucci, M.Cossi, G.Scalmani, N.Rega, G. A.Petersson, H.Nakatsuji, M.Hada, M.Ehara, K.Toyota, R.Fukuda, J.Hasegawa, M.Ishida, T.Nakajima, Y.Honda, O.Kitao, H.Nakai, M.Klene, X.Li, J. E.Knox, H. P.Hratchian, J. B.Cross, C.Adamo, J.Jaramillo, R.Gomperts, R. E.Stratmann, O.Yazyev, A. J.Austin, R.Cammi, C.Pomelli, J. W.Ochterski, P. Y.Ayala, K.Morokuma, G. A.Voth, P.Salvador, J. J.Dannenberg, V. G.Zakrzewski, S.Dapprich, A. D.Daniels, M. C.Strain, O.Farkas, D. K.Malick, A. D.Rabuck, K.Raghavachari, J. B.Foresman, J. V.Ortiz, Q.Cui, A. G.Baboul, S.Clifford, J.Cioslowski, B. B.Stefanov, G.Liu, A.Liashenko, P.Piskorz, I.Komaromi, R. L.Martin, D. J.Fox, T.Keith, M. A.Al-Laham, C. Y.Peng, A.Nanayakkara, M.Challacombe, P. M. W.Gill, B.Johnson, W.Chen, M. W.Wong, C.Gonzalez and J. A.Pople, Gaussian 03, Revision B.03, Gaussian Inc., Pittsburgh PA, 2003

[38]

Exner Chem. Eur. J. (2002) 10.1002/1521-3765(20021115)8:22<5147::aid-chem5147>3.0.co;2-t

[39]

Böhm New J. Chem. (2004) 10.1039/b305986c

[40]

Wiberg J. Org. Chem. (2003) 10.1021/jo030227n

[41]

Exner J. Am. Chem. Soc. (2001) 10.1021/ja003665+

[42]

Exner J. Phys. Org. Chem. (2004) 10.1002/poc.701

[43]

J. Shorter , Correlation Analysis of Organic Reactivity with Particular Reference to Multiple Regression, Research Studies Press,John Wiley & Sons, Chichester, 1982

[44]

Taft J. Phys. Chem. (1960) 10.1021/j100841a003

[45]

Ehrenson Prog. Phys. Org. Chem. (1973) 10.1002/9780470171899.ch1

[46]

Yukawa Bull. Chem. Soc. Jpn. (1959) 10.1246/bcsj.32.965

[47]

Yukawa Bull. Chem. Soc. Jpn. (1966) 10.1246/bcsj.39.2274

[48]

Pytela Collect. Czech. Chem. Commun. (1995) 10.1135/cccc19951502

[49]

Pytela Collect. Czech. Chem. Commun. (1996) 10.1135/cccc19960704

[50]

Exner Collect. Czech. Chem. Commun. (1966) 10.1135/cccc19660065

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Published: Jan 01, 2004
Vol/Issue: 6(14)
Pages: 3864-3871

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Cite This Article

Otto Exner, Stanislav Böhm (2004). Validity of the Hammett equation for isolated molecules: basicity of 3- and 4-substituted benzonitriles. Physical Chemistry Chemical Physics, 6(14), 3864-3871. https://doi.org/10.1039/b404556d

Validity of the Hammett equation for isolated molecules: basicity of 3- and 4-substituted benzonitriles

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