Limitations of Frontier Orbital and Charge Approaches in the Description of Electrophilic Aromatic Substitution

References (41)

1. 1 Knipe, A.C., and Moloney, M.G. (2020). Organic Reaction Mechanisms, Wiley. [DOI]
2. 2 Koerner, 1869, Fatti per servire alla determinazione del luogo chimico nelle sostanze aromatiche
3. 3 Koerner, 1874, Studi sull’isomeria delle così dette sostanze aromatiche a sei atomi di carbonio
4. 4 Kermack, 1922, An explanation of the property of induced polarity of atoms and an interpretation of the theory of partial valencies on an electronic basis [DOI]
5. 5 Lapworth, 1922, A theoretical derivation of the principle of induces alternate polarities [DOI]
6. 6 Saltzman, 1972, Arthur Lapworth [DOI]
7. 7 Karrer, P. (1965). Trattato di Chimica Organica, Sansoni.
8. 8 Wheland, 1942, A quantum mechanical investigation of the orientation of substitution in aromatic molecules [DOI]
9. 9 Olah, 1965, Stable carbonium ions. IX. Methylbenzenonium hexafluoroantimonates [DOI]
10. 10 Olah, 1967, Stable carbonium ions. LI. Fluorobenzenonium ions [DOI]
11. 11 Olah, 1972, Stable carbocations. CXXIV. Benzenium ion and monoalkylbenzenium ions [DOI]
12. 12 Corey, 1969, Directed conversion of the phenoxy grouping into a variety of cyclic polyfunctional systems [DOI]
13. 13 Hahn, 1974, Ipso nitration. II. Novel products and true positional selectivities in nitration of p-cymene [DOI]
14. 14 Carey, F.A., and Sundberg, R.J. (2008). Advanced Organic Chemistry, Springer. Part A: Structure and Mechanisms.
15. 15 Fukui, 1952, A molecular orbital theory of reactivity of aromatic hydrocarbons [DOI]
16. 16 Seeman, 2022, Kenichi Fukui, Frontier Molecular Orbital Theory, and the Woodward-Hoffmann Rules. Part II. A Sleeping Beauty in Chemistry [DOI]
17. 17 Elliott, 1982, Quantitative frontier orbital theory: Part I. Electrophilic aromatic substitution [DOI]
18. 18 Klopman, 1968, Chemical reactivity and the concept of charge- and frontier-controlled reactions [DOI]
19. 19 Salem, 1968, Intermolecular orbital theory of the interaction between conjugated systems. I. General theory [DOI]
20. 20 Salem, 1968, Intermolecular orbital theory of the interaction between conjugated systems. II. Thermal and photochemical cycloaddition [DOI]
21. 21 Domingo, L.R. (2016). Molecular Electron Density Theory: A Modern View of Reactivity in Organic Chemistry. Molecules, 21. [DOI]
22. 22 Stuyver, 2019, Electrophilic aromatic substitution reactions: Mechanistic landascape, electrostatic and electric-field control of reaction rates, and mechanistic crossovers [DOI]
23. 23 Galabov, 2016, Electrophilic aromatic substitution: New insighta into an old class of reactions [DOI]
24. 24 Liu, 2014, Where does the electron go? The nature of ortho/para and meta group directing in electrophilic aromatic substitution [DOI]
25. 25 (2025, July 28). Gaussian 09. Available online: https://barrett-group.mcgill.ca/tutorials/Gaussian%20tutorial.pdf.
26. 26 Parr, R.G., and Yang, W. (1989). Density Functional Theory of Atoms and Molecules, Oxford University Press.
27. 27 Becke, 1993, Density-functional thermochemistry. III. The role of exact exchange [DOI]
28. 28 Krukau, 2006, Influence of the exchange screening parameter on the performance of screened hybrid functionals [DOI]
29. 29 Adamo, 1999, Toward reliable density functional methods without adjustable parameters: The PBE0 model [DOI]
30. 30 Tao, 2003, Climbing the density functional ladder: Nonempirical meta-generalized gradient approximation designed for molecules and solids [DOI]
31. 31 Pounder, F.E. (1935). The Nitration of Nitrobenzene. [Ph.D. Thesis, Durham University].
32. 32 Baciocchi, 1972, Isomeric distributions and relative reactivities in the uncatalyzed chlorination of benzonitrile, nitrobenzene, and benzotrifluoride. The directive effects of electron-withdrawing substituents as a function of reagent and solvent [DOI]
33. 33 Ayers, 2018, Information-theoretic approaches to atoms-in.molecules: Hirshfeld family of partitioning schemes [DOI]
34. 34 Liu, 2015, Quantifying reactivity of electrophilic aromatic substitution reactions with Hirshfeld charge [DOI]
35. 35 Johnstone, J.F., Ridd, J.H., and Sandall, J.P.B. (1989). The borderline between the classical and the electron transfer process in nitration by the nitronium ion. Chem. Commun., 244–246. [DOI]
36. 36 Brown, 2013, Aromatic reactivity revealed: Beyond resonance theory and frontier orbitals [DOI]
37. 37 Davey, W., and Gwilt, J.R. (1950). The preparation of mononitrobenzaldehdes. J. Chem. Soc., 204–208. [DOI]
38. 38 Stock, L.M. (1968). Aromatic Substitution Reactions, Prentice-Hall.
39. 39 Kamm, 1923, Methyl m-nitrobenzoate [DOI]
40. 40 Yee, H.Y., and Boyle, A.J. (1955). The chlorination of benzoic acid in aqueous system by use of oxidizing acids. J. Chem. Soc., 4139–4140. [DOI]
41. 41 Pearson, 1963, The swamping catalyst effect. V. The halogenation of aromatic acid derivatives [DOI]

Cited by 7

Showing 1 of 7 known citations — external sources report more than can currently be individually listed.

Related research

• Participation of Phosphorylated Analogues of Nitroethene in Diels–Alder Reactions with Anthracene: A Molecular Electron Density Theory Study and Mechanistic Aspect — shares topic coverage
• On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions: A Critical Review — shares topic coverage
• On the Mechanism of the Synthesis of Nitrofunctionalised Δ2-Pyrazolines via [3+2] Cycloaddition Reactions between α-EWG-Activated Nitroethenes and Nitrylimine TAC Systems — shares topic coverage
• Diels–Alder Polar Reactions of Azaheterocycles: A Theoretical and Experimental Study — shares topic coverage
• Synthesis and Theoretical Studies of Aromatic Azaborines — shares topic coverage