The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
Relation between the Substituent Effect and Aromaticity
Abstract
Molecular geometries of benzene and its 18 monosubstituted derivatives were optimized at B3LYP/6-311+G** level of theory. The changes of pi-electron delocalization of the benzene fragment were estimated by use of aromatic stabilization energies (ASE) based on different homodesmotic reaction schemes, geometry-based HOMA model, magnetism-based NICS, NICS(1), NICS(1)zz, and an electronic delocalization index, PDI, derived from the AIM theory. Apart from aromatic stabilization energies the other descriptors of aromaticity vary to a very small extent, indicating high resistance of the pi-electron structure to the substituent effect. This is somewhat analogous to a tendency of benzene systems to retain their initial pi-electron structure during the reaction course that leads to aromatic substitution.
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Cites
Krygowski, T. M. (1993) · Journal of Chemical Information and Computer Sciences · doi:10.1021/ci00011a011 · Cited by 1,320
Self-citationTo What Extent Can Aromaticity Be Defined Uniquely?
Cyrañski, M. K., Krygowski, T. M., Katritzky, A. R., & Schleyer, P. V. R. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo016255s · Cited by 727
Self-citation
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Fallah-Bagher-Shaidaei, H., Wannere, C. S., Corminboeuf, C., Puchta, R., & Schleyer, P. V. R. (2006) · Organic Letters · doi:10.1021/ol0529546 · Cited by 1,257
Poater, J., Duran, M., Solà, M., & Silvi, B. (2005) · Chemical Reviews · doi:10.1021/cr030085x · Cited by 803
Self-citationMagnetic criteria of aromaticity
Gershoni-Poranne, R., & Stanger, A. (2015) · Chem. Soc. Rev. · doi:10.1039/c5cs00114e · Cited by 494
Advanced oxidation processes for the removal of mono and polycyclic aromatic hydrocarbons—A review
Rayaroth, M. P., Marchel, M., & Boczkaj, G. (2023) · Science of The Total Environment · doi:10.1016/j.scitotenv.2022.159043 · Cited by 158
Computational Study of Bond Dissociation Enthalpies for Substituted β‐O‐4 Lignin Model Compounds
Younker, J. M., Beste, A., & Buchanan, A. C. (2011) · ChemPhysChem · doi:10.1002/cphc.201100477 · Cited by 106
Metadata
- Authors
- Krygowski, T. M., Ejsmont, K., Stepień, B. T., Cyrański, M. K., Poater, J., & Solà, M.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-09-10
- Volume
- 69
- Issue
- 20
- Pages
- 6634-6640
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2063068258
- Cited by
- 193
- References
- 2
- FWCI
- 5.08
- Type
- journal article
- Language
- en
- Open access
- closed
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