The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Circuit Resonance Energy: A Key Quantity That Links Energetic and Magnetic Criteria of Aromaticity
Abstract
Energetic and magnetic criteria of aromaticity are different in nature and sometimes make different predictions as to the aromaticity of a polycyclic pi-system. Thus, some charged polycyclic pi-systems are aromatic but paratropic. We derived the individual circuit contributions to aromaticity from the magnetic response of a polycyclic pi-system and named them circuit resonance energies (CREs). Each CRE has the same sign and essentially the same magnitude as the corresponding cyclic conjugation energy (CCE) defined by Bosanac and Gutman. Such CREs were found to play a crucial role in associating the energetic criteria for determining the degree of aromaticity with the magnetic ones. We can now interpret both energetic and magnetic criteria of aromaticity consistently in terms of CREs. Ring-current diamagnetism proved to be the tendency of a cyclic pi-system to retain aromatic stabilization energy (ASE) at the level of individual circuits.
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Cites
Nucleus-Independent Chemical Shifts: A Simple and Efficient Aromaticity Probe
Schleyer, P. V. R., Maerker, C., Dransfeld, A., Jiao, H., & van Eikema Hommes, N. J. R. (1996) · Journal of the American Chemical Society · doi:10.1021/ja960582d · Cited by 6,210
To 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
Steiner, E., & Fowler, P. W. (2001) · The Journal of Physical Chemistry A · doi:10.1021/jp011955m · Cited by 459
Cited by
Calculations of magnetically induced current densities: theory and applications
Sundholm, D., Fliegl, H., & Berger, R. J. F. (2016) · WIREs Computational Molecular Science · doi:10.1002/wcms.1270 · Cited by 373
Szczepanik, D. W., Solà, M., Andrzejak, M., Pawełek, B., Dominikowska, J., Kukułka, M., Dyduch, K., Krygowski, T. M., & Szatylowicz, H. (2017) · Journal of Computational Chemistry · doi:10.1002/jcc.24805 · Cited by 107
Metadata
- Authors
- Aihara, J.-I.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-02-08
- Volume
- 128
- Issue
- 9
- Pages
- 2873-2879
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2010222643
- Cited by
- 159
- References
- 3
- FWCI
- 7.98
- Type
- journal article
- Language
- en
- Open access
- closed
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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