The DOI matches its Crossref record; 5 of the 5 references it cites were found in a registry or an index.
Local Aromaticity of [n]Acenes, [n]Phenacenes, and [n]Helicenes (n= 1−9)
Abstract
The local aromaticity of the six-membered rings in three series of benzenoid compounds, namely, the [n]acenes, [n]phenacenes, and [n]helicenes for n = 1-9, has been assessed by means of three probes of local aromaticity based on structural, magnetic, and electron delocalization properties. For [n]acenes our analysis shows that the more reactive inner rings are more aromatic than the outer rings. For [n]phenacenes, all indicators of aromaticity show that the external rings are the most aromatic. From the external to the central ring, the local aromaticity varies in a damped alternate way. The trends for the [n]helicene series are the same as those found for [n]phenacenes. Despite the departure from planarity in [n]helicenes, only a very slight loss of aromaticity is detected in [n]helicenes as compared to the corresponding [n]phenacenes. Finally, because of magnetic couplings between superimposed six-membered rings in the higher members of the [n]helicenes series, we have demonstrated that the NICS indicator of aromaticity artificially increases the local aromaticity of their most external rings.
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Citations
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
Krygowski, T. M. (1993) · Journal of Chemical Information and Computer Sciences · doi:10.1021/ci00011a011 · Cited by 1,320
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
Poater, J., Fradera, X., Duran, M., & Solà, M. (2003) · Chemistry – A European Journal · doi:10.1002/chem.200390041 · Cited by 449
Self-citation
Cited by
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
Forty years of Clar's aromatic π-sextet rule
Solà, M. (2013) · Frontiers in Chemistry · doi:10.3389/fchem.2013.00022 · Cited by 473
Self-citationThe NICS‐ XY ‐Scan: Identification of Local and Global Ring Currents in Multi‐Ring Systems
Gershoni‐Poranne, R., & Stanger, A. (2014) · Chemistry – A European Journal · doi:10.1002/chem.201304307 · Cited by 348
A uniform approach to the description of multicenter bonding
Szczepanik, D. W., Andrzejak, M., Dyduch, K., Żak, E., Makowski, M., Mazur, G., & Mrozek, J. (2014) · Physical Chemistry Chemical Physics · doi:10.1039/c4cp02932a · Cited by 207
Metadata
- Authors
- Portella, G., Poater, J., Bofill, J. M., Alemany, P., & Solà, M.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-02-24
- Volume
- 70
- Issue
- 7
- Pages
- 2509-2521
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2005856936
- Cited by
- 224
- References
- 5
- FWCI
- 8.14
- Type
- journal article
- Language
- en
- Open access
- closed
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