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In-Plane Aromaticity in 1,3-Dipolar Cycloadditions. Solvent Effects, Selectivity, and Nucleus-Independent Chemical Shifts
Abstract
The aromaticity and the regiochemistry of several 1,3-dipolar cycloadditions have been studied computationally. It is found that all the transition structures associated with concerted supra-supra processes are in-plane aromatic, and this aromaticity is compatible with a ring current circulating along the molecular plane. Solvent effects enhance the activation barrier of the reaction and diminish its synchronicity, with little impact on aromaticity. According to our calculations, aromaticity is important but does not determine the regiochemistry of the reaction. Other phenomena such as electrostatic interactions and solvent effects can modify the regiochemical and the stereochemical outcome.
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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
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Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion
Chen, Z., Wannere, C. S., Corminboeuf, C., Puchta, R., & Schleyer, P. V. R. (2005) · Chemical Reviews · doi:10.1021/cr030088+ · Cited by 3,847
Self-citationWhich NICS Aromaticity Index for Planar π Rings Is Best?
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
Self-citationFernández, I., & Bickelhaupt, F. M. (2014) · Chem. Soc. Rev. · doi:10.1039/c4cs00055b · Cited by 803
Cyrański, M. K. (2005) · Chemical Reviews · doi:10.1021/cr0300845 · Cited by 638
Theoretical Methods for the Description of the Solvent Effect in Biomolecular Systems
Orozco, M., & Luque, F. J. (2000) · Chemical Reviews · doi:10.1021/cr990052a · Cited by 622
Metadata
- Authors
- Cossío, F. P., Morao, I., Jiao, H., & Schleyer, P. V. R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-07-01
- Volume
- 121
- Issue
- 28
- Pages
- 6737-6746
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2087037012
- Cited by
- 233
- References
- 1
- FWCI
- 9.83
- Type
- journal article
- Language
- en
- Open access
- closed
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- Cossío, F. P., Morao, I., Jiao, H., & Schleyer, P. V. R. (1999). In-Plane Aromaticity in 1,3-Dipolar Cycloadditions. Solvent Effects, Selectivity, and Nucleus-Independent Chemical Shifts. Journal of the American Chemical Society. https://doi.org/10.1021/ja9831397
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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