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Attractive Intramolecular Edge-to-Face Aromatic Interactions in Flexible Organic Molecules
Abstract
Recent X-ray crystallographic and NMR evidence indicates that relatively weak intramolecular edge-to-face interactions between aromatic rings can affect or determine the conformation of organic molecules in the solid state and in solution. Experimental estimates indicate that these interactions are energetically attractive by ca. 1.5 kcal mol(-1) but disfavored in solution by entropic factors due to the restricted internal mobility. Hence, these interactions are more manifest at low temperature in solution or in crystal structures where conformational entropy effects are negligible.
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Cited by
Self-assembled π-stacks of functional dyes in solution: structural and thermodynamic features
Chen, Z., Lohr, A., Saha-Möller, C. R., & Würthner, F. (2009) · Chem. Soc. Rev. · doi:10.1039/b809359h · Cited by 1,051
Carbon in One Dimension: Structural Analysis of the Higher Conjugated Polyynes
Szafert, S., & Gladysz, J. A. (2003) · Chemical Reviews · doi:10.1021/cr030041o · Cited by 398
Xie, Z., Yang, B., Li, F., Cheng, G., Liu, L., Yang, G., Xu, H., Ye, L., Hanif, M., Liu, S., et al. (2005) · Journal of the American Chemical Society · doi:10.1021/ja054661d · Cited by 382
Update 1 of: Carbon in One Dimension: Structural Analysis of the Higher Conjugated Polyynes
Szafert, S., & Gladysz, J. A. (2006) · Chemical Reviews · doi:10.1021/cr068016g · Cited by 269
Metadata
- Authors
- Jennings, W. B., Farrell, B. M., & Malone, J. F.
- Venue
- Accounts of Chemical Research
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-10-10
- Volume
- 34
- Issue
- 11
- Pages
- 885-894
- ISSN
- 0001-4842 (ISSN-L)
- 1520-4898
- OpenAlex
- W2057547754
- Cited by
- 409
- References
- 0
- FWCI
- 17.53
- 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).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
