The DOI matches its Crossref record; 9 of the 9 references it cites were found in a registry or an index.
Organic Fluorine: Odd Man Out
Abstract
Fluorine is special. Its presence in organic molecules is associated with unexpected properties, such as weak hydrogen-bond-acceptor strength (see figure) and striking differences between the behavior of aliphatic and aromatic hydrocarbon-fluorocarbon mixtures. Possible reasons are discussed.
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Cites
Ackermann, T. (1973) · Zeitschrift für Physikalische Chemie · doi:10.1524/zpch.1973.84.1-4.224 · Cited by 1,197
Organic Fluorine Hardly Ever Accepts Hydrogen Bonds
Dunitz, J. D., & Taylor, R. (1997) · Chemistry – A European Journal · doi:10.1002/chem.19970030115 · Cited by 943
Self-citationStructures of Molecules and Crystals of Fluoro-Carbons
BUNN, C. W., & HOWELLS, E. R. (1954) · Nature · doi:10.1038/174549a0 · Cited by 847
How good is fluorine as a hydrogen bond acceptor?
Howard, J. A. K., Hoy, V. J., O'Hagan, D., & Smith, G. T. (1996) · Tetrahedron · doi:10.1016/0040-4020(96)00749-1 · Cited by 737
C−H···F Interactions in the Crystal Structures of Some Fluorobenzenes
Thalladi, V. R., Weiss, H.-C., Bläser, D., Boese, R., Nangia, A., & Desiraju, G. R. (1998) · Journal of the American Chemical Society · doi:10.1021/ja981198e · Cited by 731
The chemistry of organic fluorine compounds
Seyferth, D. (1977) · Journal of Organometallic Chemistry · doi:10.1016/s0022-328x(00)89728-4 · Cited by 256
Shimoni, L., & Glusker, J. P. (1994) · Structural Chemistry · doi:10.1007/bf02252897 · Cited by 205
Collings, J. C., Roscoe, K. P., Robins, E. G., Batsanov, A. S., Stimson, L. M., Howard, J. A. K., Clark, S. J., & Marder, T. B. (2002) · New J. Chem. · doi:10.1039/b207102a · Cited by 196
Significant Inter- and Intramolecular O−H···FC Hydrogen Bonding
Barbarich, T. J., Rithner, C. D., Miller, S. M., Anderson, O. P., & Strauss, S. H. (1999) · Journal of the American Chemical Society · doi:10.1021/ja983552e · Cited by 125
Cited by
Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures
Salonen, L. M., Ellermann, M., & Diederich, F. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201007560 · Cited by 1,539
Successful fluorine-containing herbicide agrochemicals
Fujiwara, T., & O’Hagan, D. (2014) · Journal of Fluorine Chemistry · doi:10.1016/j.jfluchem.2014.06.014 · Cited by 894
A Practical Guide to the Design of Molecular Crystals
Corpinot, M. K., & Bučar, D.-K. (2019) · Crystal Growth & Design · doi:10.1021/acs.cgd.8b00972 · Cited by 348
Imino sugars are potent agonists of the human glucose sensor SGLT3
Voss, A. A., Díez-Sampedro, A., Hirayama, B. A., Loo, D. D. F., & Wright, E. M. (2007) · Molecular Pharmacology · doi:10.1124/mol.106.030288 · Cited by 59
Metadata
- Authors
- Dunitz, J. D.
- Venue
- ChemBioChem
- Publisher
- Wiley
- Published
- 2004-04-28
- Volume
- 5
- Issue
- 5
- Pages
- 614-621
- ISSN
- 1439-4227 (ISSN-L)
- 1439-7633
- OpenAlex
- W2146466816
- Cited by
- 423
- References
- 9
- FWCI
- 17.80
- Type
- journal article
- Language
- en
- Open access
- closed
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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).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
