The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
Scales of Nucleophilicity and Electrophilicity: A System for Ordering Polar Organic and Organometallic Reactions
Abstract
Contrary to widely held opinion, for many reactions in organic and organometallic chemistry it is possible to define nucleophilicity and electrophilicity parameters that are independent of the reaction partners. This phenomenon, discovered by Ritchie during the early 1970s for reactions of highly stabilized carbenium and diazonium ions with n‐nucleophiles, also occurs with reactions of carbenium ions with aliphatic and aromatic π‐electron systems and in hydride transfer reactions. With the aid of the scales of nucleophilicity and electrophilicity set out here, which extend over eighteen orders of magnitude, forecasts can be made about the feasibility and rate of a given CC bond formation, ionic reduction, or diazo coupling. Linkage with the reactivity scales of Ritchie and Sweigart/Kane‐Maguire enables a unified treatment of a large number of polar reactions.
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Cites
Nucleophilic reactivity constants toward methyl iodide and trans-dichlorodi(pyridine)platinum(II)
Pearson, R. G., Sobel, H. R., & Songstad, J. (1968) · Journal of the American Chemical Society · doi:10.1021/ja01004a021 · Cited by 455
Pienta, N. J., & Kessler, R. J. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00033a017 · Cited by 28
Cited by
Domingo, L. R., Aurell, M. J., Pérez, P., & Contreras, R. (2002) · Tetrahedron · doi:10.1016/s0040-4020(02)00410-6 · Cited by 1,075
Alabugin, I. V., Gilmore, K. M., & Peterson, P. W. (2011) · WIREs Computational Molecular Science · doi:10.1002/wcms.6 · Cited by 268
Quantifying Reductive Amination in Nonenzymatic Amino Acid Synthesis
Mayer, R. J., & Moran, J. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202212237 · Cited by 33
Modeling chemical reactions for drug design
Gasteiger, J. (2007) · Journal of Computer-Aided Molecular Design · doi:10.1007/s10822-006-9097-4 · Cited by 19
Metadata
- Authors
- Mayr, H., & Patz, M.
- Venue
- Angewandte Chemie International Edition in English
- Publisher
- Wiley
- Published
- 1994-05-18
- Volume
- 33
- Issue
- 9
- Pages
- 938-957
- ISSN
- 0570-0833 (ISSN-L)
- OpenAlex
- W2011529244
- Cited by
- 739
- References
- 2
- FWCI
- 12.32
- Type
- journal article
- Language
- en
- Open access
- closed
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- Mayr, H., & Patz, M. (1994). Scales of Nucleophilicity and Electrophilicity: A System for Ordering Polar Organic and Organometallic Reactions. Angewandte Chemie International Edition in English. https://doi.org/10.1002/anie.199409381
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