Review article

https://doi.org/10.5562/cca3283

Nucleofugality of Leaving Groups

Mirela Matić ; University of Zareb, Faculty of Pharmacy and Biochemistry, Ante Kovačića 1, HR-10000 Zagreb, Croatia
Bernard Denegri ; University of Zareb, Faculty of Pharmacy and Biochemistry, Ante Kovačića 1, HR-10000 Zagreb, Croatia
Sandra Jurić ; University of Zareb, Faculty of Pharmacy and Biochemistry, Ante Kovačića 1, HR-10000 Zagreb, Croatia
Olga Kronja ; University of Zareb, Faculty of Pharmacy and Biochemistry, Ante Kovačića 1, HR-10000 Zagreb, Croatia

Abstract

In this short authors' review, a method for determining experimental and calculated nucleofugalities of leaving groups in a given solvents according to LFER equation log k = sf (Nf + Ef) is presented. Also, a comprehensive overview of the experimental and calculated nucleofuges specific parameters (Nf and sf) for various negatively charged and neutral leaving groups is shown. Some applications of the above method have been demonstrated: use of the electrofugalitiy and nucleofugality scales to estimate the reactivities of a variety of substrates in various solvents, as well as assessment whether a given substrate is stable in a given solvent for a sufficent amount of time, which may indicate if the substrate can be handled in the solvent of choice during synthetic and other procedures. The method can also be used to establish whether the relative reactivity of leaving groups depends on the electrofuge moiety of the substrate.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

nucleofugality; electrofugality; leaving group; solvolysis

Hrčak ID:

198666

URI

https://hrcak.srce.hr/198666

Publication date:

29.12.2017.

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