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A free scan shows the junk files, broken settings and background clutter dragging Windows down - then fixes them in one click.Free scan · Windows 10 & 11A 2018 study ranked the kinetic reactivity of 10 commonly used electrophilic N–F fluorinating reagents using a shared set of 1,3-dicarbonyl model substrates. The measured rates spanned eight orders of magnitude, making the scale a useful starting point for reagent selection when the intended chemistry resembles the tested reactions—not a universal ranking for every substrate and condition.
What the scale measures
Electrophilic N–F fluorination forms a carbon–fluorine bond when a carbon nucleophile reacts with an N–F electrophile. In the study reported by Chemistry World, David Hodgson of Durham University and colleagues compared how quickly 10 commonly used reagents fluorinated 1,3-dicarbonyl model substrates. Their quantitative scale therefore describes reaction rates in that measured system, rather than an abstract measure of how much fluorinating power each reagent has.
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The reported rate range covers eight orders of magnitude. That large spread shows why reagent identity can matter substantially in this reaction class. The study is N. Rozatian et al., published in Chemical Science in 2018 (DOI: 10.1039/c8sc03596b). Chemistry World’s report summarizes the scale and its scope.
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How to use the ranking in reagent selection
Use the scale as a guide when the substrate and transformation are reasonably close to the study’s 1,3-dicarbonyl model reactions. A rate comparison in one reaction framework can help narrow candidates, but it cannot establish that the fastest reagent will give the best result for a different substrate or target position.
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- Reaction class: Favor kinetic data measured in chemistry similar to the intended electrophilic fluorination.
- Substrate scope and selectivity: Confirm whether the reagent works with the nucleophile and site you need; the model-substrate scale does not establish performance for all substrates.
- Solvent and conditions: Treat the ranking as conditional on its measured setup, and assess the effects of the conditions required for your own reaction.
- Stability and handling: Reagent power is not the only practical consideration. Stability and moisture sensitivity can affect how a reagent is stored and used.
- Mechanism: Make sure the desired process is electrophilic N–F transfer rather than radical fluorination, which calls for different evidence.
A 2021 review discusses these reagent classes, practical trade-offs, and distinct ways of comparing them. The review in the Beilstein Journal of Organic Chemistry names N-fluoropyridinium derivatives, N-fluorobenzenesulfonimide (NFSI), and Selectfluor among popular N–F agents studied in kinetic fluorination work. The available account does not give a complete tabulated ordering or all reagent-specific rate constants, so those details should not be inferred from the reported overall range.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Why kinetic reactivity is not the same as fluorinating power
A measured rate answers how quickly a particular reaction proceeds under specified conditions. Other quantitative measures answer different questions. The 2021 review distinguishes kinetic reactivity scales from calculated Fluorine Plus Detachment (FPD) energy and N–F homolytic bond-dissociation energy. Neither energy measure can be substituted directly for an experimentally measured electrophilic fluorination rate.
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N–F bond-dissociation data may be relevant when considering radical fluorination, but they do not, by themselves, rank electrophilic transfer rates. Keeping the mechanism and measurement type clear prevents a ranking for one purpose from being misapplied to another.
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The 2021 review reports that Selectfluor, NFSI, and N-fluoropyridinium salt derivatives are manufactured commercially on a large scale. It also describes stability and non-hygroscopic behavior as useful practical properties, while some highly powerful reagents can present moisture-sensitivity or handling trade-offs. These general observations do not establish local stock, current pricing, or availability from a particular supplier.
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