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From strong to weak NF bonds: on the design of a new class of fluorinating agents

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Abstract

A set of 50 molecules with NF bonds was investigated to determine the factors that influence the strength of a NF bond, with the aim of designing a new class of fluorinating agents. The intrinsic bond strength of the NF bonds was used as bond strength measure, derived from local stretching NF force constants obtained at the CCSD(T)/aug-cc-pVTZ and ωB97XD/aug-cc-pVTZ levels of theory. The investigation showed that the NF bond is a tunable covalent bond, with bond strength orders ranging from 2.5 (very strong) to 0.1 (very weak). NF bond strengthening is caused by a combination of different factors and can be achieved by e.g. ionization. Whereas, the NF bond weakening can be achieved by hypervalency on the N atom, using a N→Ch (Ch: O, S, Se) donor–acceptor type bond with different electron-withdrawing groups. These new insights into the nature of the NF bond were used to propose and design a new class of fluorinating agents. Hypervalent amine-chalcogenides turned out as most promising candidates for efficient electrophilic fluorinating agents.

Graphical abstract: From strong to weak NF bonds: on the design of a new class of fluorinating agents

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Publication details

The article was received on 17 Jun 2018, accepted on 30 Aug 2018 and first published on 31 Aug 2018


Article type: Paper
DOI: 10.1039/C8CP03843K
Citation: Phys. Chem. Chem. Phys., 2018, Advance Article
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    From strong to weak NF bonds: on the design of a new class of fluorinating agents

    D. Setiawan, D. Sethio, D. Cremer and E. Kraka, Phys. Chem. Chem. Phys., 2018, Advance Article , DOI: 10.1039/C8CP03843K

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