2019
DOI: 10.1021/acs.accounts.9b00554
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Quest for a Symmetric [C–F–C]+ Fluoronium Ion in Solution: A Winding Path to Ultimate Success

Abstract: In this Account, we chronicle our tortuous but ultimately fruitful quest to synthesize a [C−F−C] + fluoronium ion in solution, thus providing the last piece of the organic halonium ion puzzle. Inspiration for the project can be traced all the way back to the graduate career of the corresponding author, wherein the analogy between a [C−H− C]+ "hydrido" bridge and a hypothetical [C−F−C] + bridge was first noted. The earliest attempt to construct a bicyclo[5.3.3]tridecane-based fluoronium ion (based on the analog… Show more

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Cited by 6 publications
(4 citation statements)
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“…The crystal structure of the fluoronium ion precursor was determined [ 50 ]; the structure of this ion taken from the Cambridge Structural Database, CSD [ 17 , 18 ] is presented in Figure 3 . The direct observation of the similar symmetrical [CFC] + ion was described recently [ 49 ], this is a stable species in solution and it was characterised by 19 F, 1 H, and 13 C NMR.…”
Section: The Case Of Halogen Bondssupporting
confidence: 59%
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“…The crystal structure of the fluoronium ion precursor was determined [ 50 ]; the structure of this ion taken from the Cambridge Structural Database, CSD [ 17 , 18 ] is presented in Figure 3 . The direct observation of the similar symmetrical [CFC] + ion was described recently [ 49 ], this is a stable species in solution and it was characterised by 19 F, 1 H, and 13 C NMR.…”
Section: The Case Of Halogen Bondssupporting
confidence: 59%
“…It was proved in numerous earlier and recent studies that the heavier halogen atom (Cl, Br, I) may be engaged in the hypervalent link in solution possessing formally positive charge. Such a link was usually doubted for the fluorine centre; the studies of Lectka and co-workers discussed here [ 49 , 50 ] are related to this challenge. However, it was evidenced only indirectly the occurrence of the fluoronium ion as a short-lived reaction intermediate [ 50 ].…”
Section: The Case Of Halogen Bondsmentioning
confidence: 86%
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“…The interaction of C–F bonds, especially in proteins, with proximate functional groups is a topic of lively interest and discussion. Their importance in dictating protein structure and function is not yet fully answered, including the dilemma of whether such interactions themselves are due to propinquity, attractive interactions, or a combination thereof. Over the past several years we have investigated close interactions between C–F bonds and common organic functional groups in relatively small molecules that are often dictated by forced proximity, along with some measure of attraction and repulsion. The case of the amide NH···F interaction is presumably one of the more interesting, due to the ubiquity of amide residues in proteins. Nevertheless, a search of the Cambridge Crystallographic Database (CCD) indicates only a few substantial interactions; most are self-evidently weak and long-range.…”
mentioning
confidence: 99%