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• W2050871592 endingPage "5729" @default.
• W2050871592 startingPage "5722" @default.
• W2050871592 abstract "The reactions of 1,3-bis(bromomethyl)-2-fluorobenzene with the bis(trifluoroacetamides) of 1,3-bis(aminomethyl)-2-fluorobenzene and 1,3-bis(aminomethyl)benzene yield the respective 1+1-condensed [3.3]-m-cyclophanes, respectively termed F2-phane (yield 39%) and HF-phane (yield 48%) without trifluoroacetamide groups. The reactions of F2-phane with 1,8-diiodo-3,6-dioxaoctane and 1,11-diiodo-3,6,9-trioxaundecane result in the respective 1+1-addition products 1,10-diaza-25,26-difluoro-4,7-dioxatetracyclo[8.7.7.112,16.119,23]hexaeicosa-12,14,16(25),19,21,23(26)-hexene (= F2-[2.1.1]-cryptand) (yield 5%) and 1,13-diaza-28,29-difluoro-4,7,10-trioxatetracyclo[11.7.7.115,19.122,26]nonaeicosa-15,17,19(28),22,24,26(29)-hexene (= F2-[3.1.1]-cryptand) (yield 39%). Analogous reactions of the HF-phane give the related macrocycles HF-[2.1.1]-cryptand (yield 68%) and HF-[3.1.1]-cryptand (yield 76%). The coordination of alkali and alkaline earth metal ions by these fluorophane cryptands results in significant shifts of the 19F NMR resonances: F2-[2.1.1]-cryptand, δ −100.70 ppm; its Li+ complex, δ −129.23 ppm. The 1JCF coupling constant for such complexes is correlated with the degree of interaction between CF units and metal ions, and the most pronounced decrease (262 Hz to 232 Hz) is found for the lithium complex of the F2-[2.1.1]-cryptand. Competition experiments show the difluoro F2-[3.1.1]-cryptand to form significantly stronger complexes with Na+ than the monofluoro HF-[3.1.1]-cryptand. In the crystal structure of F2-[2.1.1]-cryptand·NaCF3SO3, the sodium ion displays an unusual F2O4N coordination sphere with extremely short sodium−fluorine distances: CF···Na+ = 229.8(3), 235.7(4) pm; O−Na+ = 228.5(4), 242.0(4), 243.8(4), 247.6(4) pm; N−Na+ = 285.1(7) pm. In the closely related crystal structure of HF-[3.1.1]-cryptand·NaClO4, the metal has an FO5N coordination sphere: CF···Na+ = 236.0(4) pm; O−Na+ = 234.8(6), 239.3(6), 240.3(12), 240.6(6), 285.7(17) pm; N−Na+ = 272.3(6) pm. In the crystal structure of F2-[3.1.1]-cryptand·HCF3SO3, the proton is in a pseudotetrahedral environment: N−H = 84 pm; O···HN = (216 pm; CF···HN = 224, 236 pm. This, however, is not considered indicative of significant CF···HN hydrogen bonding." @default.
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• W2050871592 date "1997-12-01" @default.
• W2050871592 modified "2023-09-28" @default.
• W2050871592 title "The Coordination Chemistry of Fluorocarbons: Difluoro-<i>m</i>-cyclophane-Based Fluorocryptands and Their Group I and II Metal Ion Complexes" @default.
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• W2050871592 doi "https://doi.org/10.1021/ic9708069" @default.
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