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• W2317372450 endingPage "7984" @default.
• W2317372450 startingPage "7975" @default.
• W2317372450 abstract "We report detailed studies on the characterization of an intramolecular NH-F hydrogen bond formed within a fluorinated proton sponge derivative. An ammonium ion, generated from 8-fluoro-N,N-dimethylnaphthalen-1-amine, serves as a charged hydrogen bond donor to a covalently bound fluorine appropriately positioned on the naphthalene skeleton. Potentiometric titrations of various N,N-dimethylnaphthalen-1-amines demonstrate a significant increase in basicity when hydrogen bonding is possible. X-ray crystallography reveals that NH-F hydrogen bonding in protonated 8-fluoro-N,N-dimethylnaphthalen-1-amine is heavily influenced by ion pairing in the solid state; bifurcated and trifurcated hydrogen bonds are formed depending on the counterion utilized. Compelling evidence of hydrogen bonding in the 8-fluoro-N,N-dimethylnaphthyl-1-ammonium cation is provided by gas-phase cryogenic vibrational photodissociation spectroscopy. Solution-phase infrared spectroscopy provides complementary results, and the frequencies of the N-H stretching mode in both phases are in excellent agreement with the computed vibrational spectra. NMR analysis of protonated 8-fluoro-N,N-dimethylnaphthalen-1-amine demonstrates significant H-F coupling between the N-H hydrogen and fluorine that cannot be attributed to long-range, through-bond interactions; the couplings correlate favorably with calculated values. The results obtained from these experiments are congruent with the formation of an NH-F hydrogen bond upon protonation of 8-fluoro-N,N-dimethylnaphthalen-1-amine." @default.
• W2317372450 created "2016-06-24" @default.
• W2317372450 creator A5003933674 @default.
• W2317372450 creator A5005123295 @default.
• W2317372450 creator A5013096298 @default.
• W2317372450 creator A5022283101 @default.
• W2317372450 creator A5031623363 @default.
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• W2317372450 creator A5061141556 @default.
• W2317372450 creator A5080411108 @default.
• W2317372450 creator A5087375367 @default.
• W2317372450 date "2011-09-02" @default.
• W2317372450 modified "2023-09-29" @default.
• W2317372450 title "NH⁺–F Hydrogen Bonding in a Fluorinated “Proton Sponge” Derivative: Integration of Solution, Solid-State, Gas-Phase, and Computational Studies" @default.
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• W2317372450 doi "https://doi.org/10.1021/jo2015328" @default.
• W2317372450 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/21888333" @default.

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