Reaction of the 1,8-bis(diphenylmethylium)naphthalenediyl dication with fluoride: formation of a cation containing a C-F-->C bridge

Journal of the American Chemical Society
Huadong WangFrançois P Gabbaï

Abstract

Treatment of 1,8-bis(diphenylhydroxymethyl)naphthalene with a mixture of [HBF(4)](aq) and (CF(3)CO)(2)O affords the corresponding dication, 1,8-bis(diphenylmethylium)naphthalenediyl (1(2+)), which was isolated as the [BF4]- salt. This dication has been fully characterized, and its structure has been studied computationally. The (13)C NMR resonance of the methylium centers appears at 207.7 ppm. As indicated by an X-ray single-crystal analysis, the vicinal methylium centers are separated by 3.112(4) A. Dication (1(2+)) reacts with fluoride to afford [1-F]+ which has been isolated as the [BF4]- salt. The fluorine atom of [1-F](+) is connected to one of the former methylium centers through a typical C-F bond of 1.424(2) A and forms a long interaction of 2.444(2) A with the other methylium center. While the structure of [1-F]+ can be largely accounted for by considering a simple methylium formulation, density functional calculations followed by an Atom In Molecules analysis as well as a calculation of the Boys localized orbitals indicate that the long C-F interaction of 2.444(2) A corresponds to a dative bond. Hence, formulation of [1-F]+ as an unsymmetrical fluoronium must also be considered. As indicated by 1H NMR spectroscopy, th...Continue Reading

References

Jul 17, 2003·Angewandte Chemie·Christelle HerseJérôme Lacour
Oct 24, 2003·Environmental Science & Technology·M AslamMartha J Shearer
Dec 26, 2003·Angewandte Chemie·Huadong Wang, François P Gabbaï
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Citations

May 8, 2013·Proceedings of the National Academy of Sciences of the United States of America·George A OlahGolam Rasul
Apr 6, 2013·Science·Mark D StrubleThomas Lectka
Jun 21, 2017·Chemical Communications : Chem Comm·Ian MallovDouglas W Stephan
Jan 10, 2018·Angewandte Chemie·Cody Ross PittsThomas Lectka
Sep 10, 2009·Angewandte Chemie·Mathias LehmannAlexander Villinger
Nov 22, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Takanori SuzukiKenshu Fujiwara
Sep 22, 2019·Angewandte Chemie·Lewis C WilkinsFrançois P Gabbaï
May 13, 2010·Chemistry : a European Journal·Axel Schulz, Alexander Villinger
Jul 26, 2017·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Kantapat ChansaenpakFrançois P Gabbaï
Apr 1, 2009·Chemical Reviews·Hideki Amii, Kenji Uneyama
Jul 7, 2005·Journal of the American Chemical Society·Terunobu Saitoh, Junji Ichikawa
Jan 14, 2005·Organic Letters·Huadong Wang, François P Gabbaï
Jul 28, 2020·Journal of the American Chemical Society·Mohammadjavad KarimiFrançois P Gabbaï
Nov 3, 2011·The Journal of Organic Chemistry·Sean P McClintock, Nancy S Mills
Dec 27, 2019·Accounts of Chemical Research·Maxwell Gargiulo HollThomas Lectka
Sep 8, 2021·Nature Communications·Kurt F HoffmannSebastian Riedel
Jul 27, 2006·Journal of the American Chemical Society·Robin PanischThomas Müller
Jun 21, 2008·Chemical Reviews·Jun-ichi YoshidaAiichiro Nagaki

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