164655-83-8Relevant academic research and scientific papers
Host-Enhanced Phenyl-Perfluorophenyl Polar-πInteractions
Huang, Zehuan,Chen, Xiaoyi,Wu, Guanglu,Metrangolo, Pierangelo,Whitaker, Daniel,McCune, Jade A.,Scherman, Oren A.
, p. 7356 - 7361 (2020)
Phenyl-perfluorophenyl polar-πinteractions have been revisited for the design and fabrication of functional supramolecular systems. The relatively weak associative interactions (ΔG ≈ -1.0 kcal/mol) have limited their use in aqueous self-assembly to date.
Synthetic and structural studies on pentafluorobenzylated imidazole systems
Lampl, Martin,Schlapp-Hackl, Inge,Wurst, Klaus,Gelbrich, Thomas,Kopacka, Holger,Müller, Thomas,Kreutz, Christoph,Naier, Benjamin,Partl, Gabriel Julian,Kahlenberg, Volker,Amer, Hassan,Bacher, Markus,Rosenau, Thomas,Huppertz, Hubert,Schottenberger, Herwig
, p. 51 - 62 (2018/12/11)
Quaternization of common N-functionalized imidazoles (vinyl-, allyl-, propargyl-) with pentafluorobenzyl bromide afforded the respective series of differently substituted imidazolium salts. Likewise, chemospecific S- and N-alkylation of the commercial med
Single-crystal X-ray diffraction and solution studies of anion-π interactions in N-(pentafluorobenzyl)pyridinium salts
Giese, Michael,Albrecht, Markus,Repenko, Tatjana,Sackmann, Johannes,Valkonen, Arto,Rissanen, Kari
, p. 2435 - 2442 (2014/05/06)
A solid-state structural study on anion-π interaction in various N-(pentafluorobenzyl)pyridinium salts accompanied by NMR spectroscopic investigations is presented. The crystal structures of 1a-1d reveal different kinds of contacts with anions, including anion-π interactions. In particular, the solid-state structure of 1b-I3 shows distinct evidence of anion-π interactions. Attempts to study anion-π interactions in solution were not successful, but their presence in solution could not be ruled out. The interactions of N-(pentafluorobenzyl)pyridinium salts are investigated in the solid state as well as in solution. The triiodide salt shows distinct evidence of anion-π interactions with both the pyridinium and the pentafluorophenyl unit. Solution investigations to prove the attractive nature of the noncovalent force failed, but they did not rule out the presence of the interaction. Copyright
Anion-Binding Catalysis by Electron-Deficient Pyridinium Cations
Berkessel, Albrecht,Das, Somnath,Pekel, Daniel,Neud?rfl, J?rg-M.
supporting information, p. 11660 - 11664 (2016/02/18)
A new activation principle in organocatalysis is presented: halide binding through Coulombic interactions. This mode of catalysis was realized by using 3,5-di(carbomethoxy)pyridinium ions that carry an additional electron-withdrawing substituent on the nitrogen atom, for example, pentafluorobenzyl or cyanomethyl. For the N-pentafluorobenzyl derivative, Coulombic interaction with the pyridinium moiety is complemented in the solid state by anion-π interactions with the perfluorophenyl ring. Bromide and chloride are bound by these cations in a 1:1 stoichiometry. Catalysis of the C-C coupling between 1-chloroisochroman (and related electrophiles) with silyl ketene acetals occurs at -78 °C and at low catalyst loading (2 mol %).
