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Superacidic or Not…︁? Synthesis, Characterisation, and Acidity of the Room‐Temperature Ionic Liquid [C(CH 3 ) 3 ] + [Al 2 Br 7 ] −
Author(s) -
Scholz Franziska,
Himmel Daniel,
Scherer Harald,
Krossing Ingo
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203260
Subject(s) - chemistry , bromide , raman spectroscopy , inorganic chemistry , sulfuric acid , cationic polymerization , ionic liquid , ionic bonding , protonation , reactivity (psychology) , brønsted–lowry acid–base theory , lewis acids and bases , ion , organic chemistry , catalysis , medicine , physics , alternative medicine , pathology , optics
The room‐temperature ionic liquid (RT‐IL) [C(CH 3 ) 3 ] + [Al 2 Br 7 ] − (m.p. 2 °C) was generated by bromide abstraction from tert ‐butyl bromide with the Lewis acid aluminum bromide in the absence of solvent. The crystal structure of the tert ‐butyl cation salt was determined by X‐ray diffraction. NMR, IR, and Raman spectroscopy, as well as quantum‐chemical and thermodynamic calculations, confirm the composition of this RT‐IL. Thus, one may consider this RT‐IL to be a readily accessible (and on a large scale) cationic Brønsted acid (protonated isobutene) with the potential for further reactivity. Based on the new absolute Brønsted acidity scale, we calculated an absolute pH abs value of 171 for liquid bulk [C(CH 3 ) 3 ] + [Al 2 Br 7 ] − . This value is about as acidic as 100 % sulfuric acid (pH abs =171) and, thus, on the edge of superacidity.