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Protonation of Pyruvic Acid – Synthesis of a plain Superelectrophile
Author(s) -
Virmani Alan,
Pfeiffer Martina,
Jessen Christoph,
Morgenstern Yvonne,
Kornath Andreas J.
Publication year - 2022
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.202200005
Subject(s) - protonation , chemistry , crystallography , crystal structure , pyruvic acid , crystal (programming language) , spectroscopy , bond length , nuclear magnetic resonance spectroscopy , molecular geometry , stereochemistry , molecule , medicinal chemistry , ion , organic chemistry , physics , computer science , programming language , quantum mechanics
The syntheses of [H 3 C(O)CC(OH) 2 ][ M F 6 ] and [H 3 C(OH)CC(OH) 2 ][ M F 6 ] 2 ( M= As, Sb) by reacting pyruvic acid in the superacidic systems HF/AsF 5 and HF/SbF 5 are reported. The salts were characterized by low‐temperature vibrational spectroscopy and in the cases of [H 3 C(O)CC(OH) 2 ][SbF 6 ] and [H 3 C(OH)CC(OH) 2 ][SbF 6 ] 2 ⋅ HF by X‐ray crystal structure analyses. The experimental results are discussed together with quantum chemical calculations. Remarkably, the bond distance and the twisting angle around the central C−C bond are unaffected by the protonations despite increasing coulombic repulsion. The crystal structure reveals short interionic interactions that have a considerable influence on the C−C bond.