ISSN:
1434-193X
Keywords:
Di(2-pyridyl) ketone
;
Single and twofold protonation
;
Crystal structures of tetraphenylborate and chloride salts
;
Tetraphenylborates
;
Chlorides
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Di(2-pyridyl) ketone, intricately twisted due to its two nNσ and one nOσ lone pairs, exhibits tremendous structural differences on single and double protonation to salts containing either the anion [B(C6H5)4]-, which cannot be protonated, or Cl-, which accepts two hydrogen bonds. In the monocation, generated in acetic acid with added sodium tetraphenylborate, the pyridine rings of di(2-pyridyl) ketone are planarized due to the formation of an intermolecular hydrogen bond. Aqueous hydrogen chloride produces a dication with both nitrogen centers protonated and the resulting di(2-pyridyl) ketone hydrate embedded in a complex hydrogen-bond network. Extensive quantum-chemical calculations based on the experimental structural data allow to rationalize the unexpected results.
Type of Medium:
Electronic Resource
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