Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Interactions in Crystals. 136. Protonated Dipyridylamine Salts with Different Anions: Monomeric Tetraphenylborate as well as Bis(trifluormethylsulfonate), Dimeric Squarate and Polymeric Chloride DihydrateDi(pyrid-2-yl)amine is monoprotonated by acetic, squaric as well as hydrochloric acid and diprotonated by trifluoromethylsulfonic acid. To explore the anion and hydrogen-bridge dependency of its salts, crystals of the monomeric tetraphenylborate, the dimeric squarate as well as the bis(trifluoromethylsulfonate) and the polymeric chloride hydrate have been grown and their structures determined: Separated by bulky tetraphenylborate anions, pyrid-2-yl(2′-pyridinium) amine cation contains an intramolecular hydrogen bridge N⊕H…N and is slightly folded. The squarate salt dimer exhibits additional bridges, N—H…O⊖ and O—H…O. The severely twisted di(2-pyridinium)amine dication is connected to its trifluormethylsulfonate counter anions by altogether three H-bridges, two N⊕H…O and one N—H…O. The chloride dihydrate crystallizes in layers of 16-membered rings, formed from three Cl anions and five water molecules. The diversity of the hydrogen-bridge dominated salt structures is discussed based on comparison with selected literature examples and on PM3 calculations.
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