Issue 106, 2005

Hydrogen-bonding, π-stacking and Cl-anion–π interactions of linear bipyridinium cations with phosphate, chloride and [CoCl4]2− anions

Abstract

A series of protonated bipyridinium compounds has been synthesized and their crystal packing is discussed in terms of N–H⋯X contacts (X = O, Cl) together with π–π and Cl⋯π interactions of the positively charged aromatic nitrogen heterocycles. The bipyridinium-anion combinations are diprotonated 4,4′-bipyridin-1,1′-ium bis(dihydrogenphosphate) dihydrate (3), 4,4′-bipyridin-1,1′-ium bis(1,1′-binaphthalene-2,2′-diyl phosphate)·2.5H2O (4), 6,6′-diisoquinolin-2,2′-ium dichloride dihydrate (5), 2,2′-bi-1,6-naphthyridin-6,6′-ium dichloride dihydrate (6) and triprotonated 2,2′-bi-1,6-naphthyridin-1,6,6′-ium-tetrachlorocobaltate(II)-chloride (7). In all structures N+–H hydrogen bonding occurs only to the anion and not to water of crystallization. The packing in 3–6 can be rationalized by a separation of the hydrophobic C–H backbone of the bipyridines from the hydrophilic N–H, phosphate or chloride and water part. N+–H⋯Cl/O hydrogen bonding and π–π-stacking are identified as the major packing interactions in 3–6. In 7 the π-stacking is replaced by remarkably short Cl-anion–π interactions.

Graphical abstract: Hydrogen-bonding, π-stacking and Cl−-anion–π interactions of linear bipyridinium cations with phosphate, chloride and [CoCl4]2− anions

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2005
Accepted
03 Nov 2005
First published
11 Nov 2005

CrystEngComm, 2005,7, 633-641

Hydrogen-bonding, π-stacking and Cl-anion–π interactions of linear bipyridinium cations with phosphate, chloride and [CoCl4]2− anions

T. Dorn, C. Janiak and K. Abu-Shandi, CrystEngComm, 2005, 7, 633 DOI: 10.1039/B508944A

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