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The importance of weak C-H center dot center dot center dot O bonds and pi center dot center dot center dot pi stacking interactions in the formation of organic 1,8-bis(dimethylamino)naphthalene complexes with Z '> 1

Lookup NU author(s): Gary Nichol, Emeritus Professor Bill CleggORCiD


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Reaction in methanol or water of the organic base 1,8-bis(dimethylamino)naphthalene (often called "proton sponge", PS) with four simple chemically related organic acids (HA), namely, violuric acid (VIH), cyanuric acid (CYH), barbituric acid (BAH), and orotic acid (ORH), gave rise to four new organic salts, 1-4, respectively, with very different crystal structures. Crystallographic problems (including disorder, weak diffraction, and rapid dissolution at ambient temperatures) were encountered with all four compounds and were successfully resolved in each case. Analysis of the crystal packing shows that weak C-H... 0 and stacking interactions are important in maintaining the integrity of the structures. All four compounds have asymmetric units containing more than a single ion pair PSH+A(-) (i.e., Z" > 2)-, for the chemically simple compound PS(+)Vl(-)center dot MeOH (1), Z' 1 and Z" = 3, but for the more complicated compound PS+OR- (4), Z = 8 and Z' = 16 (counting only the species that have been modeled with discrete atoms and ignoring others that are highly disordered in "voids" of the structure) with an extensive network of weak intermolecular interactions holding the structure together.

Publication metadata

Author(s): Nichol GS, Clegg W

Publication type: Review

Publication status: Published

Journal: Crystal Growth & Design

Year: 2006

Volume: 6

Issue: 2

Pages: 451-460

ISSN (print): 1528-7483

ISSN (electronic): 1528-7505

URL: .http//

DOI: 10.1021/cg0503806