Journal
CRYSTENGCOMM
Volume 15, Issue 16, Pages 3125-3136Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ce26747k
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Funding
- NSF [CHE-0957607]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0957607] Funding Source: National Science Foundation
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In order to study the structure-directing competition between hydrogen-and halogen-bond donors we have synthesized two ligands, 3,3'-azobipyridine and 4,4'-azobipyridine, and co-crystallized them with a series of bi-functional donor molecules comprising an activated halogen-bond donor (I or Br) as well as a hydrogen-bond donor (acid, phenol or oxime) on the same backbone. Based on the subsequent single-crystal analysis, 5 of 6 co-crystals of 3,3'-azobipyridine are assembled using hydrogen bonds as the primary driving force accompanied by weaker secondary (C-X center dot center dot center dot O) interactions. However, in 5 out of the 6 cocrystals of 4,4'-azobipyridine, both hydrogen bonds (O-H center dot center dot center dot N) and halogen bonds (C-X center dot center dot center dot N) are present as structure-directing interactions leading to 1-D chains. Since the charges on the acceptor sites in 3,3'- and 4,4'-azobipyridine are very similar, the observed difference in binding behaviour highlights the importance of binding-site location on the acceptor molecules (anti-parallel in 3,3'-azobipyridine and co-linear in 4,4'-azobipyridine) as a direct influence over the structural balance between hydrogen-and halogen-bond donors.
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