期刊
CRYSTENGCOMM
卷 19, 期 37, 页码 5576-5582出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ce01332a
关键词
-
资金
- Croatian Science Foundation [IP-2014-09-7367]
In this work, we describe novel halogen bonded o-vanillin imine cocrystals. As cocrystal coformers, we selected perfluorinated diiodobenzenes, 1,2-, 1,3- and 1,4-diiodotetrafluorobenzene, as halogen bond donors. To explore the halogen bonding proclivity of the o-vanillin ortho-methoxy-hydroxy group, two imines were produced by condensation of o-vanillin with amines containing hydrophobic residues that have no additional potential halogen bond acceptor sites other than the o-vanillin oxygen atoms. We have prepared four cocrystals by both one-pot three- component solvent-free synthesis and the conventional solution-based method. The results of our work show that the ortho-methoxy-hydroxy group of the o-vanillin moiety is a good halogen bond acceptor and is capable of forming predictable halogen-bonded synthons. In the studied cocrystal structures, a wide range of varieties of this synthon were observed, including bonds with a single acceptor (either the methoxy O atom - in two structures, or the hydroxy O atom - in one), 'slightly bifurcated' bonds with a dominant (hydroxy) and ancillary (methoxy) acceptor, and a geometrically unusual asymmetrical bifurcated bond.
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