engleski

Supramolecular architectures in crystal structures of polycyclic aromatic hydrocarbon-substituted oxalamates

Among noncovalent interactions, hydrogen bonding has been established as effective tool for constructing sophisticated assemblies because of its strength and directionality. Oxalamates are composed of an amide and an ester group directly connected to each other. The N–H, C=O and O–R functionalities allow them to form one-dimensional supramolecular assemblies through intermolecular hydrogen bonding, but they can also form more complex networks whose architectures in the solid state depend on the side-arm substituent(s). Herein, we report on crystal structures of two constitutionally isomeric anthracenesubstituted oxalamates, ethyl N-(1-anthracenyl)oxalamate (1) and ethyl N-(2-anthracenyl)oxalamate (2), with the aim to describe and comparatively discuss the interplay of steric and substitution pattern effects of the oxalamate group at the anthracene ring on the supramolecular organization of the molecules. The position of the oxalamate group resulted in two-dimensional nano-sized networks (for 1 see Figure 1a), built by various supramolecular interactions. In addition, an anthraquinone-derivative 3, the analogue of 1, was studied to probe the effect of the aromatic moiety on the self-assembly process. Indeed, supramolecular structure of 3 is one-dimensional chain (Figure 1b), partially constructed by some intermolecular forces not observed in previous two structures. Acknowledgement. This work has been fully supported by the Croatian Science Foundation under the project IP-2016-06-5983.

supramolecular chemistry ; X-ray diffraction ; oxalamates ; intermolecular interactions

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