Collect. Czech. Chem. Commun. 2001, 66, 947-958

Self-Assembly of 1,1'-Biphenyl-2,2',6,6'-tetracarboxamides. Effect of Substitution at the Amidic Nitrogen

Petr Holýa, Jaroslav Podlahab, Ivana Císařováb and Jiří Závadaa,*

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
b Department of Inorganic Chemistry, Charles University, 128 40 Prague 2, Czech Republic


Self-assembly of three 1,1'-biphenyl-2,2',6,6'-tetracarboxamides 2a-2c differing each from the other by substitution at the amidic nitrogens (R = H, ethyl and 1-(R)-phenylethyl, respectively) was investigated by single crystal X-ray diffraction analysis. It was found that the unsubstituted tetracarboxamide 2a gives rise to infinite hydrogen-bonded 2D network composed from chiral cyclotetrameric squares (D4 symmetry). Such self-assembling pattern is suppressed by alkyl substitution in 2b and 2c, which disfavours formation of intermolecular amide-amide hydrogen bonds.

Keywords: Amides; Crystal structure determination; Hydrogen bonds; X-Ray diffraction; Crystal engineering; Solid state self-assembly; Biaryls; Biphenyls; Supramolecular structures.

References: 19 live references.