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

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Title:Self-Assembly of 1,1'-Biphenyl-2,2',6,6'-tetracarboxamides. Effect of Substitution at the Amidic Nitrogen
Creators:
Holý, Petr
Podlaha, Jaroslav
Císařová, Ivana
Závada, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 6, pp. 947-958
Uncontrolled Keywords:Biaryls, Solid state self-assembly, X-Ray diffraction, Crystal structure determination, Crystal engineering, Biphenyls, Supramolecular structures, Amides, Hydrogen bonds

Abstract

Self-assembly of three 1,1'-biphenyl-2,2',6,6'-tetracarboxamides <strong>2a</strong>-<strong>2c</strong> differing each from the other by substitution at the amidic nitrogens (R = H, ethyl and 1-(<i>R</i>)-phenylethyl, respectively) was investigated by single crystal X-ray diffraction analysis. It was found that the unsubstituted tetracarboxamide <strong>2a</strong> gives rise to infinite hydrogen-bonded 2D network composed from chiral cyclotetrameric squares (D<sub>4</sub> symmetry). Such self-assembling pattern is suppressed by alkyl substitution in <strong>2b</strong> and <strong>2c</strong>, which disfavours formation of intermolecular amide-amide hydrogen bonds. <p>

Title:Self-Assembly of 1,1'-Biphenyl-2,2',6,6'-tetracarboxamides. Effect of Substitution at the Amidic Nitrogen
Creators:
Holý, Petr
Podlaha, Jaroslav
Císařová, Ivana
Závada, Jiří
Uncontrolled Keywords:Biaryls, Solid state self-assembly, X-Ray diffraction, Crystal structure determination, Crystal engineering, Biphenyls, Supramolecular structures, Amides, Hydrogen bonds
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:66
Number:6
Page Range:pp. 947-958
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20010947UNSPECIFIED
ID Code:1834
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Holý, Petr; Podlaha, Jaroslav; Císařová, Ivana; Závada, Jiří (2001) Self-Assembly of 1,1'-Biphenyl-2,2',6,6'-tetracarboxamides. Effect of Substitution at the Amidic Nitrogen. Collection of Czechoslovak Chemical Communications, 66 (6). pp. 947-958. ISSN 0010-0765

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