Molecular self assembly of benzene-1,3,5-tricarbonyl phenylalanine

► TMA derivatives of Phe ( 2) and Val ( 3) were studied by NMR, X-ray, TEM and MASS. ► Central aromatic rings in 2 display edge to edge inter-molecular interaction. ► Intermolecular H-bonding, π⋯π and C–H⋯X (π, O, N) interactions support assembly. ► In 2, small crystals are seen at low concentration...

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Bibliographic Details
Published in:Journal of molecular structure 2011-12, Vol.1006 (1), p.180-184
Main Authors: Srinivasulu, Gannoju, Sridhar, Balasubramanian, Ravi Kumar, Krishnan, Sreedhar, Bojja, Ramesh, Venna, Srinivas, Ragampeta, Kunwar, Ajit C.
Format: Article
Language:English
Subjects:
Aggregates
amino acid derivatives
Amino acids
Assembly
CH–X (π, O, N) interactions
Derivatives
H-bonding
Hydrogen bonding
Molecular self assembly
Molecular structure
Phenylalanine
Self assembly
π–π Stacking
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Summary:► TMA derivatives of Phe ( 2) and Val ( 3) were studied by NMR, X-ray, TEM and MASS. ► Central aromatic rings in 2 display edge to edge inter-molecular interaction. ► Intermolecular H-bonding, π⋯π and C–H⋯X (π, O, N) interactions support assembly. ► In 2, small crystals are seen at low concentration and fibrils at high concentration. Benzene-1,3,5-tricarboxylic acid derivatives with amino acids have a strong tendency to aggregate in solution. In the present communication we report a detailed study of the self assembly of these derivatives containing Phe and Val. Intermolecular hydrogen bonding, π⋯π and weak C–H⋯X (X = π, O, N) interactions are involved in the process of molecular assembly.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2011.09.006