NDLI: Investigation of supramolecular synthons and structural characterisation of aminopyridine-carboxylic acid derivatives

Content Provider	Springer Nature : BioMed Central
Author	Hemamalini, Madhukar Loh, Wan-Sin Quah, Ching Kheng Fun, Hoong-Kun
Abstract	Background Co-crystal is a structurally homogeneous crystalline material that contains two or more neutral building blocks that are present in definite stoichiometric amounts. The main advantage of co-crystals is their ability to generate a variety of solid forms of a drug that have distinct physicochemical properties from the solid co-crystal components. In the present investigation, five co-crystals containing 2-amino-6-chloropyridine (AMPY) moiety were synthesized and characterized. Results The crystal structure of 2-amino-6-chloropyridine (AMPY) (I), and the robustness of pyridine-acid supramolecular synthon were discussed in four stoichiometry co-crystals of AMPY…BA (II), AMPY…2ABA (III), AMPY…3CLBA (IV) and AMPY…4NBA (V). The abbreviated designations used are benzoic acid (BA), 2-aminobenzoic acid (2ABA), 3-chlorobenzoic acid (3CLBA) and 4-nitrobenzoic acid (4NBA). All the crystalline materials have been characterized by 1HNMR, 13CNMR, IR, photoluminescence, TEM analysis and X-ray diffraction. The supramolecular assembly of each co-crystal is analyzed and discussed. Conclusions Extensive N---H · · · N/N---H · · · O/O---H · · · N hydrogen bonds are found in (I-V), featuring different supramolecular synthons. In the crystal structure, for compound (I), the 2-amino-6-chloropyridine molecules are linked together into centrosymmetric dimers by hydrogen bonds to form homosynthon, whereas for compounds (II-V), the carboxylic group of the respective acids (benzoic acid, 2-aminobenzoic acid, 3-chlorobenzoic acid and 4-nitrobenzoic acid) interacts with pyridine molecule in a linear fashion through a pair of N---H · · · O and O---H · · · N hydrogen bonds, generating cyclic hydrogen-bonded motifs with the graph-set notation R 2 2 8 , to form heterosynthon. In compound (II), another intermolecular N---H · · · O hydrogen bonds further link these heterosynthons into zig-zag chains. Whereas in compounds (IV) and (V), these heterosynthons are centrosymmetrically paired via N---H · · · O hydrogen bonds and each forms a complementary DADA [D = donor and A = acceptor] array of quadruple hydrogen bonds, with graph-set notation R 2 3 8 , R 2 2 8 and R 2 3 8 .
Related Links	https://bmcchem.biomedcentral.com/counter/pdf/10.1186/1752-153X-8-31.pdf
Ending Page	9
Page Count	9
Starting Page	1
File Format	HTM / HTML
DOI	10.1186/1752-153X-8-31
Journal	BMC Chemistry
Issue Number	1
Volume Number	8
Language	English
Publisher	BioMed Central
Publisher Date	2014-05-06
Access Restriction	Open
Subject Keyword	Chemistry Food Science Benzoic Acid Transmission Electron Micrographs Cambridge Crystallographic Data Centre Hydrogen Bond Geometry Supramolecular Synthons Chemistry/Food Science
Content Type	Text
Resource Type	Article
Subject	Chemistry
Journal Impact Factor	4.3/2023
5-Year Journal Impact Factor	4.4/2023

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