2-Aminopyridinium–succinate–succinic acid (2/1/1)

Büyükgüngör, Orhan; ̨ogˇlu, Mustafa Odabas

doi:10.1107/s0108270102017808

Cited by 12 publications

(1 citation statement)

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“…This is further supported by the C5—N2—H1N2/H2N2 angles which are in the range of 115.1-120.0° and the fact that atoms C5, N2, H1N2 and H2N2 lie almost in the pyridine plane. Similar bond distances and angles have been observed in 2-aminopyridinium succinate-succinic acid [15]. Proton transfer does not take place from the carboxylic acid to the N atom of 2-amino-6-chloropyridine ring, and the internal C1—N1—C5 angles are 116.8 (1)° (I) , 117.1 (2)° (II) , 116.…”

Section: Resultssupporting

confidence: 69%

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

Hemamalini

Loh

Quah

et al. 2014

Chemistry Central Journal

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BackgroundCo-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.ResultsThe 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.ConclusionsExtensive 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 notationR228, 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 R238, italicR228 and italicR238.

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Section: Resultssupporting

confidence: 69%