Structural similarities and diversity in a series of crystalline solids composed of 2-aminopyridines and glutaric acid
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DRAGUTA, Sergiu, FONARI, Marina, BEJAGAM, Shabari Nath, STORMS, Kathryn, LINDLINE, Jennifer, TIMOFEEVA, Tatiana. Structural similarities and diversity in a series of crystalline solids composed of 2-aminopyridines and glutaric acid. In: Structural Chemistry, 2016, nr. 4(27), pp. 1303-1315. ISSN 1040-0400. DOI: https://doi.org/10.1007/s11224-016-0781-2
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Structural Chemistry
Numărul 4(27) / 2016 / ISSN 1040-0400 /ISSNe 1572-9001

Structural similarities and diversity in a series of crystalline solids composed of 2-aminopyridines and glutaric acid
DOI:https://doi.org/10.1007/s11224-016-0781-2

Pag. 1303-1315

Draguta Sergiu1, Fonari Marina12, Bejagam Shabari Nath1, Storms Kathryn1, Lindline Jennifer1, Timofeeva Tatiana1
 
1 New Mexico Highlands University, Las Vegas,
2 Institute of Applied Physics, Academy of Sciences of Moldova
 
 
Disponibil în IBN: 11 august 2022
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 A solvent co-crystallization of three 2-aminopyridine derivatives, 2-aminopyridine (AP), 2-amino-6-methylpyridine (AMP), and 2,6-diaminopyridine (DAP) with the odd-membered propane-1,3-dicarboxylic acid (C5H12O4 = GAH2, glutaric acid) resulted in six ionic crystalline products, (HAP)(GAH) (1), (HAMP)(GAH) (2, 3), (HDAP)(GAH) (4), (HDAP)2(GA) (5), and (HDAP)2(DAP)(GA)(EtOH) (6, EtOH = ethanol). New compounds were characterized by single-crystal and powder X-ray diffraction, melting points, and IR spectra. The proton transfer to the pyridine nitrogen atom in all compounds and the location of H-atom in the carboxylic group in the hydrogen glutarate anion in binary adducts 1–4 was determined reliably from the low-temperature X-ray experiments. All compounds adopt the recurring R2 2(8) 2-aminopyridine–carboxylic acid heteromeric supramolecular synthon. The aggregation of hydrogen glutarate anions in the C(8) chain motifs in 1–4 occurs via the homomeric COOH···COO− robust pattern. Adducts 2 and 3 represent conformational polymorphs; adducts 4, 5 and 6 reveal the diversity in the components’ forms (ionic and neutral), acid–base ratios (1:1, 1:2, and 1:3), and hydrogen-bonding systems. This work demonstrates the variety of forms of glutaric acid in the H-bonded adducts.
Cuvinte-cheie
2-Aminopyridine, Crystal engineering, Glutaric acid, Hydrogen bonds

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<cfAbstr cfLangCode='EN' cfTrans='o'><p>&nbsp;</p><p>A solvent co-crystallization of three 2-aminopyridine derivatives, 2-aminopyridine (AP), 2-amino-6-methylpyridine (AMP), and 2,6-diaminopyridine (DAP) with the odd-membered propane-1,3-dicarboxylic acid (C<sub>5</sub>H<sub>12</sub>O<sub>4</sub>&nbsp;=&nbsp;GAH<sub>2</sub>, glutaric acid) resulted in six ionic crystalline products, (HAP)(GAH) (1), (HAMP)(GAH) (2, 3), (HDAP)(GAH) (4), (HDAP)<sub>2</sub>(GA) (5), and (HDAP)<sub>2</sub>(DAP)(GA)(EtOH) (6, EtOH&nbsp;=&nbsp;ethanol). New compounds were characterized by single-crystal and powder X-ray diffraction, melting points, and IR spectra. The proton transfer to the pyridine nitrogen atom in all compounds and the location of H-atom in the carboxylic group in the hydrogen glutarate anion in binary adducts 1&ndash;4 was determined reliably from the low-temperature X-ray experiments. All compounds adopt the recurring R<sub>2</sub>&nbsp;<sup>2</sup>(8) 2-aminopyridine&ndash;carboxylic acid heteromeric supramolecular synthon. The aggregation of hydrogen glutarate anions in the C(8) chain motifs in 1&ndash;4 occurs via the homomeric COOH&middot;&middot;&middot;COO<sup>&minus;</sup>&nbsp;robust pattern. Adducts 2 and 3 represent conformational polymorphs; adducts 4, 5 and 6 reveal the diversity in the components&rsquo; forms (ionic and neutral), acid&ndash;base ratios (1:1, 1:2, and 1:3), and hydrogen-bonding systems. This work demonstrates the variety of forms of glutaric acid in the H-bonded adducts.</p></cfAbstr>
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