Hydrogen Bonding and Stacking π−π Interactions in Solid 6-Thioguanine and 6-Mercaptopurine (Antileukemia and Antineoplastic Drugs) Studied by NMR-NQR Double Resonance Spectroscopy and Density Functional Theory

2009 ◽  
Vol 113 (30) ◽  
pp. 8781-8790 ◽  
Author(s):  
J. N. Latosińska ◽  
J. Seliger ◽  
V. Žagar ◽  
D. V. Burchardt
Keyword(s):  
Density Functional Theory ◽  
Hydrogen Bonding ◽  
Density Functional ◽  
Double Resonance ◽  
Resonance Spectroscopy ◽  
Antineoplastic Drugs ◽  
Functional Theory ◽  
Π Interactions ◽  
Double Resonance Spectroscopy

Hydrogen bonding in two benzene-1,2-diaminium pyridine-2-carboxylate salts and a cocrystal of benzene-1,2-diamine and benzoic acid

2019 ◽  
Vol 75 (3) ◽  
pp. 329-335 ◽  
Author(s):  
Kyle A. Powers ◽  
David K. Geiger
Keyword(s):  
Density Functional Theory ◽  
Hydrogen Bonding ◽  
Benzoic Acid ◽  
Intermolecular Interactions ◽  
Density Functional ◽  
Salt Formation ◽  
Functional Theory ◽  
Π Interactions ◽  
Fingerprint Plot

The isostructural salts benzene-1,2-diaminium bis(pyridine-2-carboxylate), 0.5C6H10N2 2+·C6H4NO2 −, (1), and 4,5-dimethylbenzene-1,2-diaminium bis(pyridine-2-carboxylate), 0.5C8H14N2 2+·C6H4NO2 −, (2), and the 1:2 benzene-1,2-diamine–benzoic acid cocrystal, 0.5C6H8N2·C7H6O2, (3), are reported. All of the compounds exhibit extensive N—H...O hydrogen bonding that results in interconnected rings. O—H...N hydrogen bonding is observed in (3). Additional π–π and C—H...π interactions are found in each compound. Hirshfeld and fingerprint plot analyses reveal the primary intermolecular interactions and density functional theory was used to calculate their strengths. Salt formation by (1) and (2), and cocrystallization by (3) are rationalized by examining pK a differences. The R 2 2(9) hydrogen-bonding motif is common to each of these structures.

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