Helical Assembly Induced by Hydrogen Bonding from Chiral Carboxylic Acids Based on Perylene Bisimides

2011 ◽  
Vol 115 (37) ◽  
pp. 10871-10876 ◽  
Author(s):  
Xinyu Lu ◽  
Zhiqian Guo ◽  
Chunyu Sun ◽  
He Tian ◽  
Weihong Zhu
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acids ◽  
Perylene Bisimides

Hydrogen Bonding and Ionization of Carboxylic Acids in Aqueous Solutions

1951 ◽  
Vol 73 (12) ◽  
pp. 5889-5890 ◽  
Author(s):  
A. Katchalsky ◽  
H. Eisenberg ◽  
S. Lifson
Keyword(s):  
Hydrogen Bonding ◽  
Aqueous Solutions ◽  
Carboxylic Acids

Solvent-mediated pseudo-quadruple hydrogen-bond motifs in three lamotrigine–carboxylic acid complexes

2013 ◽  
Vol 69 (10) ◽  
pp. 1164-1169 ◽  
Author(s):  
Balasubramanian Sridhar ◽  
Jagadeesh Babu Nanubolu ◽  
Krishnan Ravikumar
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Proton Transfer ◽  
Antiepileptic Drug ◽  
Carboxylic Acids ◽  
Solvent Interactions ◽  
Partial Transfer ◽  
Quadruple Hydrogen Bonding ◽  
Quadruple Hydrogen Bond

Lamotrigine, an antiepileptic drug, has been complexed with three aromatic carboxylic acids. All three compounds crystallize with the inclusion ofN,N-dimethylformamide (DMF) solvent,viz.lamotriginium [3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium] 4-iodobenzoateN,N-dimethylformamide monosolvate, C9H8Cl2N5+·C7H4IO2−·C3H7NO, (I), lamotriginium 4-methylbenzoateN,N-dimethylformamide monosolvate, C9H7Cl2N5+·C8H8O2−·C3H7NO, (II), and lamotriginium 3,5-dinitro-2-hydroxybenzoateN,N-dimethylformamide monosolvate, C9H8Cl2N5+·C7H3N2O7−·C3H7NO, (III). In all three structures, proton transfer takes place from the acid to the lamotrigine molecule. However, in (I) and (II), the acidic H atom is disordered over two sites and there is only partial transfer of the H atom from O to N. In (III), the corresponding H atom is ordered and complete proton transfer has occurred. Lamotrigine–lamotrigine, lamotrigine–acid and lamotrigine–solvent interactions are observed in all three structures and they thereby exhibit isostructurality. The DMF solvent extends the lamotrigine–lamotrigine dimers into a pseudo-quadruple hydrogen-bonding motif.

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