scholarly journals Structure-Making with 3,5-Dinitrosalicylic Acid. II. The Proton-Transfer Compounds of 3,5-Dinitrosalicylic Acid with the Monocyclic Heteroaromatic Amines

2003 ◽  
Vol 56 (7) ◽  
pp. 707 ◽  
Author(s):  
Graham Smith ◽  
Urs D. Wermuth ◽  
Peter C. Healy ◽  
Jonathan M. White
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Nitrogen Atom ◽  
Proton Transfer ◽  
Crystal Structures ◽  
Functional Groups ◽  
Chain Polymer ◽  
Proton Transfer Compounds ◽  
Oxygen Atoms

The crystal structures of the proton-transfer compounds of 3,5-dinitrosalicylic acid (dnsa) with a series of common monocyclic heteroaromatic amines (pyridine, 4-cyanopyridine, pyridine-4-carboxylic acid, 2,6-diaminopyridine, and 2-aminopyrimidine) have been determined and the hydrogen-bonding associations in each analyzed. The compounds are the adduct [(C5H6N)+(dnsa)–· (dnsa)] (1), the 1 : 1 salts [(C6H5N2)+(dnsa)–] (2), [(C6H6NO2)+(dnsa)–] (3), [(C5H8N3)+(dnsa)–] (4), and the 2 : 2 ethanol hemi-solvate [2(C4H6N3)+·2(dnsa)–· 0.5(EtOH)] (5). With all compounds, protonation of the hetero-nitrogen atom occurs with subsequent hydrogen bonding to the oxygen atoms of the functional groups of the dnsa anions, resulting in the formation of relatively simple linear or chain polymer associations. Compound (1) represents a rare example of other than a 1 : 1 association, and the first example of a 2 : 1 (dnsa/amine) type, with the unusual presence of an additional adduct molecule of dnsa in the structure.

scholarly journals 3,5-Dinitrosalicylic Acid in Molecular Assembly. III. Proton-Transfer Compounds of 3,5-Dinitrosalicylic Acid with Polycyclic Aromatic and Heteroaromatic Amines, and Overall Series Structural Systematics

2007 ◽  
Vol 60 (4) ◽  
pp. 264 ◽  
Author(s):  
Graham Smith ◽  
Urs D. Wermuth ◽  
Peter C. Healy ◽  
Jonathan M. White
Keyword(s):  
Hydrogen Bonding ◽  
Proton Transfer ◽  
Crystal Structures ◽  
Molecular Assembly ◽  
Lewis Base ◽  
Amino Group ◽  
Π Interactions ◽  
Hydrogen Donors ◽  
Polycyclic Aromatic ◽  
Proton Transfer Compounds

The crystal structures of the 1:1 proton-transfer compounds of 3,5-dinitrosalicylic acid (dnsa) with a series of common polycyclic aromatic and heteroaromatic amines (quinoline, 1-naphthylamine, 1,2,3,4-tetrahydroquinoline, quinaldic acid, benzimidazole, 1,10-phenanthroline, and 2,2′-bipyridine) have been determined and the hydrogen-bonding associations in each analyzed. The compounds are [(C9H8N)+(dnsa)–] 1, [(C10H10N)+(dnsa)–] 2, [(C9H12N)+(dnsa)–] 3, [(C10H8NO2)+(dnsa)–] 4, [(C7H7N2)+(dnsa)–] 5, [(C12H9N2)+(dnsa)–] 6, and [(C10H9N2)+(dnsa)–] 7. In all compounds, protonation of either the substituent amino group or the hetero-N of the Lewis base occurs, with subsequent hydrogen bonding via this and other hydrogen donors variously to the carboxylate, phenate, and nitro oxygen acceptors of the dnsa anions. The result is the formation of primary N+–H···O associations which with secondary peripheral interactions, which within this set of compounds includes an increased incidence of aromatic C–H···O associations, give framework polymer structures. In three of the compounds [1, 4, and 6], cation–anion π–π interactions are also found. The completion of this series of compounds has now allowed the categorization of the molecular assembly modes in the proton-transfer compounds of 3,5-dinitrosalicylic acid.

scholarly journals A computational study on how structure influences the optical properties in model crystal structures of amyloid fibrils

2017 ◽  
Vol 19 (5) ◽  
pp. 4030-4040 ◽  
Author(s):  
Luca Grisanti ◽  
Dorothea Pinotsi ◽  
Ralph Gebauer ◽  
Gabriele S. Kaminski Schierle ◽  
Ali A. Hassanali
Keyword(s):  
Optical Properties ◽  
Hydrogen Bonding ◽  
Proton Transfer ◽  
Crystal Structures ◽  
Amyloid Fibrils ◽  
Computational Study ◽  
Model Systems ◽  
Hydrogen Bonding Interactions ◽  
Model Crystal ◽  
Different Types

Different types of hydrogen bonding interactions that occur in amyloids model systems and molecular factors that control the susceptibility of the protons to undergo proton transfer and how this couples to the optical properties.

Hydrogen bonding networks and proton transfer compounds of cobalt(II) and copper(II) with pyridine-2,5-dicarboxylate

Polyhedron ◽  
2011 ◽  
Vol 30 (6) ◽  
pp. 1012-1022 ◽  
Author(s):  
Alper Tolga Çolak ◽  
Okan Zafer Yeşilel ◽  
Gönül Pamuk ◽  
Handan Günay ◽  
Orhan Büyükgüngör
Keyword(s):  
Hydrogen Bonding ◽  
Proton Transfer ◽  
Hydrogen Bonding Networks ◽  
Proton Transfer Compounds

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.

Inhibitors of the geotropic response in plants. The crystal structures of 2-[(Naphthalen-2-yl)carbamoyl]benzoic acid (β-Naptalam), 2-(Phenylcarbamoyl)-benzoic acid and 2-(5-Phenyl-1,3,4-oxadiazol-2-yl)benzoic acid

1983 ◽  
Vol 36 (12) ◽  
pp. 2455 ◽  
Author(s):  
G Smith ◽  
CHL Kennard ◽  
GF Katekar
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Benzoic Acid ◽  
Crystal Structures ◽  
Carboxylic Acids ◽  
Intermolecular Hydrogen Bonding ◽  
X Ray Diffraction ◽  
X Ray ◽  
Carboxylic Acid Groups ◽  
Phthalamic Acid

The crystal structures of three geotropically active phthalamic acid derivatives have been determined by means of X-ray diffraction and the structural systematics for the series compared. The three acids are conformationally similar and, in contrast to the tendency among carboxylic acids to form hydrogen-bonded dimers, they exist as monomers with intermolecular hydrogen bonding between the carboxylic acid groups and the nitrogen or oxygen of the amide side chains.

The hydrogen-bonded complex bis(tert-butylammonium) 2,6-dichlorophenolate 2,4-dichlorophenol–2,4-dichlorophenolate tetrahydrofuran disolvate containing a chiralR53(10) hydrogen-bonded ring as a supramolecular synthon

2016 ◽  
Vol 72 (10) ◽  
pp. 720-723 ◽  
Author(s):  
Xiao-Qing Cai ◽  
Bei Tian ◽  
Jian-Nan Zhang ◽  
Zhi-Min Jin
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Functional Groups ◽  
High Probability ◽  
Internal Symmetry ◽  
Supramolecular Synthon ◽  
Π Interactions ◽  
Graph Set ◽  
Hydrogen Bonded

A fixed hydrogen-bonding motif with a high probability of occurring when appropriate functional groups are involved is described as a `supramolecular hydrogen-bonding synthon'. The identification of these synthons may enable the prediction of accurate crystal structures. The rare chiral hydrogen-bonding motifR53(10) was observed previously in a cocrystal of 2,4,6-trichlorophenol, 2,4-dichlorophenol and dicyclohexylamine. In the title solvated salt, 2C4H12N+·C6H3Cl2O−·(C6H3Cl2O−·C6H4Cl2O)·2C4H8O, five components, namely twotert-butylammonium cations, one 2,4-dichlorophenol molecule, one 2,4-dichlorophenolate anion and one 2,6-dichlorophenolate anion, are bound by N—H...O and O—H...O hydrogen bonds to form a hydrogen-bonded ring, with the graph-set motifR53(10), which is further associated with two pendant tetrahydrofuran molecules by N—H...O hydrogen bonds. The hydrogen-bonded ring has internal symmetry, with a twofold axis running through the centre of the 2,6-dichlorophenolate anion, and is isostructural with a previous and related structure formed from 2,4-dichlorophenol, dicyclohexylamine and 2,4,6-trichlorophenol. In the title crystal, helical columns are built by the alignment and twisting of the chiral hydrogen-bonded rings, along and across thecaxis, and successive pairs of rings are associated with each other through C—H...π interactions. Neighbouring helical columns are inversely related and, therefore, no chirality is sustained, in contrast to the previous case.

Sign in / Sign up

Export Citation Format

Share Document