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

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.

Structure-Making with 3,5-Dimitrosalicylic Acid. I. The Proton Transfer Compounds of 3,5-Dinitrosalicylic Acid with a Series of Aliphatic Amines

2002 ◽  
Vol 55 (5) ◽  
pp. 349 ◽  
Author(s):  
G. Smith ◽  
U. D. Wermuth ◽  
P. C. Healy ◽  
R. C. Bott ◽  
J. M. White
Keyword(s):  
Hydrogen Bonding ◽  
Proton Transfer ◽  
Lewis Base ◽  
Aliphatic Amines ◽  
Tertiary Amines ◽  
Carboxylate Oxygen ◽  
Phenolic Oxygen ◽  
Phenolic Group ◽  
Intramolecular Hydrogen ◽  
Proton Transfer Compounds

The crystal structures of the proton-transfer compounds of 3,5-dinitrosalicylic acid (dnsa) with ammonia (two polymorphs) and a series of common aliphatic amines (methylamine, triethylamine, hexamethylenetetramine and ethylenediamine) have been determined and the hydrogen-bonding associations in each analysed. The compounds are [(NH4)+(dnsa)-] (1A, 1B), [(CH3NH3)+(dnsa)-] (2), [{(C2H5)3NH}+(dnsa)-] (3), [(C6H12 N4H)+(dnsa)-] (4) and [{(CH2 NH3) 2}2+(dnsa)2-�H2O] (5). It is of interest that with hydrate (5) the phenolic proton of dnsa is also lost on reaction, giving a rare dianionic species. In all compounds, protonation of the amino group of the Lewis base occurs, with subsequent hydrogen bonding via this and other hydrogens variously to the carboxylic, nitro and phenolic oxygens of dnsa, and in the case of (5), the lattice water. The result is the formation of simple linear associations with the tertiary amines, or network polymers with the less-substituted examples. Short intramolecular hydrogen bonds between the phenolic group and the carboxylate group are found in all compounds except (5), with the proton localized on the carboxylate oxygen rather than on the phenolic oxygen, but in the case of (3), delocalized within the hydrogen bond.

scholarly journals Proton-transfer compounds featuring the unusual 4-arsonoanilinium cation from the reaction of (4-aminophenyl)arsonic acid with strong organic acids

2018 ◽  
Vol 233 (2) ◽  
pp. 145-151
Author(s):  
Graham Smith ◽  
Urs D. Wermuth
Keyword(s):  
Hydrogen Bonding ◽  
Proton Transfer ◽  
Organic Acids ◽  
Picric Acid ◽  
Three Dimensional ◽  
Water Molecules ◽  
Fold Axis ◽  
Arsanilic Acid ◽  
Arsonic Acid ◽  
Proton Transfer Compounds

AbstractThe crystal structures of the 1:1 proton-transfer compounds of (4-aminophenyl)arsonic acid (p-arsanilic acid) with the strong organic acids, 2,4,6-trinitrophenol (picric acid), 3,5-dinitrosalicylic acid, (3-carboxy-4-hydroxy)benzenesulfonic acid (5-sulfosalicylic acid) and toluene-4-sulfonic acid have been determined at 200 K and their hydrogen–bonding patterns examined. The compounds are, respectively, anhydrous 4-arsonoanilinium 2,4,6-trinitrophenolate (1), the hydrate 4-arsonoanilinium 2-carboxy-4,6-dinitrophenolate monohydrate (2), the hydrate 4-arsonoanilinium (3-carboxy-4-hydroxy)benzenesulfonate monohydrate (3) and the partial solvate 4-arsonoanilinium toluene-4-sulfonate 0.8 hydrate (4). The asymmetric unit of2, a phenolate, comprises two independent but conformationally similar cation-anion pairs and two water molecules of solvation, and in all compounds, extensive inter-species hydrogen–bonding interactions involving arsono O–H···O and anilinium N–H···O hydrogen–bonds generate three-dimensional supramolecular structures. In the cases of1and2, the acceptors include phenolate and nitro O-atom acceptors, with3and4, additionally, sulfonate O-atom acceptors, and with the hydrates2–4, the water molecules of solvation. A feature of the hydrogen–bonding in3is the presence of primary chains extending along (010) through centrosymmetric cyclicR22(8) motifs together with conjoined cyclicR34(12) motifs, which include the water molecule of solvation. The primary hydrogen–bonding in the substructure of4involves homomolecular cation–cation arsono O–H···O interactions forming columns down the crystallographic four-fold axis of the unit cell.

scholarly journals Multifunctional Chiral Three-Dimensional Phosphite Frameworks Showing Dielectric Anomaly and High Proton Conductivity

2021 ◽  
Vol 9 ◽  
Author(s):  
S. S. Yu ◽  
C. Y. Xu ◽  
X. Pan ◽  
X. Q. Pan ◽  
H. B. Duan ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Proton Transfer ◽  
Proton Conductivity ◽  
Dielectric Response ◽  
Room Temperature ◽  
Three Dimensional ◽  
Dielectric Anomaly ◽  
High Proton Conductivity ◽  
High Proton ◽  
Hydrogen Bonding Networks

Chair 3D Co(II) phosphite frameworks have been prepared by the ionothermal method. It belongs to chiral space group P3221, and the whole framework can be topologically represented as a chiral 4-connected qtz net. It shows a multistep dielectric response arising from the reorientation of Me2-DABCO in the chiral cavities. It can also serve as a pron conductor with high conductivity, 1.71 × 10−3 S cm−1, at room temperature, which is attributed to the formation of denser hydrogen-bonding networks providing efficient proton-transfer pathways.

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