Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-aminophenylarsonate tetrahydrate

Smith, Graham; Wermuth, Urs D.

doi:10.1107/s2056989016006691

Cited by 3 publications

(1 citation statement)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, the absence in the Crystallographic Data Base (CSD) [20] of any structures having the protonated form of the acid, the 4-arsonoanilinium cation [ [22]. We, therefore, began a trial investigation of the protontransfer salts of PARSH 2 with a series of strong organic *Corresponding author: Graham Smith, Science and Engineering Faculty, Queensland University of Technology, G.P.O.…”

Section: Introductionmentioning

confidence: 99%

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

Smith

Wermuth

2017

Zeitschrift Für Kristallographie - Crystalline Materials

Self Cite

View full text Add to dashboard Cite

The 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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

Smith

Wermuth

2017

Zeitschrift Für Kristallographie - Crystalline Materials

Self Cite

View full text Add to dashboard Cite

show abstract

Proton-transfer salts of diphenylphosphinic acid with substituted 2-aminopyridine: crystal structure, spectroscopic and DFT studies

Yuan

Zhang

et al. 2023

Acta Crystallogr C

View full text Add to dashboard Cite

Three proton-transfer salts of diphenylphosphinic acid (DPPA) with 2-amino-5-(X)-pyridine (AMPY, X = Cl, CN or CH3), namely, 2-amino-5-chloropyridinium diphenylphosphinate, C5H6ClN2 +·C12H10O2P− (1, X = Cl), 2-amino-5-cyanopyridinium diphenylphosphinate, C6H6N3 +·C12H10O2P− (2, X = CN), and 2-amino-5-methylpyridinium diphenylphosphinate, C6H9N2 +·C12H10O2P− (3, X = CH3), have been synthesized and characterized by FT–IR and 1H NMR spectroscopy, and X-ray crystallography. The crystal structures of compounds 1–3 were determined in the space group P\overline{1} for 1 and 2, and C2/c for 3. All three compounds contain N—H...O hydrogen-bonding interactions due to proton transfer from the O=P—OH group of DPPA as donor to the pyridine N atom of AMPY as acceptor. The proton transfer of compounds 1–3 was also verified by 1H NMR and FT–IR spectroscopy. The stoichiometry of all three proton-transfer salts was determined to be 1:1 and the Benesi–Hildebrand equation was applied to determine the formation constant (K CT) and the molar extinction coefficient (ɛCT) in each case. Theoretical density functional theory (DFT) calculations were performed to investigate the optimized geometries, the molecular electrostatic potentials (MEP) and the highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO) of all three proton-transfer salts. The results showed good agreement between the experimental data and the DFT computational analysis.

show abstract

Crystal structure of dibenzylammonium hydrogen (4-aminophenyl)arsonate monohydrate

Traoré,

Diallo,

Sidibé

et al. 2023

Acta Cryst E

View full text Add to dashboard Cite

The title salt, C14H16N+·C6H7AsNO3 −·H2O or [(C6H5CH2)2NH2][H2NC6H4As(OH)O2]·H2O, (I), was synthesized by mixing an aqueous solution of (4-aminophenyl)arsonic acid with an ethanolic solution of dibenzylamine at room temperature. Compound I crystallizes in the monoclinic P21/c space group. The three components forming I are linked via N—H...O and O—H...O intermolecular hydrogen bonds, resulting in the propagation of an infinite zigzag chain. Additional weak interactions between neighbouring chains, such as π–π and N—H...O contacts, involving phenyl rings, –NH2 and –As(OH)O3 functions, and H2O, respectively, lead to a three-dimensional network.

show abstract

Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-aminophenylarsonate tetrahydrate

Cited by 3 publications

References 41 publications

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

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

Proton-transfer salts of diphenylphosphinic acid with substituted 2-aminopyridine: crystal structure, spectroscopic and DFT studies

Crystal structure of dibenzylammonium hydrogen (4-aminophenyl)arsonate monohydrate

Contact Info

Product

Resources

About