Study of picrate salts with amines

Goel, Nidhi; Singh, Gurdip; Srivastava, Pratibha

doi:10.1016/j.molstruc.2012.12.020

Cited by 26 publications

(6 citation statements)

References 27 publications

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“…Despite the widespread occurrence of amide functionalities throughout organic chemistry, few structures of other pharmaceutically relevant amide salts are known. Most crystallographic examples of protonated amides are simple uronium or methyl uronium ions, though structures of more complicated species are known, as is the structure of an HCl salt of the API, dutasteride …”

Section: Introductionmentioning

confidence: 99%

Salt Forms of Amides: Protonation and Polymorphism of Carbamazepine and Cytenamide

Buist

Kennedy

Shankland

et al. 2013

Crystal Growth & Design

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In situ generation of HCl or HBr in alcohol leads to O-protonation of the amide group of carbamazepine. Six salt phases have been produced using this method and their crystal structures determined by single crystal diffraction. A new polymorph of carbamazepine hydrochloride is described as are two polymorphs of carbamazepine hydrobromide. All are protonated at the amide O atom to give RC(OH)NH 2 cations. Prolonged exposure to air results in addition of water to the solid salt forms. Such hydration of carbamazepine hydrobromide simply gives a monohydrated phase, but similar treatment of the equivalent hydrochloride results in partial loss of HCl and the transfer of the remaining proton from the amide group to water to give [carbamazepine][H 3 O] 0.5 [Cl] 0.5 •H 2 O. A similar hydronium chloride species is the only product isolated after reaction of the carbamazepine analogue cytenamide with HCl generated in methanol.

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Section: Introductionmentioning

confidence: 99%

Salt Forms of Amides: Protonation and Polymorphism of Carbamazepine and Cytenamide

Buist

Kennedy

Shankland

et al. 2013

Crystal Growth & Design

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“…Normally, the NH stretching vibration is observed at around 3500 − 3400 cm − 1 . However, for solids 1 and 2 it occurs a red shift due to hydrogen intermolecular interactions between donor and acceptor, contributing to the increase in the bond length -NH, shifting it to lower frequencies vibrations [19]. The νC-O stretching of picrate ion was assigned to the bands in the region 1261 cm − 1 for 1 and 1269 cm − 1 for 2.…”

Section: Characterization Of Compounds 1 Andmentioning

confidence: 96%

Picrate salts with bipyridine derivatives: intramolecular and intermolecular aspects

2023

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Here, we present the preparation and characterization of two novel picrate salts. Compound 1 (DPK-PA) crystallizes in the triclinic system and centrosymmetric space group P , with unit cell parameters a = 9.378(17) Å, b = 9.790(15) Å, c = 10.141(16) Å, α = 99.63(7)°, β = 99.09(8)° and γ = 102.55(8)°, while the compound 2 (BBBPY-PA) crystallizes in the non-centrosymmetric P2 1 2 1 2 1 space group, orthorhombic unit cell parameters a = 6.3902(6) Å, b = 23.416(3) Å and c = 16.7320(18) Å. Both crystal structures present an ion-pair in the asymmetric unit, one picrate anion, and one bipyridine derivative. In the compound 1 structure, the molecule of DPK presents one intramolecular N1-H…N Hbond that contributes to stabilizing the planar conformation of DPK. The absence of intramolecular Hbonding in compound 2 can be explained by the steric hindrance of the tert-butyl group. For 1 and 2, the crystal packing is stabilized N-H…O strong hydrogen bonding interactions, which could be identi ed by the Hirsh eld Surface analysis and ngerprint plots. The compounds were also studied by UV-Vis and infrared analyses, which may support the statement of the formation of new material. Finally, as an attempt to obtain a molecular system to act as a chemical sensor, we studied the uorescence of both compounds, in solution and in solid state, however, no uorescence was observed.

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“…A proton transfer mechanism may be a key step in thermal decomposition, which is an intriguing aspect of the study of energetic picrates explosive properties. [23] Picrates are interesting because of their low cost, ultrafast reaction, hydrogen bonding, aromaticaromatic interactions, and other properties. It is an undeniable fact that when a picryl group is added into an organic compound, density rises.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic (UV and fluorescence), biological, DFT and molecular docking studies of 3,5‐diethyl‐2r,6c‐di(4‐fluorophenyl)piperidin‐4‐one picrate

Savithiri,

Bharanidharan

2021

Vietnam Journal of Chemistry

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The spectroscopic investigations of 3,5‐diethyl‐2r,6c‐di(4‐fluorophenyl)piperidin‐4‐one picrate (3,5‐DEDFPP) are evaluated by UV–Vis and fluorescence techniques. At the B3LYP/6‐311++G(d,p) level of theory, the DFT approach was utilized to optimize the molecular structure. The dipole moment, polarizability, and hyperpolarizability values are calculated at same level of theory. NBO analysis was used to calculate the hyperconjugative interaction energy (E(2)) and electron densities of donor (i) and acceptor (j) bonds. The molecule's energy gap was discovered using HOMO and LUMO calculation. The Mulliken atomic charges of the carbon, nitrogen and oxygen atoms were calculated and using at the same level. The thermodynamic properties of the title compound were calculated at different temperatures in gas phase. The 3,5‐DEDFPP's bacterial activity was evaluated against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Vibreo cholerae, and Pseudomonas aeruginosa, as well as fungal strains such as Candida albicans, Aspergillus niger, Aspergillus flavus, and Trichophyton rubrum. The interaction of the title compound to bind to a target protein was studied using molecular docking analysis.

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Study of picrate salts with amines

Cited by 26 publications

References 27 publications

Salt Forms of Amides: Protonation and Polymorphism of Carbamazepine and Cytenamide

Salt Forms of Amides: Protonation and Polymorphism of Carbamazepine and Cytenamide

Picrate salts with bipyridine derivatives: intramolecular and intermolecular aspects

Spectroscopic (UV and fluorescence), biological, DFT and molecular docking studies of 3,5‐diethyl‐2r,6c‐di(4‐fluorophenyl)piperidin‐4‐one picrate

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