Interaction Site and Proton Transfer Equilibrium in the 4-Aminoantipyrine-Pentachlorophenol Hydrogen–Bonded Adduct

Habeeb, Moustafa M.

doi:10.3184/030823402103172095

Cited by 3 publications

(2 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The result obtained in the PCP complexes is consistent with the inversion point of 35 Cl NQR frequencies [ 12 , 28 ]. In PCP–4MP, a proton transfer and isotope polymorphism have been reported [ 12 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. Since the large 1 H-NMR CS value of 18.6 ppm was recorded in TCP–IMID as compared with 17.8 ppm of PCP–4MP, it can be expected that the similar properties are obtained in TCP–IMID.…”

Section: Discussionmentioning

confidence: 99%

“…In a case of pentachlorophenol (abbreviated to PCP) complexes, it has been reported that PCP forms salts with nitrogen-bases (N-Base) covering a broad p K a range (0.65–11.20). These crystals have been employed to detect proton-transfer equilibrium between O–H···N (covalent form) and O − ···H–N + (ionic form) [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 ]. 35 Cl NQR frequency measurements have reported that the NQR frequencies give constant values of ca .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

1H-MAS-NMR Chemical Shifts in Hydrogen-Bonded Complexes of Chlorophenols (Pentachlorophenol, 2,4,6-Trichlorophenol, 2,6-Dichlorophenol, 3,5-Dichlorophenol, and p-Chlorophenol) and Amine, and H/D Isotope Effects on 1H-MAS-NMR Spectra

Honda

2013

Molecules

View full text Add to dashboard Cite

Chemical shifts (CS) of the 1H nucleus in N···H···O type hydrogen bonds (H-bond) were observed in some complexes between chlorophenols [pentachlorophenol (PCP), 2,4,6-tricholorophenol (TCP), 2,6-dichlorophenol (26DCP), 3,5-dichlorophenol (35DCP), and p-chlorophenol (pCP)] and nitrogen-base (N-Base) by solid-state high-resolution 1H-NMR with the magic-angle-spinning (MAS) method. Employing N-Bases with a wide range of pKa values (0.65–10.75), 1H-MAS-NMR CS values of bridging H atoms in H-bonds were obtained as a function of the N-Base’s pKa. The result showed that the CS values were increased with increasing pKa values in a range of ΔpKa < 0 [ΔpKa = pKa(N-Base) - pKa(chlorophenols)] and decreased when ΔpKa > 2: The maximum CS values was recorded in the PCP (pKa = 5.26)–4-methylpyridine (6.03), TCP (6.59)–imidazole (6.99), 26DCP (7.02)–2-amino-4-methylpyridine (7.38), 35DCP (8.04)–4-dimethylaminopyridine (9.61), and pCP (9.47)–4-dimethylaminopyridine (9.61) complexes. The largest CS value of 18.6 ppm was recorded in TCP–imidazole crystals. In addition, H/D isotope effects on 1H-MAS-NMR spectra were observed in PCP–2-amino-3-methylpyridine. Based on the results of CS simulation using a B3LYP/6-311+G** function, it can be explained that a little changes of the N–H length in H-bond contribute to the H/D isotope shift of the 1H-MAS-NMR peaks.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

1H-MAS-NMR Chemical Shifts in Hydrogen-Bonded Complexes of Chlorophenols (Pentachlorophenol, 2,4,6-Trichlorophenol, 2,6-Dichlorophenol, 3,5-Dichlorophenol, and p-Chlorophenol) and Amine, and H/D Isotope Effects on 1H-MAS-NMR Spectra

Honda

2013

Molecules

View full text Add to dashboard Cite

show abstract

A facile synthesis of thiosemicarbazides containing the 4-antipyrinyl group under microwave irradiation in solvent-free conditions

Zheng

Liu

et al. 2006

Journal of Sulfur Chemistry

View full text Add to dashboard Cite

show abstract

Fabrication and characterization of 4-aminoantipyrine electrospun nanofiber polymer membranes for rapid visualization of pentachlorophenol in water samples

et al. 2022

View full text Add to dashboard Cite

In this work, we pioneered the development of a novel 4-aminoantipyrine loaded polylactic acid electrospun membrane for visualization and rapid detection of pentachlorophenol in water samples. The morphology, pH value, selectivity and detection sensitivity of electrospun membranes were systematically studied and optimized. The study found that the detection limit of the electrospun nanofiber polylactic acid membrane loaded with 4-aminoantipyrine was 0.4 mg/L, and the effective detection time was 0.5 h. The membranes have good stability after one month of storage in the dark at room temperature, the selectivity of 4-aminoantipyrineloaded polylactic acid electrospun membranes to other and its analogs in aqueous environment was then compared. The actual sample (including drinking water, tap water used in our lives, lake water and temporary water samples collected during production, transportation and distribution of fish) test result is negative. The fast-response electrospun nanofiber polylactic acid membrane loaded with 4-aminoantipyrine have available detection limits, simple detection methods, fast detection times, no secondary contamination of the solution to be tested, and the amount of sample required extremely small, showed great potential for materials science, environmental monitoring and food safety inspection.

show abstract

Interaction Site and Proton Transfer Equilibrium in the 4-Aminoantipyrine-Pentachlorophenol Hydrogen–Bonded Adduct

Abstract: The hydrogen-bonding interaction site between 4-aminoantipyrine (4AAP) and pentachlorophenol (PCP) was investigated in the crystalline form using FT-IR and in solution using FT-IR, UV-Vis and 1H,13C NMR spectroscopies.

Cited by 3 publications

References 11 publications

1H-MAS-NMR Chemical Shifts in Hydrogen-Bonded Complexes of Chlorophenols (Pentachlorophenol, 2,4,6-Trichlorophenol, 2,6-Dichlorophenol, 3,5-Dichlorophenol, and p-Chlorophenol) and Amine, and H/D Isotope Effects on 1H-MAS-NMR Spectra

1H-MAS-NMR Chemical Shifts in Hydrogen-Bonded Complexes of Chlorophenols (Pentachlorophenol, 2,4,6-Trichlorophenol, 2,6-Dichlorophenol, 3,5-Dichlorophenol, and p-Chlorophenol) and Amine, and H/D Isotope Effects on 1H-MAS-NMR Spectra

A facile synthesis of thiosemicarbazides containing the 4-antipyrinyl group under microwave irradiation in solvent-free conditions

Fabrication and characterization of 4-aminoantipyrine electrospun nanofiber polymer membranes for rapid visualization of pentachlorophenol in water samples

Contact Info

Product

Resources

About