NMR study of the coordinating behavior of 2,6-bis(benzimidazol-2?-yl)pyridine

Ceniceros‐Gómez, Agueda E.; Ramos-Organillo, Ángel; Hernández-Díaz, Julio; Nieto‐Martínez, Jonathan; Contreras, Rosalinda; Castillo‐Blum, Silvia E.

doi:10.1002/1098-1071(2000)11:6<392::aid-hc6>3.0.co;2-g

Cited by 23 publications

(3 citation statements)

References 24 publications

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“…2); no relation was observed between temperature and the speed of the tautomeric equilibrium, as observed by other authors for similar compounds. 37,38 The presence of one tautomer was observed in spectra in solvent acetone-d 6 and low concentration MeOD and CDCl 3 samples (Fig. 2).…”

Section: Resultsmentioning

confidence: 89%

New azaheterocyclic aromatic diphosphonates for hybrid materials for fuel cell applications

2013

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Section: Resultsmentioning

confidence: 89%

New azaheterocyclic aromatic diphosphonates for hybrid materials for fuel cell applications

2013

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“…From the reported 13 C data for BI 3 , as well as their protonated and deprotonated derivatives, in DMSOd 6 as solvent, Table 3 [ 30 ], the tautomeric proportion can be calculated. For BI, the δ obs value is 116.3, then the estimation is 63% of the pyridine character (+N3H).…”

Section: Estimation Of the Anular Tautomerism On Benzimidazolmentioning

confidence: 99%

13C-NMR Chemical Shifts in 1,3-Benzazoles as a Tautomeric Ratio Criterion

et al. 2022

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Benzimidazole is an important heterocyclic fragment, present in many biologically active compounds with a great variety of therapeutic purposes. Most of the benzimidazole activities are explained through the existence of 1,3-tautomeric equilibrium. As the binding affinity of each tautomer to a protein target depends on an established bioactive conformation, the effect of tautomers on the ligand protein binding mechanism is determinant. In this work, we searched and analyzed a series of reported 13C-NMR spectra of benzazoles and benzazolidine-2-thiones with the purpose of estimating their tautomeric equilibrium. Herein, several approaches to determine this problem are presented, which makes it a good initial introduction to the non-expert reader. This chemical shift difference and C4/C7 signals of benzimidazolidine-2-thione and 1-methyl-2-thiomethylbenzimidazole as references were used in this work to quantitatively calculate, in solution, the pyrrole–pyridine tautomeric ratio in equilibrium. The analysis will help researchers to correctly assign the chemical shifts of benzimidazoles and to calculate their intracyclic or exocyclic tautomeric ratio as well as mesomeric proportion in benzimidazoles.

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“…The I 0 /I 1 versus [Fe 3+ ] is a straight line, indicating that there is only a single quenching mechanism in this system. Investigating the fluorescence sensor based on benzimidazole, it is found that the quenching mechanism is generally forming a complex between the sp 2 nitrogen atom and the metal ions (42). Therefore, the mechanism of fluorescence quenching of (+)-PPBIPV towards Fe 3+ is static quenching in water.…”

Section: Sensing Properties Of (+)-Ppbipvmentioning

confidence: 99%

Novel benzimidazole-based conjugated polyelectrolytes: synthesis, solution photophysics and fluorescent sensing of metal ions

Wei

et al. 2020

E-Polymers

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AbstractTwo benzimidazole-based conjugated polyelectrolytes (+)-PPBIPV and (-)-PPBIPV which have opposite charges on their side chains were synthesized via Heck coupling reaction and characterized by 1H-NMR, UV-vis and PL spectroscopy. These two polyelectrolytes are both consisted of benzimidazole derivatives and phenylenevinylene units. The absorption and emission spectra reveal that the polymers both have solvent-dependency and concentration-dependency, and they exhibit aggregation effect in aqueous solution. In the respect of ion detection, the aqueous solution of (+)-PPBIPV has excellent selectivity and sensitivity for Fe3+. Moreover, Pd2+ can almost completely quench the fluorescence of (+)-PPBIPV in methanol solution, and its quenching constant KSV is 5.93×104 M-1. For (-)-PPBIPV, Sn2+ can double the fluorescence intensity of its aqueous solution, while (-)-PPBIPV has good identification for Fe3+ in methanol with a KSV = 3.44×105 M-1. Hence, two polyelectrolytes have considerable potential to become effective fluorescent sensing materials for some specific metal ions. All of the stoichiometric relationships between metal ions and conjugated polyelectrolytes were calculated using Benesi-Hildebrand equation.

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NMR study of the coordinating behavior of 2,6-bis(benzimidazol-2?-yl)pyridine

Cited by 23 publications

References 24 publications

New azaheterocyclic aromatic diphosphonates for hybrid materials for fuel cell applications

New azaheterocyclic aromatic diphosphonates for hybrid materials for fuel cell applications

13C-NMR Chemical Shifts in 1,3-Benzazoles as a Tautomeric Ratio Criterion

Novel benzimidazole-based conjugated polyelectrolytes: synthesis, solution photophysics and fluorescent sensing of metal ions

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