A dihydrogen phosphate selective anion receptor based on acylhydrazone and pyrazole

Pandian, Thiravidamani Senthil; Choi, Yusun; Srinivasadesikan, Venkatesan; Lin, Ming‐Chang; Kang, Jongmin

doi:10.1039/c4nj01063a

Cited by 17 publications

(6 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among the three anions (HP 2 O 7 3− , CH 3 COO − , H 2 PO 4 − ) the HP 2 O 7 3− anion shows the highest binding energy with larger number of hydrogen bonds. The N─H…O type hydrogen bonding has observed to be stronger than the C─H…O type hydrogen bonding for all the anions studied here which is close agreement with the previous report . The calculated binding energies in solvent phase are in good agreement with the experimentally calculated UV binding energies, qualitatively and quantitatively.…”

Section: Resultssupporting

confidence: 91%

“…The N─H…O type hydrogen bonding has observed to be stronger than the C─H…O type hydrogen bonding for all the anions studied here which is close agreement with the previous report. 13 The calculated binding energies in solvent phase are in good agreement with the experimentally calculated UV Figure 9. Most stable structure for Host…HP 2 O 7 3− complex in solvent phase (DMSO) optimized with B3LYP/6-31 g (d) using Gaussian 09.…”

Section: Bulletin Of the Korean Chemical Societysupporting

confidence: 79%

See 1 more Smart Citation

A Hydrogen Pyrophosphate Selective Anion Receptor Based on Thiosemicarbazone

Pandian¹,

Srinivasadesikan

Lin

et al. 2017

Bulletin Korean Chem Soc

Self Cite

View full text Add to dashboard Cite

A novel rigid anion receptor 1 containing thiosemicarbazone groups were synthesized. Receptor 1 displayed competitive turn‐off fluorescence and colorimetric response for hydrogen pyrophosphate. This recognition process was confirmed by UV–vis, fluorescence titrations. A detailed analysis of the TD‐density functional theory calculations was consistent with the observed colorimetric experiments. These experiments revealed that the colorimetric and fluorescent response is triggered by thiourea/ HP2O73− hydrogen bonding.

show abstract

Section: Resultssupporting

confidence: 91%

Section: Bulletin Of the Korean Chemical Societysupporting

confidence: 79%

A Hydrogen Pyrophosphate Selective Anion Receptor Based on Thiosemicarbazone

Pandian¹,

Srinivasadesikan

Lin

et al. 2017

Bulletin Korean Chem Soc

Self Cite

View full text Add to dashboard Cite

show abstract

“…Recently, Kang and co-workers reported the densely functionalized nitrogen-rich anion receptor 259 (Figure 194), with a photoactive anthracene group as the central spacer and two arms with acylhydrazone and pyrazole binding sites endcapped by a p-nitrophenyl group as a chromogenic unit. 183 Receptor 259 formed a stable 1:1 complex with a H Theoretically, the calculated structure of the host−guest complex revealed that all the N−H protons acted as donors for the H 2 PO 4 − anion. Overall, four types of N−H•••O hydrogen bonding were observed in the host−guest complex.…”

Section: Chemical Reviewsmentioning

confidence: 96%

“…Recently, Kang and co-workers reported the densely functionalized nitrogen-rich anion receptor 259 (Figure ), with a photoactive anthracene group as the central spacer and two arms with acylhydrazone and pyrazole binding sites end-capped by a p -nitrophenyl group as a chromogenic unit …”

Section: Use Of More Than Two Noncovalent Interactionsmentioning

confidence: 99%

See 1 more Smart Citation

Anion Recognition Strategies Based on Combined Noncovalent Interactions

2017

View full text Add to dashboard Cite

This review highlights the most significant examples of an emerging field in the design of highly selective anion receptors. To date, there has been remarkable progress in the binding and sensing of anions. This has been driven in part by the discovery of ways to construct effective anion binding receptors using the dominant N-H functional groups and neutral and cationic C-H hydrogen bond donors, as well as underexplored strong directional noncovalent interactions such as halogen-bonding and anion-π interactions. In this review, we will describe a new and promising strategy for constructing anion binding receptors with distinct advantages arising from their elaborate design, incorporating multiple binding sites able to interact cooperatively with anions through these different kinds of noncovalent interactions. Comparisons with control species or solely hydrogen-bonding analogues reveal unique characteristics in terms of strength, selectivity, and interaction geometry, representing important advances in the rising field of supramolecular chemistry.

show abstract

End Group Effects on Anion Binding in Tetraglycine Peptide: A Computational Study

Sarma,

Sarmah,

Sarma

2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

The importance of anions in various processes has led to a search for molecules that can effectively recognize and interact with these anions. This study explores how the tetraglycine (Gly)4 peptide in its zwitterionic, neutral, and terminally capped forms acts as a receptor for H2PO4− and HSO4− anions within the framework of supramolecular host‐guest chemistry. Using molecular dynamics (MD) simulations, we obtained the conformations of the receptor‐anion complexes. Density functional theory (DFT), quantifies the complexes’ interaction energies in both gas and solvent phases. Proton transfer within the zwitterionic complex with H2PO4− anion alters peptide charge distribution, affecting its conformation and binding site arrangement, as analysed by quantum mechanics/molecular mechanics (QM/MM) methods. Symmetry‐adapted perturbation theory (SAPT) and noncovalent interactions analysis highlight the role of electrostatic interactions in these receptor‐anion complexes. It emphasizes the key interactions such as N‐H···O and O‐H···O=C between the peptide backbone and anions and elucidates the molecular recognition mechanism driven by crucial noncovalent interactions. The termination of the peptide’s end groups modulates anion binding sites from the backbone to the charged N‐terminal, resulting in distinct binding sites. Our findings provide insights for designing peptides tailored to function as anion receptors in diverse supramolecular chemistry applications.

show abstract

A dihydrogen phosphate selective anion receptor based on acylhydrazone and pyrazole

Abstract: A novel chromogenic anion receptor 1 based on acylhydrazone and pyrazole has been designed and synthesized. Receptor 1 forms stable 1 : 1 complexes with dihydrogen phosphate and other halide anions in DMSO solution.

Cited by 17 publications

References 27 publications

A Hydrogen Pyrophosphate Selective Anion Receptor Based on Thiosemicarbazone

A Hydrogen Pyrophosphate Selective Anion Receptor Based on Thiosemicarbazone

Anion Recognition Strategies Based on Combined Noncovalent Interactions

End Group Effects on Anion Binding in Tetraglycine Peptide: A Computational Study

Contact Info

Product

Resources

About