Adjustable Electrophilicity by Cooperative Hydrogen Bonds

Bauer, Mirko; Spange, Stefan

doi:10.1002/anie.201103585

Search citation statements

Order By: Relevance

Paper Sections

Select...

Substitution and Addition Reactions1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2012

2014

Publication Types

Select...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

(1 citation statement)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Simple electrophile-nucleophile combinations have been examined with the express aim of understanding whether hydrogen bonding can influence distant, yet electronically coupled reactive centres. 16 This process is extremely important in biological catalysis. Barbiturate merocyanines (Scheme 10) were utilised as model systems, as they possess both electrophilic character and a number of hydrogen-bonding sites.…”

Section: Substitution and Addition Reactionsmentioning

confidence: 99%

Reaction mechanisms: polar reactions

Yau

Croft

2012

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

View full text Add to dashboard Cite

Section: Substitution and Addition Reactionsmentioning

confidence: 99%

Reaction mechanisms: polar reactions

Yau

Croft

2012

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

View full text Add to dashboard Cite

Colorimetric detection of fluoride ion by 5-arylidenebarbituric acids: dual interaction mode for fluoride ion with single receptor

2014

View full text Add to dashboard Cite

Two 5-arylidenebarbituric acid derivatives (IH and IM) have been synthesized by the Knoevenagel condensation of barbituric acid with 4-N,N-dimethylamino benzaldehyde and studied for anion sensing activities. Both receptors sense fluoride ion with high selectivity and sensitivity and the sensing action has been demonstrated by naked eye detection, UV-visible absorption, and fluorescence spectral changes in the presence of F(-). Indeed, the F(-) sensing mechanism for receptor IH depends on F(-) ion concentration. While at higher concentrations F(-) forms strong hydrogen bonding interaction with the N-H proton of the receptor, at lower concentrations sensing is influenced by the deprotonation of the methylene proton, followed by the chemical reaction, which is also confirmed by the (1)H-NMR technique. On the other hand, when replacing the N-H proton with a methyl group, IM does not show any concentration dependent behaviour with F(-). The F(-) concentration dependent sensing is attributed to the changes in the receptor-anion interaction equilibrium, where at higher F(-) concentrations, F(-) interacts with the receptor through hydrogen bonding and at lower concentrations it induces a chemical reaction.

show abstract