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• W2326195090 endingPage "2341" @default.
• W2326195090 startingPage "2330" @default.
• W2326195090 abstract "Acetate anion plays an important role in several biochemical functions such as enzyme reaction, antibody response, and action of receptor molecules. This investigation reports the synthesis and molecular details of a unique receptor, 2-amino-N-(2-amino-benzyl)-benzamide (R) that senses selectively acetate via simultaneous involvement of one aromatic amine group and an amide proton of the receptor molecule. Solution-state NMR, steady-state fluorescence, and FT-IR examinations established that the acetate anion binds to the receptor with 1:1 ratio with high specificity. The binding was stabilized by two H-bond formations between the oxygen atoms of acetate anion and two H atoms, one from amide group and the other from the amine group of the receptor. The binding interaction caused significant changes in the chemical shift of the receptor protons, and the evaluated affinity constant, from the NMR measurements, was found to be 1.87 × 10(4) M(-1). Density functional theory (DFT) analysis further showed a significant rotation of one of the two aromatic rings leading to formation of a 10-member ring involving the acetate anion, amide proton, and the one amine group attached to aromatic ring. The H-bond patterns observed in the crystal structure were significantly changed due to complex formation. However, the changes in the geometrical arrangement in the complex caused a small but significant increase of the fluorescence emission. Acetate geometry and unique positioning of the amide and amine groups of the receptor render the recognition feasible, and DFT analysis estimated ∼30 kJ M(-1) stabilization due to 1:1 complexation. Such positioning and geometrical arrangement may make the receptor very specific to bind acetate anion, and as such R became a very relevant molecule in detection and function of the acetate anion present in complex biochemical systems." @default.
• W2326195090 created "2016-06-24" @default.
• W2326195090 creator A5017415148 @default.
• W2326195090 creator A5045279414 @default.
• W2326195090 creator A5078227113 @default.
• W2326195090 creator A5080505874 @default.
• W2326195090 date "2016-04-08" @default.
• W2326195090 modified "2023-10-16" @default.
• W2326195090 title "Molecular Details of Acetate Binding to a New Diamine Receptor by NMR and FT-IR Analyses" @default.
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• W2326195090 doi "https://doi.org/10.1021/acs.jpca.6b01078" @default.
• W2326195090 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/27029209" @default.
• W2326195090 hasPublicationYear "2016" @default.
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