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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

Functionalized Adenine-based Receptors for Monocarboxylic Acids’ Recognition

Author(s): Tanushree Sen*, Suman Adhikari, Nabajyoti Baildya and Kumaresh Ghosh*

Volume 28, Issue 16, 2024

Published on: 10 May, 2024

Page: [1288 - 1299] Pages: 12

DOI: 10.2174/0113852728303168240424052507

Price: $65

Abstract

Three receptors 1-3, built on adenine, have been synthesized, structurally characterized, and successfully employed for the recognition of monocarboxylic acids. The adenine- based receptors 1-3 have been found to bind monocarboxylic acids via the Hoogsteen (HG) binding site or the Watson-Crick (WC) binding site and form 1:1 complexes in CHCl3. Detailed binding of the receptors 1-3, in the presence of the monocarboxylic acids, corroborates that there is a distinct propensity of the HG site for aromatic carboxylic acids, for example, (S)-mandelic acid and benzoic acid. Aliphatic acids, for example, propanoic acid and rac-lactic acid, on the other hand, prefer to bind at the WC site. The monocarboxylic acid bindings to 1-3 were examined by UV–Vis, fluorescence, and 1H NMR spectroscopic methods, and DFT study.

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