Recognition of anions and monocarboxylic acids by a fluorescent guanidine-based receptor

Goswami, Shyamaprosad; Jana, Subrata; Chakrabarty, Rinku; Fun, Hoong‐Kun

doi:10.1080/10610270902980614

Cited by 6 publications

(3 citation statements)

References 9 publications

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“…After studying all the association constants with receptors 1-5, it is observed that the pyridyl imidazole host binds monocarboxylic acids with a higher efficiency compared to the previously reported pyridyl amide-based receptors. [8][9][10][11] Even the most simple phenyl imidazolebased receptor 5 shows association constants with monocarboxylic acid in the range of 10 6 -10 7 M -1 in both UV-Vis and fluorescence methods, although this type of receptor binds to the carboxyl moiety via a single-point hydrogen bonding interaction. The higher association constant of all these receptors may be attributed to the formation of a pseudo-bowl-shaped supramolecular cavity of both host molecules using a two-, three-, and fourpoint hydrogen bonding donor-acceptor array, which is reflected through the analysis of all titration results forming a 2:1 host-guest complex.…”

Section: Resultsmentioning

confidence: 99%

“…fluorescence switch and diguanidine-containing receptors for monocarboxylic acids have also been reported. [11] In continuation of our search for new motifs for the recognition of carboxylic acids, we report here the recognition behavior of imidazole-based receptors towards monocarboxylic acids. Notably, the imidazole moiety is an integral part of various natural products and drug molecules with a wide range of medicinal activities.…”

Section: Introductionmentioning

confidence: 97%

“…[ 8–10 ] Along with different designed receptors, anthracene‐containing pyridine amide‐based fluorescence switch and diguanidine‐containing receptors for monocarboxylic acids have also been reported. [ 11 ]…”

Section: Introductionmentioning

confidence: 99%

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Recognition of monocarboxylic acids by imidazole‐containing receptors

Prajapati

Shinha

Suryavanshi

et al. 2022

J of Physical Organic Chem

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The recognition of different monocarboxylic acids by a group of substituted imidazoles containing pyridyl moiety has been studied. This work highlights the substituent effects as well as the position of “nitrogen” in the attached pyridine moiety of the hosts during the recognition process. The strongest recognition ability is observed if the receptor contains the 2‐pyridyl moiety. The binding ability is weak for the imidazoles with a 3‐pyridyl unit, and it is close to the phenyl‐substituted imidazoles. The size of the monocarboxylic acids also plays a crucial role in the formation of the host–guest complexes. In all the cases, host and guest bind in 2:1 mode of complexation. This type of interaction is due to the angular supramolecular arrangement of two host molecules generating a cavity to bind the carboxylic acid through three‐ or four‐point hydrogen bonding. The phenyl substituents at the imidazole also slightly enhance the association of hosts and guests. The 1H NMR studies clearly demonstrate a host–guest interaction without any proton transfer in a neutral organic medium.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

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Recognition of monocarboxylic acids by imidazole‐containing receptors

Prajapati

Shinha

Suryavanshi

et al. 2022

J of Physical Organic Chem

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Supramolecular assembly of guanidinium benzilate and benzylammonium benzilate: structural and spectroscopic (FT-IR, UV–Vis and photoluminescence) analyses

Sankar,

Sudarsanan,

Chellathurai

et al. 2023

Chem. Pap.

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Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights

2016

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Recently we introduced iron trichloride as an environmentally benign and cost-efficient reagent for the synthesis of N-benzoylguanidines. This highly attractive synthetic approach grants access to a broad spectrum of N-benzoylguanidines under mild conditions in short reaction times. In this work we present an extended scope of our methodology along with the results obtained from mechanistic studies via in situ IR spectroscopy in combination with LC (liquid chromatography)-MS analyses. On the basis of these new mechanistic insights we were able to optimize the synthetic protocol and to develop an alternative mechanistic proposal. In this context the symbiotic roles of iron trichloride and oxygen in the guanylation process are highlighted.

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Recognition of anions and monocarboxylic acids by a fluorescent guanidine-based receptor

Cited by 6 publications

References 9 publications

Recognition of monocarboxylic acids by imidazole‐containing receptors

Recognition of monocarboxylic acids by imidazole‐containing receptors

Supramolecular assembly of guanidinium benzilate and benzylammonium benzilate: structural and spectroscopic (FT-IR, UV–Vis and photoluminescence) analyses

Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights

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