Synthesis and solid state self-assembly of an isatin–thiazoline hybrid driven by three self-complementary dimeric motifs

Ahmad, Munir; Pervez, Humayun; Hadda, Taïbi Ben; Toupet, Loı̈c; Naseer, Muhammad Moazzam

doi:10.1016/j.tetlet.2014.08.021

Cited by 22 publications

(10 citation statements)

References 59 publications

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“…These two features make this class of compounds more attractive than thioureas in crystal engineering. Very recently, we have highlighted these features using ferrocene-based thiosemicarbazones 53 and herein as a continuation of the previous work and our continuous research interests in the study of non-covalent interactions, [54][55][56][57] we report the synthesis of new structurally related coumarin-thiosemicarbazone hybrid molecules 3a-3c and using these molecules as a platform, demonstrate the robustness of the thioamide dimer {Á Á ÁH-N-CQS} 2 synthon of thiosemicarbazones. The purpose of introducing a freely rotatable coumarin moiety into these structures is to create a flexible environment for different possible non-covalent interactions.…”

Section: Introductionmentioning

confidence: 63%

Robustness of a thioamide {⋯H–N–CS}₂ synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarin–thiosemicarbazone hybrids

et al. 2015

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The applications of thioureas in crystal engineering have increased dramatically over the past few years. However, their analogs namely N-imino thioureas/thiosemicarbazones are largely ignored, despite the fact that these can be more interesting with respect to crystal engineering applications due to the presence of an additional N-imino moiety. Aiming to highlight their importance in crystal engineering/ supramolecular chemistry, three structurally related coumarin-thiosemicarbazone hybrids (3a-3c) have been designed, synthesized and crystallographically characterized. All of the compounds showed a general preference for the adoption of the cis, trans conformation around the central thiourea moiety; a conformation which is ideal for the formation of a dimeric hydrogen-bonded R 2 2 (8){Á Á ÁH-N-CQS} 2 synthon as the building block. Therefore, this dimeric synthon is observed in all of the compounds, regardless of the formation of layered to cage-like three dimensional supramolecular networks depending on different substituents. The prevalence of the cis, trans conformation and the robustness of the thioamide dimer synthon in thiosemicarbazones indicate its potential use as a design element in crystal engineering.

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Section: Introductionmentioning

confidence: 63%

Robustness of a thioamide {⋯H–N–CS}₂ synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarin–thiosemicarbazone hybrids

et al. 2015

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“…It is important to mention here that these are the same conditions for crystal growth as used previously for compound 1 [32]. applications in crystal engineering field [47].…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, isatin is structurally an ideal candidate to serve as a highly variable tecton for the construction of supramolecular assemblies due to its remarkable hydrogen bond donor/acceptor abilities and a relatively large molecular dipole moment [29][30][31]. Keeping this in view, we very recently reported the synthesis and solid state self-assembly of 5-fluoroisatin-based hybrid molecule 1, where no intermolecular interactions were observed for fluoro substituent in the presence of N-H···O, C-H···O, C-H···N, C-H···π, π···π, C-H···Cl interactions [32]. This observation and our continuous interest in supramolecular self-assemblies [33][34][35][36][37][38][39] increased our curiosity and prompted us to introduce 4-fluoro group as a substitute to 3-methoxy on the central N-aryl ring of the rigid core of isatin-thiazoline hybrid 1 to explore the existence of fluorine-mediated interactions in isatin-based compounds.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Pervez

Ahmad

Hadda

et al. 2015

Journal of Molecular Structure

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International audienceAn exciting isatin-thiazoline hybrid molecule 2 having -C=N-N=C- linkage has been synthesized in 88% yield by the reaction of 5-fluoroisatin with N-(4-fluorophenyl)hydrazinecarbothioamide followed by condensation of the resultant isatin-thiosemicarbazone intermediate with p-chlorophenacyl bromide. The solid state self-assembly of this hybrid molecule was studied by X-ray crystallographic technique. A layered assembly composed of 1D-chains with methanol molecules encapsulated between every two chains is obtained, making a bi-chain sandwich like structure. The supramolecular forces involved in the stabilization of this structure are importantly fluorine-mediated interactions (C-H···F, F···S and F···π) along with others i.e. N-H···O, O-H···O, C-H···O, Cl···π, C-H···π and π···π interactions. To the best of our knowledge, this is the first example of solid state fluorine-mediated C-H···F, F···S and F···π interactions found in a family of isatin-based compound

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“…As a continuation of our recent interests in supramolecular chemistry [24][25][26][27][28][29], herein we report a simple artificial colored receptor based on the well-known color dye isatin. The proposed receptor owns two different types of NH-hydrogen bond donors (NH-isatin and NH-thiourea-).…”

Section: Introductionmentioning

confidence: 96%

Isatin-3-thiosemicarbazone as Chromogenic Sensor for the Selective Detection of Fluoride Anion

Rasheed

Ahmed

Faisal

et al. 2020

Heterocyclic Communications

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In this study, we describe the anion recognition ability of isatin-3-thiosemicarbazone 2, which contains two different anion recognition units i.e. isatin NH and the thiourea moiety. Both have the ability to act as proton donors. Most importantly, a significant colour change of 2 was observed (from light yellow to reddish orange) in organic medium only after the addition of the F– anion. No such colour change could be observed for any other anions including Cl–, Br–, I–, ${{\text{H}}_{2}}\text{P}{{\text{O}}_{4}}^{-},$$\text{N}{{\text{O}}_{\text{2}}}^{-},$$\text{P}{{\text{F}}_{4}}^{-}$etc. The UV-Vis spectroscopic studies also indicate the potential of this compound for selective detection of fluoride anions. 1H-NMR titrations clearly indicate the formation of the 2.F– anionic complex. The Density-functional theory (DFT) calculations are also performed to get further insights on the formation of 2.F– complex.

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Synthesis and solid state self-assembly of an isatin–thiazoline hybrid driven by three self-complementary dimeric motifs

Cited by 22 publications

References 59 publications

Robustness of a thioamide {⋯H–N–CS}₂ synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarin–thiosemicarbazone hybrids

Robustness of a thioamide {⋯H–N–CS}₂ synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarin–thiosemicarbazone hybrids

Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Isatin-3-thiosemicarbazone as Chromogenic Sensor for the Selective Detection of Fluoride Anion

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Synthesis and solid state self-assembly of an isatin–thiazoline hybrid driven by three self-complementary dimeric motifs

Cited by 22 publications

References 59 publications

Robustness of a thioamide {⋯H–N–CS}2 synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarin–thiosemicarbazone hybrids

Robustness of a thioamide {⋯H–N–CS}2 synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarin–thiosemicarbazone hybrids

Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Isatin-3-thiosemicarbazone as Chromogenic Sensor for the Selective Detection of Fluoride Anion

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Robustness of a thioamide {⋯H–N–CS}₂ synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarin–thiosemicarbazone hybrids

Robustness of a thioamide {⋯H–N–CS}₂ synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarin–thiosemicarbazone hybrids