Molbank

7 pages, 1118 KiB

Open AccessShort Note

4-([1,1′:3′,1′′-terphenyl]-2′-yloxy)-5-chlorophthalonitrile

by Dmitry Erzunov, Vyacheslav Baklagin, Igor Abramov, Vladimir Maizlish, Roman Rumyantsev and Arthur Vashurin

Molbank 2025, 2025(3), M2028; https://doi.org/10.3390/M2028 - 24 Jun 2025

Abstract

The study focuses on the synthesis and detailed crystal structure analysis of 4-([1,1′:3′,1′′-terphenyl]-2′-yloxy)-5-chlorophthalonitrile. Using X-ray diffraction methods, the authors achieved the precise refinement of the atomic arrangement, revealing the specific spatial organization of molecules within the crystal lattice. The manuscript thoroughly discusses the [...] Read more.

The study focuses on the synthesis and detailed crystal structure analysis of 4-([1,1′:3′,1′′-terphenyl]-2′-yloxy)-5-chlorophthalonitrile. Using X-ray diffraction methods, the authors achieved the precise refinement of the atomic arrangement, revealing the specific spatial organization of molecules within the crystal lattice. The manuscript thoroughly discusses the key intermolecular interactions—such as hydrogen bonding and π-π stacking—that govern the crystal packing. These interactions play a crucial role in stabilizing the structure and have a direct impact on the material’s physical and chemical properties, including its thermal stability and optical characteristics. Full article

(This article belongs to the Section Structure Determination)

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9 pages, 4166 KiB

Open AccessCommunication

The Absolute Configuration Determination of Patagonic Acid

by Eva E. Soto-Guzmán, Hilda J. Pagaza-Ibarra, Antonio J. Oliveros-Ortiz, Gabriela Rodríguez-García, Yliana López, Brenda Y. Bedolla-García, Carlos M. Cerda-García-Rojas, Christine Thomassigny, Mario A. Gómez-Hurtado, Armando Talavera-Alemán and Rosa E. del Río

Molbank 2025, 2025(3), M2027; https://doi.org/10.3390/M2027 - 23 Jun 2025

Abstract

(−)-Patagonic acid (1) is a clerodane diterpene isolated from several plants from the Alismataceae, Asteraceae, Euphorbiaceae, Fabaceae, Lamiaceae, Salicaceae, Sapindaceae, and Velloziaceae families, and its biological potential as an inhibitor of butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) and as an anti-inflammatory compound [...] Read more.

(−)-Patagonic acid (1) is a clerodane diterpene isolated from several plants from the Alismataceae, Asteraceae, Euphorbiaceae, Fabaceae, Lamiaceae, Salicaceae, Sapindaceae, and Velloziaceae families, and its biological potential as an inhibitor of butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) and as an anti-inflammatory compound has been described. Furthermore, the enantiomer (+)-1 is also described in Fabaceae and Verbenaceae. A lack of formal studies about the absolute configuration (AC) determination of 1 is emphasized. Thus, the present manuscript describes the AC determination of patagonic acid (1). The chemical correlation of (−)-1 from (−)-hardwickiic acid (2) was achieved by a simplistic oxidative process. The specific rotation value and electronic circular dichroism (ECD) analysis allowed for the AC determination of (−)-1 as (5R,8R,9S,10R)-(−)-patagonic acid. ECD revealed a positive exciton chirality (EC) phenomenon in both (−)-1 and (−)-2, which is directly associated with their configuration and conformational preferences, which were assessed by DFT calculations at the B3LYP/DGDZVP level of theory. Since the NMR data of (+)-1 are fully coincident with those from its enantiomer studied herein, the chirality of (5S,8S,9R,10S)-(+)-patagonic acid could also be determined. These experimental conclusions deeply complement the literature related to clerodane compounds biosynthesized in several families of plants of scientific interest. Full article

(This article belongs to the Section Natural Product Chemistry)

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Graphical abstract

6 pages, 1320 KiB

Open AccessShort Note

N-(2-((2-(1H-indol-3-yl)ethyl)carbamoyl)phenyl)furan-2-carboxamide

by Diyana Dimitrova, Iliyan Ivanov, Stanimir Manolov and Dimitar Bojilov

Molbank 2025, 2025(3), M2025; https://doi.org/10.3390/M2025 - 20 Jun 2025

Abstract

In the present study, we describe the synthesis of N-(2-((2-(1H-indol-3-yl)ethyl)carbamoyl)phenyl)furan-2-carboxamide via a two-step reaction sequence. Initially, isatoic anhydride was reacted with tryptamine to afford the corresponding intermediate, which was subsequently subjected to acylation using furan-2-carbonyl chloride. The final product was [...] Read more.

In the present study, we describe the synthesis of N-(2-((2-(1H-indol-3-yl)ethyl)carbamoyl)phenyl)furan-2-carboxamide via a two-step reaction sequence. Initially, isatoic anhydride was reacted with tryptamine to afford the corresponding intermediate, which was subsequently subjected to acylation using furan-2-carbonyl chloride. The final product was comprehensively characterized by melting point analysis, ¹H and ¹³C NMR, HSQC, IR, and MS spectrometry. The combined spectroscopic and analytical data unequivocally confirm the successful synthesis and structural integrity of the target compound. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 335 KiB

Open AccessShort Note

2-(2-(Benzylamino)-2-Oxoethyl)-1-Methyl-1H-Pyrrole-3-Carboxylic Acid

by Monika Fryc, Beata Gryzło, Pravin Kumar and Agnieszka Zagórska

Molbank 2025, 2025(3), M2026; https://doi.org/10.3390/M2026 (registering DOI) - 20 Jun 2025

Abstract

Here, 2-(2-(Benzylamino)-2-oxoethyl)-1-methyl-1H-pyrrole-3-carboxylic acid was efficiently synthesised in good yield via an amide coupling reaction between 2-carboxymethyl-1-methyl-1H-pyrrole-3-carboxylic acid and benzylamine, employing TBTU as the coupling reagent and DIPEA as the base. The reaction was carried out in dichloromethane at room [...] Read more.

Here, 2-(2-(Benzylamino)-2-oxoethyl)-1-methyl-1H-pyrrole-3-carboxylic acid was efficiently synthesised in good yield via an amide coupling reaction between 2-carboxymethyl-1-methyl-1H-pyrrole-3-carboxylic acid and benzylamine, employing TBTU as the coupling reagent and DIPEA as the base. The reaction was carried out in dichloromethane at room temperature. The compound was characterised by melting point determination, ¹H and ¹³C NMR, IR spectroscopy, and mass spectrometry. The combined analytical data confirm the target molecule’s successful synthesis and structural integrity. Full article

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8 pages, 882 KiB

Open AccessShort Note

bis(2-Phenylpyridinato)-[4,4′-bis(iodoethynyl)-2,2′-bipyridine]-iridium(III) Hexafluorophosphate

by Patrick Endres, Nishi Singh, Andreas Winter, Helmar Görls and Ulrich S. Schubert

Molbank 2025, 2025(2), M2024; https://doi.org/10.3390/M2024 - 18 Jun 2025

Abstract

This work presents the synthesis and structural characterization of a novel type of biscyclometalated Ir(III) complex, which is equipped with two iodoethynyl moieties on its 2,2′-bipyridine (bpy) ligand. Iodoethynyl moieties represent prominent donor systems for the formation of supramolecular structures via halogen bonding [...] Read more.

This work presents the synthesis and structural characterization of a novel type of biscyclometalated Ir(III) complex, which is equipped with two iodoethynyl moieties on its 2,2′-bipyridine (bpy) ligand. Iodoethynyl moieties represent prominent donor systems for the formation of supramolecular structures via halogen bonding (X-bonding). The synthesis of bis(2-phenylpyridinato)-[4,4′-bis(iodoethynyl)-2,2′-bipyridine]iridium(III) hexafluorophosphate, (2)(PF₆), is straightforward and involves post-complexation iodination, thus expanding the already rich toolbox for performing “chemistry on the complex”. The formation of the iodoethynyl moieties was unequivocally proven by ¹H-NMR spectroscopy, ESI-TOF mass spectrometry, and single-crystal XRD analysis. Full article

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4 pages, 560 KiB

Open AccessShort Note

(Z)-2-(Bromomethyl)-3-(hydroxymethylene)-7-methoxy-5-methyl-2-(tribromomethyl)-4-chromanone

by Chein-Chung Lee and Yen-Ku Wu

Molbank 2025, 2025(2), M2023; https://doi.org/10.3390/M2023 - 16 Jun 2025

Abstract

An attempt to achieve the deprotonative bromination of a 2-methyl-3-formyl-chromenone with tetrabromomethane led to an unexpected bromo-tribromomethylation product. We report the synthesis and characterization of the title compound. Full article

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9 pages, 516 KiB

Open AccessShort Note

4,4-Dichloro-1,3-dithietane-2-one

by Tracy R. Thompson, William W. Brennessel, Erik S. Goebel, Matthew J. Turcotte and George Barany

Molbank 2025, 2025(2), M2021; https://doi.org/10.3390/M2021 - 13 Jun 2025

Abstract

The title compound, 4,4-dichloro-1,3-dithietane-2-one, was encountered when opening a commercial capped amber bottle labeled “thiophosgene” that had been stored in a cold room (4 °C) for decades without any special precautions. Treating it as an unknown, the structure was established by single crystal [...] Read more.

The title compound, 4,4-dichloro-1,3-dithietane-2-one, was encountered when opening a commercial capped amber bottle labeled “thiophosgene” that had been stored in a cold room (4 °C) for decades without any special precautions. Treating it as an unknown, the structure was established by single crystal X-ray analysis, and confirmed by ¹³C NMR, FTIR, melting behavior, and elemental analysis; its behavior under several mass spectrometric conditions was also examined. The dithietane appears to be a spontaneously formed cyclodimer of thiophosgene in which exactly one (not zero, not both) of the dichloromethylene moieties has been hydrolyzed to a carbonyl function. The relative long-term stability of the hydrolyzed dimer, along with a pathway back to thiophosgene, suggests that it might serve as a storage vehicle for toxic thiophosgene. Furthermore, as noted elsewhere, the title compound reacts with nucleophiles under mild aqueous conditions, suggesting that it may be a useful probe in chemical biology. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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9 pages, 2176 KiB

Open AccessShort Note

4-Methyl-N-(1-benzyl)-N’-(1-benzylidene)benzenesulfonohydrazide

by Leticia Almazán-Sánchez, Marco A. García-Eleno, Diego Martínez-Otero and Erick Cuevas-Yañez

Molbank 2025, 2025(2), M2022; https://doi.org/10.3390/M2022 - 13 Jun 2025

Abstract

4-Methyl-N-(1-benzyl)-N’-(1-benzylidene)benzenesulfonohydrazide is formed through a direct, solventless reaction between benzaldehyde tosylhydrazone and potassium carbonate, which is carried out using an eco-friendly grinding method. The NMR spectra of the compound are here described. The structure was unequivocally determined by X-ray [...] Read more.

4-Methyl-N-(1-benzyl)-N’-(1-benzylidene)benzenesulfonohydrazide is formed through a direct, solventless reaction between benzaldehyde tosylhydrazone and potassium carbonate, which is carried out using an eco-friendly grinding method. The NMR spectra of the compound are here described. The structure was unequivocally determined by X-ray analysis. As suggested by Hirshfeld surface analysis, the predominant intermolecular H-O interactions in this molecule are involved in crystal packing. Full article

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11 pages, 3378 KiB

Open AccessCommunication

[Palladium-decabismuth(4+)]-tetrakis(tetrachloridoaluminate) Cluster Compound, [Pd@Bi₁₀][AlCl₄]₄: Synthesis, Crystal Structure, and Electronic Structure

by S. M. Gayomi K. Samarakoon and Sviatoslav Baranets

Molbank 2025, 2025(2), M2020; https://doi.org/10.3390/M2020 - 9 Jun 2025

Abstract

Black, needle-like single crystals of [Pd@Bi₁₀][AlCl₄]₄ were synthesized in a one-pot reaction between PdCl₂, Bi, and BiCl₃ at 180 °C in the Lewis acidic ionic liquid (LAIL) medium [BMIm]Cl∙4.2AlCl₄ (BMIm = 1-n-butyl-3-methylimidazolium). [...] Read more.

Black, needle-like single crystals of [Pd@Bi₁₀][AlCl₄]₄ were synthesized in a one-pot reaction between PdCl₂, Bi, and BiCl₃ at 180 °C in the Lewis acidic ionic liquid (LAIL) medium [BMIm]Cl∙4.2AlCl₄ (BMIm = 1-n-butyl-3-methylimidazolium). Single-crystal X-ray diffraction revealed that the compound crystallizes in the triclinic space group P

\bar{1}

with the unit cell parameters a = 11.0233(5) Å, b = 26.1892(14) Å, c = 26.2687(14) Å, α = 90.842(2)°, β = 92.1940(10)°, γ = 91.164(2)°, closely matching its platinum-containing analog. The structure features pentagonal antiprismatic [Pd@Bi₁₀]⁴⁺ cluster cations charge-balanced by tetrahedral [AlCl₄]⁻ anions. Bonding and charge analysis reveal unoptimized Pd–Bi and strong Bi–Bi covalent interactions consistent with electronegativity trends and the previously reported host–guest model. Electronic structure calculations performed with the TB-LMTO-ASA program show that [Pd@Bi₁₀][AlCl₄]₄ exhibits semiconducting behavior, suggesting a bandgap opening of 0.71 eV. Full article

(This article belongs to the Section Structure Determination)

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9 pages, 2019 KiB

Open AccessShort Note

5,5′-Di((E)-buta-1,3-dien-1-yl)-2,2′,3,3′-tetramethoxy-1,1′-biphenyl

by Maria Antonietta Dettori, Davide Fabbri, Roberto Dallocchio and Paola Carta

Molbank 2025, 2025(2), M2018; https://doi.org/10.3390/M2018 - 6 Jun 2025

Abstract

Phenylbutanoids, commonly found in various medicinal plants, have attracted significant attention due to their remarkable biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects, as well as for their versatility as starting materials in organic synthesis. Among phenylbutanoids, phenyl-1,3-butadienes represent a unique class of [...] Read more.

Phenylbutanoids, commonly found in various medicinal plants, have attracted significant attention due to their remarkable biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects, as well as for their versatility as starting materials in organic synthesis. Among phenylbutanoids, phenyl-1,3-butadienes represent a unique class of conjugated dienes, characterized by a phenyl (C₆H₅) group attached to a 1,3-butadiene (-CH=CH-CH=CH₂) backbone. In this study, we synthesized the hydroxylated biphenyl 5,5′-di((E)-buta-1,3-dien-1-yl)-2,2′,3,3′-tetramethoxy-1,1′-biphenyl 1, closely related to its corresponding monomer 2, which is known for its broad range of pharmacological activities. The synthesis was carried out using microwave-assisted technologies. The structure of the synthesized compound was confirmed through elemental analysis, ¹³C-NMR, ¹H-NMR, and ESI-MS spectrometry. Furthermore, we computed this novel compound’s conformational energy profile (CEP), evaluating how its energy varies with changes in the dihedral bond angle. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

6 pages, 686 KiB

Open AccessCommunication

A Neutral Heteroleptic Cu(I) Complex with Diimine and Diphosphine Ligands

by Xiaojuan Sun, Ruilong Sheng, Marijana Petkovic, Jolanta Jaśkowska and Zhiqiang Wang

Molbank 2025, 2025(2), M2019; https://doi.org/10.3390/M2019 - 6 Jun 2025

Abstract

Developing organic luminescent materials with the advantages of low cost, high thermal stability, and strong emission performance is incredibly desirable. In this work, we synthesized a new neutral heteroleptic Cu(I) complex characterized by single-crystal X-ray diffraction, FT-IR, NMR, and MALDI-TOF-MS. The neutral heteroleptic [...] Read more.

Developing organic luminescent materials with the advantages of low cost, high thermal stability, and strong emission performance is incredibly desirable. In this work, we synthesized a new neutral heteroleptic Cu(I) complex characterized by single-crystal X-ray diffraction, FT-IR, NMR, and MALDI-TOF-MS. The neutral heteroleptic Cu(I) complex has a typical distorted tetrahedral configuration, and the complex molecules are connected into 1D chains via C-H···π interactions in crystal. Full article

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Graphical abstract

9 pages, 700 KiB

Open AccessCommunication

Novel Acid-Catalyzed Transformation of 1-Benzyl-3-Chloro-5-Hydroxy-4-[(4-Methylphenyl)Sulfanyl]-1,5-Dihydro-2H-Pyrrol-2-One

by Liliya S. Kosolapova, Elena Sh. Saigitbatalova, Liliya Z. Latypova, Marat F. Valiev, Darya P. Gerasimova and Almira R. Kurbangalieva

Molbank 2025, 2025(2), M2017; https://doi.org/10.3390/M2017 - 4 Jun 2025

Abstract

Nitrogen-containing heterocycles of 3-pyrrolin-2-one series are widely represented in natural and synthetic compounds, with a broad spectrum of pharmacological activity and considerable potential in medicinal and synthetic organic chemistry. In this communication, we report the previously unknown acid-catalyzed transformation of a N-substituted [...] Read more.

Nitrogen-containing heterocycles of 3-pyrrolin-2-one series are widely represented in natural and synthetic compounds, with a broad spectrum of pharmacological activity and considerable potential in medicinal and synthetic organic chemistry. In this communication, we report the previously unknown acid-catalyzed transformation of a N-substituted derivative of 3-pyrrolin-2-one that generates two types of heterocyclic moieties. The reflux of 1-benzyl-3-chloro-5-hydroxy-4-[(4-methylphenyl)sulfanyl]-1,5-dihydro-2H-pyrrol-2-one in toluene in the presence of catalytic amounts of H₂SO₄ resulted in the formation of a mixture of 1-benzyl-3-[(4-methylphenyl)sulfanyl]-1H-pyrrole-2,5-dione and 1-benzyl-7-methyl-1H-benzo[4,5]thieno[3,2-b]pyrrole-2,3-dione. The structures of four novel nitrogen-containing heterocycles were elucidated through IR, NMR spectroscopy and HRMS spectrometry. A new derivative of the fused tricyclic compounds, possessing benzo[b]thiophene and pyrrole-1,2-dione fragments, was also characterized by single-crystal X-ray diffraction. Full article

(This article belongs to the Collection Heterocycle Reactions)

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8 pages, 1150 KiB

Open AccessCommunication

Structural Characterization of 7-Chloro-4-(4-methyl-1-piperazinyl)quinoline Monohydrate

by Silvia Rizzato and Francesco Marinoni

Molbank 2025, 2025(2), M2016; https://doi.org/10.3390/M2016 - 2 Jun 2025

Abstract

The crystal structure of the hydrated form of 7-chloro-4-(4-methyl-1-piperazinyl)quinoline (BPIP) was determined by single-crystal X-ray diffraction analysis. This study revealed a one-dimensional supramolecular network stabilized by hydrogen bonding interactions between BPIP and water molecules. This compound represents one-half of a piperaquine [...] Read more.

The crystal structure of the hydrated form of 7-chloro-4-(4-methyl-1-piperazinyl)quinoline (BPIP) was determined by single-crystal X-ray diffraction analysis. This study revealed a one-dimensional supramolecular network stabilized by hydrogen bonding interactions between BPIP and water molecules. This compound represents one-half of a piperaquine molecule, a member of the 4-aminoquinoline class of antimalarial treatments, currently employed as a partner agent in modern combination therapies. As a simplified structural analog, BPIP can serve as a critical model system for probing the intermolecular interactions, physicochemical properties, and structural behavior of the parent compound. As a result, conducting a thorough solid-state characterization of BPIP is critical for gaining insight into its physical properties and verifying the material’s identity and purity. Full article

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Graphical abstract

9 pages, 1297 KiB

Open AccessCommunication

Near-Infrared Emitting Chiral Tetranuclear Erbium Cluster Containing Soft-Base Bisthiazolate Linkers

by Vasily A. Ilichev, Anton F. Rogozhin, Roman V. Rumyantcev, Georgy K. Fukin and Mikhail N. Bochkarev

Molbank 2025, 2025(2), M2015; https://doi.org/10.3390/M2015 - 29 May 2025

Abstract

A tetraerbium cluster containing soft-base dianionic 4,8-difluorobenzo [1,2-d:5,4-d′]bisthiazole-2,6-dithiol (H₂L) ligands, μ-OH, and coordinated 1,2-dimethoxyethane (DME) of the general formula {Er₄(μ-L)₄(μ-OH)₄(DME)₄} (1) was synthesized using [...] Read more.

A tetraerbium cluster containing soft-base dianionic 4,8-difluorobenzo [1,2-d:5,4-d′]bisthiazole-2,6-dithiol (H₂L) ligands, μ-OH, and coordinated 1,2-dimethoxyethane (DME) of the general formula {Er₄(μ-L)₄(μ-OH)₄(DME)₄} (1) was synthesized using a one-pot method. X-ray analysis revealed that 1 is an asymmetrical tetramer in which there are four μ₂-bridging bisthiazole ligands and four μ₂-bridging hydroxide anions per four erbium ions. The molecule of 1 has inherent chirality, and the geometry of intramolecular F…F short contacts implies the formation of a classical halogen bond. Upon excitation by a 375 nm diode laser, compound 1 shows the moderate metal-centered emission of Er³⁺ ions that peaked at 1530 nm. Full article

(This article belongs to the Section Structure Determination)

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7 pages, 717 KiB

Open AccessShort Note

Diisopropyl (E)-(1-Hydroxy-3-phenylallyl)phosphonate

by Andy I. Coker, Aidan P. McKay, David B. Cordes and Brian A. Chalmers

Molbank 2025, 2025(2), M2013; https://doi.org/10.3390/M2013 - 27 May 2025

Abstract

We report the synthesis and the molecular structure as determined by single-crystal X-ray diffraction of diisopropyl (E)-(1-hydroxy-3-phenylallyl)phosphonate. The compound was fully characterised by ¹H, ¹³C, and ³¹P NMR spectroscopy, IR spectroscopy, and Mass Spectrometry. Full article

(This article belongs to the Section Structure Determination)

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8 pages, 1277 KiB

Open AccessShort Note

trans-Dihydroxo[5,10,15,20-tetrakis(3-pyridinium)porphyrinato]tin(IV) Nitrate

by Nirmal Kumar Shee and Hee-Joon Kim

Molbank 2025, 2025(2), M2014; https://doi.org/10.3390/M2014 - 27 May 2025

Abstract

The treatment of trans-dihydroxo[5,10,15,20-tetrakis(3-pyridyl)porphyrinato]Sn(IV) or [Sn(OH)₂(TPyP)] with 1% nitric acid in a mixture of water and acetone resulted in the formation of an ionic complex 1 [Sn(OH)₂(TPy^HP)](NO₃)₄. Complex 1 was fully characterized [...] Read more.

The treatment of trans-dihydroxo[5,10,15,20-tetrakis(3-pyridyl)porphyrinato]Sn(IV) or [Sn(OH)₂(TPyP)] with 1% nitric acid in a mixture of water and acetone resulted in the formation of an ionic complex 1 [Sn(OH)₂(TPy^HP)](NO₃)₄. Complex 1 was fully characterized by ¹H NMR spectroscopy, elemental analysis, UV-vis spectroscopy, powder X-ray diffraction, fluorescence spectroscopy, FT-IR spectroscopy, and single-crystal X-ray crystallography. X-ray crystallographic analysis confirmed that each peripheral pyridyl N atom is protonated to form tetra-cationic species {Sn(OH)₂(TPy^HP)}⁴⁺ stabilized by four NO₃⁻ counter anions. Intermolecular hydrogen bonding interaction between axial hydroxo ligands leads to the formation of a 1D porphyrin array. Nitrate anions also involve hydrogen bonding interactions with axial hydroxo ligands and the peripheral pyridinium groups. Full article

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8 pages, 479 KiB

Open AccessCommunication

Synthesis of a New Bichalcone via Suzuki–Miyaura Coupling Reaction

by François-Xavier Toublet, Yves Champavier, Aurélie Lévêque, Catherine Fagnère and Christelle Pouget

Molbank 2025, 2025(2), M2012; https://doi.org/10.3390/M2012 - 26 May 2025

Abstract

Unlike the wide number of natural biflavonoids, natural bichalcones are a rare and even less studied class. Nevertheless, some of them have proved their interest in the fight against cancer through their cytotoxic activity against human tumor cell lines. The aim of this [...] Read more.

Unlike the wide number of natural biflavonoids, natural bichalcones are a rare and even less studied class. Nevertheless, some of them have proved their interest in the fight against cancer through their cytotoxic activity against human tumor cell lines. The aim of this study was to synthesize a novel bichalcone: 3′,3‴,4,4′,4″,4‴,5′,5‴-octamethoxy-2,3″-bichalcone 1. The most efficient synthetic pathway was the Suzuki–Miyaura reaction between a boronated chalcone and a brominated one. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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8 pages, 374 KiB

Open AccessShort Note

4-(8-Propyl-2,4-dithioxo-1,3-diazaspiro[4.5]decan-3-yl)spiro[1,5-dihydro-1,5-benzodiazepine-2,3′-indoline]-2′-one)

by Dimitar Stoitsov, Marin Marinov, Plamen Penchev and Neyko Stoyanov

Molbank 2025, 2025(2), M2011; https://doi.org/10.3390/M2011 - 23 May 2025

Abstract

A number of 1D and 2D NMR techniques, such as ¹H, ¹³C, DEPT 135, ¹H-¹H COSY, HSQC, and HMBC, were utilized for the structure verification of 4-(8-propyl-2,4-dithioxo-1,3-diazaspiro[4.5]decan-3-yl)spiro[1,5-dihydro-1,5-benzodiazepine-2,3′-indoline]-2′-one). The NMR spectra provided evidence for the tautomeric conversion of the [...] Read more.

A number of 1D and 2D NMR techniques, such as ¹H, ¹³C, DEPT 135, ¹H-¹H COSY, HSQC, and HMBC, were utilized for the structure verification of 4-(8-propyl-2,4-dithioxo-1,3-diazaspiro[4.5]decan-3-yl)spiro[1,5-dihydro-1,5-benzodiazepine-2,3′-indoline]-2′-one). The NMR spectra provided evidence for the tautomeric conversion of the compound. The completely assigned NMR data was supported additionally by ATR. Full article

(This article belongs to the Section Structure Determination)

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12 pages, 1408 KiB

Open AccessCommunication

Synthesis of Mesoionic 1,3,4-Thiadiazole-2-Thiolates

by Sean Ray Kahnert and Andreas Schmidt

Molbank 2025, 2025(2), M2010; https://doi.org/10.3390/M2010 - 22 May 2025

Abstract

A reliable synthesis of C5-unsubstituted 1,3,4-thiadiazole-2-thiolates is described that avoids potentially explosive or laborious steps. This work presents a reliable method for preparing the starting material dithioformate from carbon disulfide and potassium or sodium tri-sec-butylhydroborates for the preparation of the mesoionic [...] Read more.

A reliable synthesis of C5-unsubstituted 1,3,4-thiadiazole-2-thiolates is described that avoids potentially explosive or laborious steps. This work presents a reliable method for preparing the starting material dithioformate from carbon disulfide and potassium or sodium tri-sec-butylhydroborates for the preparation of the mesoionic title compounds with potassium hydrazinecarbodithioates. New 1,3,4-thiadiazole-2-thiolates are presented, and missing structural analysis data of known derivatives are added (1D- and 2D-NMR, HR-ESI-MS, IR). Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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