<i>N</i>,<i>N</i>′-Substituted thioureas and their metal complexes: syntheses, structures and electronic properties

Al-Riyahee, Ali A. A.; Coles, Simon J.; Berry, Colin; Horrocks, Paul; Pope, Simon J. A.; Amoroso, Angelo J.

doi:10.1039/d1dt04091j

Cited by 4 publications

(2 citation statements)

References 47 publications

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“…The intuitively assumed preference for symmetrical structures of such chiral and periodical macrocycles should, in principle, correspond to the number of signals on the NMR spectra. − In general, the 1 H NMR spectra of urea derivatives have shown fewer sharp signals than their thiourea counterparts. The 1 H NMR spectra of the urea-derived trianglamines 1a – 2a might be considered simple.…”

Section: Resultsmentioning

confidence: 99%

“…Bearing in mind the importance of urea and thiourea moieties in catalysis and supramolecular chemistry, − and, on the other hand, the growing role of periodical macrocyclic systems in material chemistry, we have decided to expand the study on other representatives of trianglamine, isotrianglamine, and rhombamine families. As the further spectacular applications of this type of macrocycles in various fields of chemistry originated from basic research, this work is aimed at the structural study of the series of macrocyclic urea and thiourea derivatives by means of complementary experimental and theoretical methods.…”

Section: Introductionmentioning

confidence: 99%

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Unravelling Structural Dynamics, Supramolecular Behavior, and Chiroptical Properties of Enantiomerically Pure Macrocyclic Tertiary Ureas and Thioureas

2022

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The introduction of urea or thiourea functionality to the macrocycle skeleton represents an alternative way to control conformational dynamics of chiral, polyamines of a figure-shaped periodical structure. Formally highly symmetrical, these macrocycles may adapt diverse conformations, depending on the nature of an amide linker and on a substitution pattern within the aromatic units. The type of heteroatom X in the N−C(�X)−N units present in each vertex of the macrocycle core constitutes the main factor determining the chiroptical properties. In contrast to the urea-containing derivatives, the electronic circular dichroism of thioureas is controlled by the chiral neighborhood closest to the chromophore. The dynamically induced exciton couplet is observed when the biphenyl chromophores are present in the macrocycle core. In the solid state, the seemingly disordered molecules may create ordered networks stabilized by intermolecular S•••halogen, H•••halogen, and S•••H interactions. The presence of two bromine substituents in each aromatic unit in thiourea-derived trianglamine gives rise to a self-sorting phenomenon in the crystal. In solution, this particular macrocycle exists as a dynamic equimolar mixture of two conformational diastereoisomers, differing in the spatial (clockwise and counter clockwise) arrangement of the C−Br bonds. In the crystal lattice, macrocycles of a given handedness assemble into homohelical layers.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Unravelling Structural Dynamics, Supramolecular Behavior, and Chiroptical Properties of Enantiomerically Pure Macrocyclic Tertiary Ureas and Thioureas

2022

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Synthesis, spectral characteristics and molecular structure of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives

Pokotylo

Zadorozhnii

Kiselev

et al. 2023

Journal of Heterocyclic Chem

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In this work, we report the synthesis of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives based on acylated thioureas. The method for the preparation of 1,3,5‐oxadiazine derivatives is based on the reaction of dehydrosulfurization of the starting acylated thioureas under the action of dicyclohexylcarbodiimide (DCC) followed by the [4 + 2] cycloaddition reaction of another DCC molecule to the resulting intermediate carbodiimide. The structure of the obtained derivatives of 1,3,5‐oxadiazine was confirmed by 1H, 13C NMR, IR spectroscopy, mass spectrometry, and x‐ray diffraction analysis.

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Synthesis, structural characterization and catalytic application of zinc and cadmium sulfur complexes with imidazol-2-ylidene-N’-phenylthiourea ligand scaffold

Narvariya

Das²,

Jain³

et al. 2022

Polyhedron

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N,N′-Substituted thioureas and their metal complexes: syntheses, structures and electronic properties

Abstract: Six different N,N′-substituted thiourea ligands were synthesised and their coordination chemistry with Cu(i), Cu(ii), Ni(ii) and Zn(ii) was extensively studied to reveal interesting ligand reactivities, and potential biological activity.

Cited by 4 publications

References 47 publications

Unravelling Structural Dynamics, Supramolecular Behavior, and Chiroptical Properties of Enantiomerically Pure Macrocyclic Tertiary Ureas and Thioureas

Unravelling Structural Dynamics, Supramolecular Behavior, and Chiroptical Properties of Enantiomerically Pure Macrocyclic Tertiary Ureas and Thioureas

Synthesis, spectral characteristics and molecular structure of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives

Synthesis, structural characterization and catalytic application of zinc and cadmium sulfur complexes with imidazol-2-ylidene-N’-phenylthiourea ligand scaffold

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