Synthesis and Structural Investigation of Some Electron-Rich Nitroaromatics

White, Jonathan M.; Skene, Colin; Deadman, John; Epa, Ruwan; Foenander, Sarah; Hamer, Kyle; Fellowes, Thomas; Lim, S. Fern; Marcuccio, Sebastian M.; Martin, Roger F.

doi:10.1071/ch18523

Cited by 5 publications

(3 citation statements)

References 15 publications

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“…The molecular structure exhibits virtual C S point group symmetry with an r.m.s. deviation of 0.06 Å. Interestingly, the morpholino analogue of 1 likewise shows a nearly C S -symmetric structure in the crystal but with the 4-nitrophenyl group occupying a quasi equatorial position on the morpholine ring [17][18][19]. The structure overlay plot shown in Figure 1b illustrates the difference.…”

Section: Solid-state Structurementioning

confidence: 94%

Structural Characterization of 4-(4-Nitrophenyl)thiomorpholine, a Precursor in Medicinal Chemistry

Palme,

Goddard,

Imming

et al. 2024

Molbank

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4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title compound by means of a nucleophilic aromatic substitution reaction of 4-fluoronitrobenzene and thiomorpholine and structurally characterized it by X-ray crystallography, DFT calculations, and Hirshfeld surface analysis. In the crystal, the molecule exhibits an approximately CS-symmetric structure, with the nitrogen-bound 4-nitrophenyl group in a quasi axial position on the six-membered thiomorpholine ring in a low-energy chair conformation. The solid-state structure of the title compound is markedly different from that of its morpholine analogue. This can be ascribed to the formation of centrosymmetric dimers through intermolecular C–H···O weak hydrogen bonds involving the methylene groups adjacent to the sulfur atom and face-to-face aromatic stacking.

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Section: Solid-state Structurementioning

confidence: 94%

Structural Characterization of 4-(4-Nitrophenyl)thiomorpholine, a Precursor in Medicinal Chemistry

Palme,

Goddard,

Imming

et al. 2024

Molbank

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“…Nitrobenzene derivatives 8, 12, and 14 were prepared as previously described in the literature or obtained commercially. 28 Diethyl ditelluride was prepared according to the method of Levanova et al 29 General procedure for the catalytic reduction of nitrobenzenes 8 and 12. Palladium on carbon (5% w/w, 0.30 g) was added to a solution of the appropriate nitrobenzene (7.4 mmol) in ethanol (100 mL) and stirred under hydrogen (1 atm) for 18 h. The mixture was filtered through celite under an argon atmosphere, rinsing with ethanol.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and evaluation of benzochalcogenazole-benzimidazole derivatives as potential DNA-binding radioprotectors

White¹,

Fellowes²,

Skene³

et al. 2022

Arkivoc

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Benzothiazole 6 and benzoselenazole 7, which are closely related to the bisbenzimidazole radioprotector bisbenzimidazole M2PB 20, were prepared by reaction of a common amide intermediate 13O with Lawesson's and Woolin's reagents, respectively. A simpler tellurazole derivative 19 was prepared using a different synthetic strategy. The DNA binding affinity of the three chalcogenazoles 6, 7, 19 and the parent benzimidazole 20 were assessed by means of spectrophotometric DNA titration experiments using 16-mer oligonucleotides with and without a single binding site. While M2PB 20 shows clear binding to the oligonucleotide containing an AATT binding site, no strong conclusions can be made regarding the interactions of 6, 7 or 19 with DNA, either in the presence, or absence of an AATT binding site. Fluorescence microscopy studies with HeLa cells clearly shows nuclear localisation of M2PB (20); fluorescence is almost exclusively in nuclei. By contrast, for the benzoselenazole 7, fluorescence is excluded from the nuclei. These results suggest that the proposed chalcogen bonding interactions involving S, Se and Te in 6, 7, and 20 are not strong enough to impart the DNA binding behavior which is displayed by corresponding bis-benzimidazoles such as 20.

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“…The authors have cited additional references within the Supporting Information. [29][30][31][32][33][34][35][36][37][38][39][40][41]…”

Section: Theoretical Descriptionmentioning

confidence: 99%

Azotriptycenes: Photoswitchable Molecular Brakes

Stockerl,

Reißenweber,

Gerwien

et al. 2023

Chemistry A European J

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The control of molecular motions is a central topic of molecular machine research. Molecular brakes are fundamental building blocks towards such goal as they allow deliberately decelerating specific motions after an outside stimulus is applied. Here we present azotriptycenes as structural framework for light‐controlled molecular brakes. The intrinsic kinetics and their changes upon azotriptycene isomerization are scrutinized comprehensively by a mixed theoretical and variable temperature NMR approach. With azotriptycenes C‐N bond rotation rates can be decelerated or accelerated reversibly by up to five orders of magnitude. Rate change effects are highly localized and are strongest for the C‐N bond connecting a triptycene rotor fragment to the central diazo group. The detailed mechanistic insights provide a solid basis for further conscious design and applications in the future.

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Synthesis and Structural Investigation of Some Electron-Rich Nitroaromatics

Cited by 5 publications

References 15 publications

Structural Characterization of 4-(4-Nitrophenyl)thiomorpholine, a Precursor in Medicinal Chemistry

Structural Characterization of 4-(4-Nitrophenyl)thiomorpholine, a Precursor in Medicinal Chemistry

Synthesis and evaluation of benzochalcogenazole-benzimidazole derivatives as potential DNA-binding radioprotectors

Azotriptycenes: Photoswitchable Molecular Brakes

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