A long-range tautomeric effect on a new Schiff isoniazid analogue, evidenced by NMR study and X-ray crystallography

Tănase, Constantin; Drăghici, Constantin; Shova, Sergiu; Hanganu, Anamaria; Gál, Emese; Munteanu, Cristian V. A.

doi:10.1039/c8nj01680a

Cited by 2 publications

(1 citation statement)

References 45 publications

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“…Hemiaminal is a functional group found in several natural products and pharmaceuticals, 28 and it is used in synthesis to generate in situ reactive imines for specific reactions. 29 These compounds are also considered intermediates in the formation of imines from amines and carbonyls, so it cannot be ruled out that their isolation can be considered as the intermediate step in the rupture of the C2�N3 bond observed in some TSC 9 and hydrazone 30 complexes.…”

Section: Structures Of the Acetone And Chloroform Solvates Of [Recl(h...mentioning

confidence: 99%

Coordination Chemistry of Potentially S,N,N_py-Tridentate Thiosemicarbazones with the {Re(CO)₃}⁺ Fragment and Formation of Hemiaminal Derivatives

2022

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Nine potentially S,N,N py -tridentate thiosemicarbazones (HL) derived from pyridine-2-carbaldehyde or 1-(2pyridyl)ethanone have been prepared and fully characterized. The X-ray crystal structures of six of them and two hydrochlorides were determined and analyzed. The reaction of the [ReX-(CH 3 CN) 2 (CO) 3 ]/[ReX(CO) 5 ] (X = Cl and Br) precursors with these ligands yielded different kinds of compounds: the adducts [ReX(HL)(CO) 3 ], in which the ligands were S,Nbidentate; the trinuclear species [Re 3 Cl 2 (L 23 )(HL 23 )(CO) 9 ]; and the thiosemicarbazonate compounds [Re(L)(CO) 3 ], where the ligand is S,N,N py -tridentate. Besides, the reaction in methanol or ethanol of the thiosemicarbazones derived from aldehydes yielded S,N,N py -tridentate hemiaminal cationic [Re(HL OR )(CO) 3 ]X and neutral [Re(L OMe )(CO) 3 ] complexes after the coordinated ligand underwent addition of the alcohol group to the imine bond. The reactivity of the complex [ReX(HL)(CO) 3 ] in MeOH and NEt 3 led to the formation of dinuclear [Re 2 (L) 2 (CO) 6 ], where the thiosemicarbazonate is again S,N-bidentate. The influence that the substituents on the thiosemicarbazone ligands have on the stability of the complexes and the effect of the reaction medium on the resulting compounds have been analyzed.

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Section: Structures Of the Acetone And Chloroform Solvates Of [Recl(h...mentioning

confidence: 99%

Coordination Chemistry of Potentially S,N,N_py-Tridentate Thiosemicarbazones with the {Re(CO)₃}⁺ Fragment and Formation of Hemiaminal Derivatives

2022

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General Method for Quantitation of Organic Hydroperoxides

Beutner

Ayers

Chen

et al. 2020

Org. Process Res. Dev.

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The utility of peroxides in synthetic organic chemistry is tied to significant safety risks posed by their handling, storage, and disposal. Although guidelines exist, a lack of reliable methods for quantitation of low levels of these species has been a major impediment to establishing data-driven safety guidelines and protocols. This paper discloses a general and reliable liquid chromatography-ultraviolet (LC-UV)-based method for the detection of a wide range of commonly encountered organic hydroperoxides. The implications of this method for safety concerns around trace peroxides are also discussed, supported by modern thermochemical analysis.

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A long-range tautomeric effect on a new Schiff isoniazid analogue, evidenced by NMR study and X-ray crystallography

Abstract: Isoniazid analogues were cyclized through acid catalysis by closing a THF ring, as favoured by Baldwin's rules (5-exo-trig).

Cited by 2 publications

References 45 publications

Coordination Chemistry of Potentially S,N,N_py-Tridentate Thiosemicarbazones with the {Re(CO)₃}⁺ Fragment and Formation of Hemiaminal Derivatives

Coordination Chemistry of Potentially S,N,N_py-Tridentate Thiosemicarbazones with the {Re(CO)₃}⁺ Fragment and Formation of Hemiaminal Derivatives

General Method for Quantitation of Organic Hydroperoxides

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A long-range tautomeric effect on a new Schiff isoniazid analogue, evidenced by NMR study and X-ray crystallography

Abstract: Isoniazid analogues were cyclized through acid catalysis by closing a THF ring, as favoured by Baldwin's rules (5-exo-trig).

Cited by 2 publications

References 45 publications

Coordination Chemistry of Potentially S,N,Npy-Tridentate Thiosemicarbazones with the {Re(CO)3}+ Fragment and Formation of Hemiaminal Derivatives

Coordination Chemistry of Potentially S,N,Npy-Tridentate Thiosemicarbazones with the {Re(CO)3}+ Fragment and Formation of Hemiaminal Derivatives

General Method for Quantitation of Organic Hydroperoxides

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Coordination Chemistry of Potentially S,N,N_py-Tridentate Thiosemicarbazones with the {Re(CO)₃}⁺ Fragment and Formation of Hemiaminal Derivatives

Coordination Chemistry of Potentially S,N,N_py-Tridentate Thiosemicarbazones with the {Re(CO)₃}⁺ Fragment and Formation of Hemiaminal Derivatives