Derivatization of 3-aminopropylsilatrane to introduce azomethine linkage in the axial chain: Synthesis, characterization and structural studies

Singh, Raghubir; Mutneja, Ruchi; Kaur, Varinder; Wagler, Jörg; Kroke, Edwin

doi:10.1016/j.jorganchem.2012.11.009

Cited by 26 publications

(9 citation statements)

References 11 publications

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“…The reaction of the carbonyl group with the 3-aminopropylsilyl group is very well known in literature. [61][62][63] The PXRD patterns of (Figure 2b). The identical peaks in the X-ray diffraction patterns after modification of magnetic nanosilica indicated that the crystalline nature of the particles persisted even after the incorporation of silica and copper complex.…”

Section: Surface Functionalization Aspectsmentioning

confidence: 99%

Dichiral [4.4.3.0^1,5]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects

Singh

Taya

Agarwal

et al. 2020

Applied Organom Chemis

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Pseudo-atranes have a significant role in catalysis; however, obtaining chiral pseudo-atranes for covalent functionalization of heterogeneous catalytic surfaces is very challenging. Herein, synthesis of a chiral tripodal amine [N{CH (CH 2 Ph)CH 2 OH}{CH 2 (4 Br C 6 H 3 OH)}{CH 2 (2 CHO 4 Me C 6 H 2 OH)}] (1) and a dichiral [4.4.3.0 1,5 ]tridecane copper(II) cluster, that is, (Cu[N{CH (CH 2 Ph)CH 2 OH}{CH 2 (4 Br C 6 H 3 O)}{CH 2 (2 CHO 4 Me C 6 H 2 O)}]) 2 (2) is described. The compounds are characterized by elemental analyses, Fourier transform infrared (FT-IR) spectroscopy, mass spectrometry and single-crystal X-ray crystallography (for 2). The compound 2 is the first example of chiral pseudo-copper(II)atrane in which three unsymmetrical arms (two phenolic and a chiral ethanolic arm) are fused via Cu N transannular bond. The free CHO group present in one of the tricyclic arms of the 2 is tested as a linker to load it on 3-aminopropyltriethoxysilane-functionalized magnetic nanosilica for catalytic applications. The loading of 2 on magnetic nanosilica through CHO was confirmed by FT-IR spectroscopy, and the 2-loaded magnetic nanosilica (Fe 3 O 4 @SiO 2 /2) was characterized by powder X-ray diffraction, vibrating sample magnetometry, scanning electron microscopy, energydispersive X-ray spectroscopy and elemental mapping. The Fe 3 O 4 @SiO 2 /2 was found highly efficient, retrievable, eco-friendly and green catalyst for obtaining β-amino alcohols in excellent yields in an aqueous medium. Overall, present work is the first report on synthetic, structural and catalytic aspects of dichiral cluster of copper(II)atrane possessing unsymmetrical tricyclic arms. K E Y W O R D S bisphenolate, pseudo-atrane, functionalized magnetic silica, unsymmetrical tripod, epoxide ringopening [Correction added on 4 November 2020, after first online publication: The three chemical structures in the first two rows of Table 4 were transposed and are now placed correctly.]

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Section: Surface Functionalization Aspectsmentioning

confidence: 99%

Dichiral [4.4.3.0^1,5]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects

Singh

Taya

Agarwal

et al. 2020

Applied Organom Chemis

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“…Functionalization of silatranes with different groups in exocyclic position is an important trend as the resulting compounds retain the activities of silatranes as well as substituted groups …”

Section: New Silatranes and Their Analogsmentioning

confidence: 99%

“…For example, silatranes. Due to their unusual architecture (the N → Si bond, the pentacoordinated silicon atom, the tricyclic structure), high dipole moment and strong electron‐donating effect of the silatrane skeleton, silatranes are of interest not only as theoretical objects but also as important functional reagents, advanced materials (Si‐organic polyimide films, catalysts, optical probes, adhesion layers for nanoparticles), as well as physiologically and pharmacologically active compounds …”

Section: Introductionmentioning

confidence: 99%

New atranes and similar ionic complexes. Synthesis, structure, properties

Адамович

2019

Applied Organom Chemis

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“…The diverse biological activity of atrane systems depends on the nature of the substituents, and such compounds can be both effective immunostimulants and adaptogens, and immunosuppressants, thus providing a stimulating or inhibiting effect on the vital activity of micro- and macroorganisms [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. In addition, atranes are used as important functional reagents [ 11 , 12 , 13 , 14 , 15 ], catalysts for the formation of polyurethanes [ 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Mechanism of Reactions of 1-Substituted Silatranes and Germatranes, 2,2-Disubstituted Silocanes and Germocanes, 1,1,1-Trisubstituted Hyposilatranes and Hypogermatranes with Alcohols (Methanol, Ethanol): DFT Study

2020

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The mechanism of reactions of silatranes and germatranes, and their bicyclic and monocyclic analogues with one molecule of methanol or ethanol, was studied at the Density Functional Theory (DFT) B3PW91/6-311++G(df,p) level of theory. Reactions of 1-substituted sil(germ)atranes, 2,2-disubstituted sil(germ)ocanes, and 1,1,1-trisubstituted hyposil(germ)atranes with alcohol (methanol, ethanol) proceed in one step through four-center transition states followed by the opening of a silicon or germanium skeleton and the formation of products. According to quantum chemical calculations, the activation energies and Gibbs energies of activation of reactions with methanol and ethanol are close, their values decrease in the series of atranes–ocanes–hypoatranes for interactions with both methanol and ethanol. The reactions of germanium-containing derivatives are characterized by lower activation energies in comparison with the reactions of corresponding silicon-containing compounds. The annular configurations of the product molecules with electronegative substituents are stabilized by the transannular N→X (X = Si, Ge) bond and different intramolecular hydrogen contacts with the participation of heteroatoms of substituents at the silicon or germanium.

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Derivatization of 3-aminopropylsilatrane to introduce azomethine linkage in the axial chain: Synthesis, characterization and structural studies

Cited by 26 publications

References 11 publications

Dichiral [4.4.3.0^1,5]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects

Dichiral [4.4.3.0^1,5]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects

New atranes and similar ionic complexes. Synthesis, structure, properties

Mechanism of Reactions of 1-Substituted Silatranes and Germatranes, 2,2-Disubstituted Silocanes and Germocanes, 1,1,1-Trisubstituted Hyposilatranes and Hypogermatranes with Alcohols (Methanol, Ethanol): DFT Study

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Derivatization of 3-aminopropylsilatrane to introduce azomethine linkage in the axial chain: Synthesis, characterization and structural studies

Cited by 26 publications

References 11 publications

Dichiral [4.4.3.01,5]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects

Dichiral [4.4.3.01,5]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects

New atranes and similar ionic complexes. Synthesis, structure, properties

Mechanism of Reactions of 1-Substituted Silatranes and Germatranes, 2,2-Disubstituted Silocanes and Germocanes, 1,1,1-Trisubstituted Hyposilatranes and Hypogermatranes with Alcohols (Methanol, Ethanol): DFT Study

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Dichiral [4.4.3.0^1,5]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects

Dichiral [4.4.3.0^1,5]tridecane copper(II) cluster derived from a tripodal ligand having unsymmetrical podands and the linker: Synthesis, structure, surface grafting and catalytic aspects