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Schiff bases of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane and its silatranes: Synthesis and characterization

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Abstract

This paper aims at the introduction of azomethine group by the condensation reaction of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane with different compounds containing carbonyl group such as 2’-hydroxyacetophenone, salicylaldehyde, pyrrole-2-carboxaldehyde, acetylacetone and ethyl acetoacetate. Further, transesterification reaction of these Schiff base modified silanes with triethanolamine as a tripodal ligand leads to the synthesis of corresponding silatranes 15 bearing Schiff base functionalized long chain in the axial position. All the synthesized compounds are characterized by spectroscopic methods, elemental analysis and mass spectrometry. The authentication of Schiff base modified silatranes is scrutinized by single X-ray crystal structure of silatrane 1. The thermal stability of the five silatranes is studied by thermo-gravimetric analysis (TGA).

This paper reports the synthesis of Schiff base modified silanes by the condensation reaction of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane with compounds containing carbonyl group such as 2’-hydroxyacetophenone, salicylaldehyde, pyrrole-2-carboxaldehyde, acetylacetone and ethyl acetoacetate. The transesterification reaction of these Schiff base modified silanes with triethanolamine leads to the synthesis of corresponding Schiff base modified silatranes.

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Acknowledgments

The authors are thankful to University Grants Commission, New Delhi for providing financial support.

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Correspondence to GURJASPREET SINGH.

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Supplementary Information

CCDC 979226 contains supplementary crystallographic data for compound 1. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk. Supplementary data associated with this article can be found, in the online version, at www.ias.ac.in/chemsci.

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SINGH, G., SAROA, A., KHULLAR, S. et al. Schiff bases of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane and its silatranes: Synthesis and characterization. J Chem Sci 127, 679–685 (2015). https://doi.org/10.1007/s12039-015-0822-1

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  • DOI: https://doi.org/10.1007/s12039-015-0822-1

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