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Synthesis, spectral properties, and antimicrobial activity of 2-arilamino-2,4,4,6,6-pentachloro-1,3,5,2λ5,4λ5,6λ5-triazatriphosphines and poly[bis(4-fluorophenylamino)phosphazene]

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Abstract

2-(4-Chloro and 4-fluorophenylamino)-2,4,4,6,6-pentachloro-1,3,5,2λ5,4λ5,6λ5-triazatriphosphinines and poly[bis(4-fluorophenylamino)phosphazene] were synthesized by reactions of 4-fluoroaniline and 4-chloroaniline with 2,2,4,4,6,6-hexachloro-1,3,5,2λ5,4λ5,6λ5-triazatriphosphinin and poly(dichlorophosphazene), respectively, in tetrahydrofuran under argon at −20°C, followed by heating under reflux. The products were isolated by column chromatography and were characterized by FTIR, NMR (1H, 13C, 31P), and mass spectra, termogravimetry, and high-performance liquid chromatography. Antimicrobial activity of the monomeric compounds and polymer against 9 bacteria and 5 yeast cultures was evaluated by the disk diffusion method in dimethyl sulfoxide relative to a number of commercial antibiotics and antifungal agents. Aminophosphazene derivatives exhibited a broad spectrum of activity against both Gram-positive and Gram-negative bacterial with a magnitude comparable to reference antimicrobial agents. The polymeric product turned out to be more potent than the monomeric compounds.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, 17100, Çanakkale, Turkey

    M. Yildiz & S. Yilmaz

  2. Department of Biology, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, 17100, Çanakkale, Turkey

    B. Dölger

Authors
  1. M. Yildiz
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  2. S. Yilmaz
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  3. B. Dölger
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Correspondence to M. Yildiz.

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Original Russian Text © M. Yildiz, S. Yilmaz, B. Dölger, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 12, pp. 1972–1977.

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Yildiz, M., Yilmaz, S. & Dölger, B. Synthesis, spectral properties, and antimicrobial activity of 2-arilamino-2,4,4,6,6-pentachloro-1,3,5,2λ5,4λ5,6λ5-triazatriphosphines and poly[bis(4-fluorophenylamino)phosphazene]. Russ J Gen Chem 77, 2117–2122 (2007). https://doi.org/10.1134/S1070363207120079

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  • DOI: https://doi.org/10.1134/S1070363207120079

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