Phosphorus-nitrogen compounds: Part 43. Syntheses, spectroscopic characterizations and antimicrobial activities of cis- and trans-N/O dispirocyclotriphosphazenes containing ferrocenyl pendant arms

Tumer Y., ASMAFİLİZ N., Kilic Z., AYDIN B., AÇIK L., HÖKELEK T.

JOURNAL OF MOLECULAR STRUCTURE, vol.1173, pp.885-893, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1173
  • Publication Date: 2018
  • Doi Number: 10.1016/j.molstruc.2018.07.050
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.885-893
  • Keywords: Dispiroferrocenylphosphazenes, Spectroscopy, Chiral phosphazenes, Antimicrobial activity, Crystal structure, PIVOT ETHER DERIVATIVES, SPIRO-ANSA-SPIRO, DNA INTERACTIONS, BIOLOGICAL-ACTIVITIES, STRUCTURAL INVESTIGATIONS, CYTOTOXIC ACTIVITIES, ELECTROCHEMICAL INVESTIGATIONS, TRIBOLOGICAL PROPERTIES, CRYSTAL-STRUCTURE, PHOSPHAZENES
  • Ankara University Affiliated: Yes

Abstract

The cis- (5 and 6) and trans-dispiroferrocenylphosphazenes (7 and 8) containing ferrocenyl pendant arms were synthesized from the reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with two equimolar amounts of the sodium salts of the ligands; [2-(N-ferrocenylmethylamino)-1-ethanoxide (1) and 3-(N-ferrocenylmethylamino)-1-propanoxide (2)]. The monospiroferrocenylcyclotriphosphazenes (3 and 4) were also isolated from the reaction mixtures as by-products. The characterizations of the new compounds (5-8) were elucidated using MS, FTIR and H-1, C-13 and P-31 NMR techniques. The molecular structure of 6 was established by X-ray crystallography. As expected, compounds 5, 6, 7 and 8 have two stereogenic P-atoms. The compounds 5 and 6 are likely to be in cis (meso) forms, whereas the compounds 7 and 8 are in trans (racemic) forms. Besides, the antimicrobial activities of the cyclotriphosphazenes against G(+) and G(-) bacteria and fungi were evaluated. The interactions of the compounds with pBR322 plasmid DNA were also investigated. (C) 2018 Elsevier B.V. All rights reserved.