NMR and DSC studies on the reactions of pentanedioxy spiro-ansa cyclochlorotriphosphazene and pentanedioxy triple-bridged cylochlorotriphosphazene with monofunctional nucleophiles

Year 2019, Volume: 23 Issue: 6, 1177 - 1189, 01.12.2019

Rafig Gurbanov , Murat Tuna , Sedat Türe

https://doi.org/10.16984/saufenbilder.540276

Abstract

In this study, the reactions of 2-(2-hydroxyethyl) thiophene (2) and benzyl alcohol (3) with

pentanedioxycyclochlorotriphosphazene (1) and pentanedioxy triple-bridged cylochlorotriphosphazene (6)

were studied. The novel cyclotriphosphazene compounds: two di-substituted spiro-ansa, N 3 P 3 [O(CH 2 ) 5 O]-

(C 6 H 7 OS)] 2 (4) and N 3 P 3 [O(CH 2 ) 5 O-(C 6 H 5 CH 2 O)] 2 (5); and two fully substituted triple-bridged,

N 3 P 3 [O(CH 2 ) 5 O] 3 -(C 6 H 7 OS) 6 N 3 P 3 (7) and N 3 P 3 [O(CH 2 ) 5 O] 3 -(C 6 H 5 CH 2 O) 6 N 3 P 3 (8) derivatives were

formed in THF solvent by using NaH base at ambient conditions. Because of their variety of applications,

there is a great deal of interest in the preparation of aromatic macrocyclic derivatives of cyclophosphazenes.

The main purpose of these studies is to develop bioactive cyclophosphazene derivatives in the search for

new effective drug candidates for the treatment of various diseases, in particular, anticancer and

antimicrobials. The synthesized compounds (4, 5, 7, 8) were defined using analytical techniques namely

Element analysis, TLC/MS system, and NMR spectroscopy. Thermal stabilities, crystal purity, and

recrystallization properties and corresponding enthalpies of synthesized derivatives were analyzed in the

course of heating and cooling cycles of DSC.

Keywords

Cyclophosphazene, spiro-ansa compounds, triple-bridged compounds, monofunctional nucleophilic reagents, Nuclear magnetic resonance spectroscopy

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