SYNTHESIS AND THE SPECTRAL INVESTIGATIONS OF N-PYRIDINYL- SPIRO -PHOSPHAZENES

1. Hakan Dala, Yasemin Süzena, Zeynel Kılıçb and Tuncer Hökelekc a Department of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, TURKEY b Department of Chemistry, Faculty of Science, Ankara University, 06100 Tandoğan, Ankara, TURKEY c Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, TURKEY Abstract The condensation reactions of N-(2-hydroxyphenylmethyl)amino-methylpyridines (4-6) with trimer, N3P3Cl6, afford partially substitued novel spiro-cyclic phosphazene derivatives (7-9). The fully substitued phosphazenes (10 and 11) have also been obtained from the reactions of (9) with the excess of pyrrolidine and morpholine. The solid state structure of (8) has been determined by X-ray crystallography. The spectral investigations of all the compounds have been made by FT-IR, 1H-,13C-, 31P-NMR, HETCOR and MS. Introduction Cyclophosphazenes are an important family of inorganic ring systems, which traditionally have attracted attention for two main reasons: (i) to obtain small molecules of phosphazen derivatives, (ii) and to produce polymeric phosphazene derivatives . They also play an important role in the chemistry of heteroatom compounds. In resent years, phosphazene polymers have attracted considerable attention because they can be tailored to possess a wide variety of physical and chemical properties by changing the side groups [1]. The coordination chemistry of the various multi-site ligands derived from cyclophosphazenes is extremely interesting new area. Phosphazenes have been proposed for a broader array of applications including flame-retardants [2], rechargeable lithium batteries microencapsulant membranes, high performance fluids and ionic conductors, the further design of the highly selective anticancer, antibacterial, anti-HIV and artificial bone [3] agents. SYNTHESIS AND THE SPECTRAL INVESTIGATIONS OF N-PYRIDINYL-SPIRO-PHOSPHAZENES 1H-NMR Spectrum in δ 1-8 ppm. for a: Compound 10 and b: Compound 11 13C-NMR Spectrum in 10-160 ppm for 11 Scheme 31P-NMR Spectrum a: Compound 10 and b: Compound 11 HETCOR Spectrum of (11) Selected IR Bands The conformations of (a) the spirocyclic system and (b) The six-membered N/O ring in 8 An ORTEP-3 drawing of 8, with the atom-numbering scheme HMBC Spectrum of (11) The possible stereoisomer structure of compound 11at ambient temperaturein CDCl3 HMBC correlations for 11 • V. Chandrasekhar, K.R. Justin Thomas, Struct. Bonding. 81 (1993) 41. • J.E. Mark, H.R. Allcock, R.West, Inorganic Polymers; Printince-Hall, Englewood Cliffs, NJ 1992 • Nair, Lakshmi S.; Lee, Duron; Laurencin, Cato T. Polyphosphazenes as novel biomaterials.Handbook of Biodegradable Polymeric Materials and Their Applications 1 (2006) 277 Contact: hakandal@anadolu.edu.tr