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Spectroscopic and thermal study of dialkyl (alpha-anilino-N-benzyl)phosphonates and their palladium(II) complexes

Spectroscopic (13C NMR, UV/VIS, IR, FAB-mass) and thermal (TG, DTA) studies of dialkyl (alpha-anilino-N-benzyl)phosphonates and their palladium(II) dichloride adducts have been carried out in order to determine structural and decomposition properties of these biologically active compounds. Thermal decomposition of the complexes occurs in two steps: dehalogenation along with ligand deesterification is followed by complex pyrolysis that leads to a mixture of Pd and P_2O_5. The main gas-phase fragmentation pathways consist of sequential losses of HCl giving arise the mono- and bis-orthometallated species, and these processes are in competition with the loss of the phosphonate ester groups. Investigations in solution by NMR and UV/VIS spectra have shown that complexes retain their integrity in chloroform, but dissociate very fast in DMSO and DMF solutions leaving free organophosphorus ligand. The spectral and thermal properties of the complexes with respect to their antitumor activity have been discussed

palladium chloride; anilinobenzylphosphonate; complex; thermal analysis; spectroscopy

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