Transition metal chemistry of main group hydrazides. Part 3:{sup 1} carboxylate appended phosphorus hydrazides as novel functionalized chelating systems. Synthesis and characterization of new cyclometallaphosphohydrazides. X-ray structure of a Palladium(II) representative
- Missouri Univ. Research Reactor, Columbia, MO (United States)
- Univ. of Missour, Columbia, MO (United States)
The synthesis of new bifunctional chelating agents (BFCAs) based on the phosphorus hydrazide ligand family for potential {sup 109}Pd labeling of tumor-localizing biomolecules such as proteins/peptides is described. The new BFCAs were achieved in good yields (75-90%) by the reaction of the phosphorus hydrazide PhP(S)(NMeNH{sub 2}){sub 2} (1) with functionalized aldehydes to yield the Schiff-base products with the following chemical compositions as air-stable crystalline solids: PhP(S)(NMeNH{sub 2})(NMeNCHC{sub 6}H{sub 4}COOH), 2; PhP(S)(NMeNCHC{sub 6}H{sub 4}COOH){sub 2}, 3; PhP(S)(NMeNH{sub 2})(NMeNCHC{sub 6}H{sub 4}CH=CHCOOH), 4; PhP(S)(NMeNCHC{sub 6}H{sub 4}CH-CHCOOH){sub 2}, 5. The reactions of three of the new phosphorus hydrazides (2-4) with PdCl{sub 2}(PhCN){sub 2} resulted in the new Pd(II) metallacycles PhP(S)(NMeNH{sub 2})(NMeNCHC{sub 6}H{sub 4}COOH){center_dot}PdCl{sub 2}, 6; PhP(S)(NMeNCHC{sub 6}H{sub 4}COOH){sub 2}{center_dot}PdCl{sub 2}, 7; and PhP(S)(NMeNH{sub 2})(NMeNCHC{sub 6}H{sub 4}CH=CHCOOH){center_dot}PdCl{sub 2}, 8. The reactivity of 6 toward n-butylamine has been evaluated as a model for the preparation of new bioconjugates. The structural elucidation of all the new compounds has been carried out by analytical and complete NMR ({sup 1}H, {sup 31}P) and IR spectroscopic data. As a representative example, the X-ray structure of one of the Pd(II) complexes, 8, has been determined.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 75742
- Journal Information:
- Inorganic Chemistry, Vol. 33, Issue 4; Other Information: PBD: 16 Feb 1994
- Country of Publication:
- United States
- Language:
- English
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