Specific sequestering agents for the actinides. III. Polycatecholate ligands derived from 2,3-dihydroxy-5-sulfobenzoyl conjugates of diaza- and tetraazaalkanes

Journal Article · Wed Mar 26 04:00:00 EST 1980 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00527a026· OSTI ID:5279357

Weitl, F L; Raymond, K N

As part of a program to develop specific sequestering agents for the actinides, we have reported the synthesis of N,N',N'',N'''-tetra(2,3-dihydroxybenzoyl)tetraazacycloalkanes. These tetra(DHB) amodes are potentially octadentate ligands via coordination of the catechol oxygen atoms. We now report the synthesis of the DHB amides of linear tetraaza- and diazaalkanes. Furthermore, sulfonation of these compounds in 20 to 30% SO/sub 3/-H/sub 2/SO/sub 4/ yields exclusively their tetra(5-sulfo-DHB) analogues. The sulfonated derivatives have several properties which make them superior to their precursors with respect to actinide coordination; these properties include increased water solubility, enhanced phenolic acidity, and improved oxidative stability near neutral pH. In vivo tests with mice have shown that tetrameric (5-sulfo-DHB) compounds are generally acutely nontoxic, efficient sequestering agents for the actinides which promote rapid urinary excretion of /sup 238/Pu. The tetra(5-sulfo-DHB) derivative of spermine is more effective than any other plutonium sequestering agent yet tested. 4 figures, 1 table.

• Research Organization: Univ. of California, Berkeley
• DOE Contract Number: W-7405-ENG-48
• OSTI ID: 5279357
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 102:7; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702* -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
ACTINIDES
ALKANES
AMINES
ANIMALS
AROMATICS
BODY
CHELATING AGENTS
CHEMICAL REACTIONS
CRYOGENIC FLUIDS
CYCLOALKANES
DEVELOPERS
ELEMENTS
FLUIDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
IN VIVO
INORGANIC ACIDS
LIGANDS
MAMMALS
METALS
MICE
NONMETALS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANS
OXYGEN
PH VALUE
PHENOLS
PLUTONIUM
POLYPHENOLS
PYROCATECHOL
REMOVAL
RODENTS
SOLUBILITY
SPERMINE
SULFONATES
SULFURIC ACID
SYNTHESIS
TRANSURANIUM ELEMENTS
URINARY TRACT
VERTEBRATES