Related Experiment Video
Updated: Aug 10, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
A bidentate terephthalamide ligand, TAMmeg, as an entry into terephthalamide-containing therapeutic iron chelating
Kristy M Clarke Jurchen1, Kenneth N Raymond
1Department of Chemistry, University of California at Berkeley, California 94720-1460, USA.
Abstract:
A new bidentate 2,3-dihydroxyterephthalamide ligand, 2,3-dihydroxy-N,N'-bis(2-methoxyethyl)terephthalamide (TAMmeg), has been prepared. The ligand, its synthetic precursor 2,3-bis(benzyloxy)-N,N'-bis(2-methoxy-ethyl)-terephthalamide (BnTAMmeg), and its iron complex have been structurally characterized by X-ray diffraction. BnTAMmeg crystallizes in the monoclinic space group P2(1)/n with cell parameters a = 14.4976(14) A, b = 11.5569(11) A, c = 16.3905(16) A, beta = 113.621(1) degrees , and Z = 4. TAMmeg crystallizes in the monoclinic space group P2(1)/c with cell parameters a = 13.8060(36) A, b = 8.0049(21) A, c = 19.4346(50) A, beta = 106.855(4) degrees , and Z = 4. Fe[TAMmeg] crystallizes in the triclinic space group P with cell parameters a = 12.9565(14) A, b = 13.4514(14) A, c = 20.2092(21) A, alpha = 102.093(2) degrees , beta = 95.433(2) degrees , gamma = 101.532(2) degrees , and Z = 2. The aqueous protonation and ferric ion coordination chemistry of TAMmeg were examined using potentiometric and spectrophotometric methods. Proton association constants and iron complex formation constants for the ligand are as follows: log beta(011) = 10.32, log beta(012) = 16.49, log beta(110) = 17.9, log beta(120) = 32.1, and log beta(130) = 43.0. The ferric complex of TAMmeg is surprisingly stable for a bidentate terephthalamide iron complex. The only more-stable bidentate terephthalamide iron complex that has been reported contains a ligand with positively charged pendant arms.
More Related Videos
Related Concept Videos
Metal-Ligand Bonds
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
EDTA: Chemistry and Properties
Complexation Equilibria: The Chelate Effect
Complexometric Titration: Ligands
EDTA: Auxiliary Complexing Reagents
Masking and Demasking Agents
There are many masking agents, such as cyanide, fluoride, triethanolamine, thiourea, and 2,3-bis(sulfanyl)propan-1-ol (formerly 2,3-dimercapto-1-propanol), with the masking agent chosen based on the metal...

