EDTA is a hexaprotic acid (H₆Y²⁺) having the pK_a values given in the featured paper (1). Figure 1 shows a distribution diagram for the EDTA system (2). At the pH of normal waters, the predominant species have one or both of the nitrogen atoms protonated.

Complexation, however, requires that both nitrogens be deprotonated and it is generally assumed that the form that complexes with metal ions is Y⁴⁻. Structures of several forms of EDTA are included in the molecule collection (Figure 2). These structures are quite flexible having many conformations that are readily accessible at room temperature.

An introduction to EDTA chemistry leads to broader questions of metal ion chelation or sequestration. Related chelating agents included in the molecule collection are EGTA, DCTA, NTA, BAPTA, and DTPA. Molecular dynamics and Hartree–Fock calculations on BAPTA (Figure 2) confirm that many conformations, ranging from those with the phenyl rings parallel to one another, to more elongated forms, are essentially isoenergetic in room temperature aqueous solution (3).

Also included in the molecule collection are several crown ethers, an isophore (nonactin), and a cryptand. These not only provide students with a glimpse of the types of molecules being employed for metal ion sequestration but open a wide range of topics of current research in a variety of areas of inorganic, industrial, environmental, and biological chemistry.

Literature Cited

1. Belle-Oudry, Deirdre. J. Chem. Educ. 2008, 85, 1269–1270.
2. This figure is from an available spreadsheet (accessed July 2008).
3. A short movie of a low-level (MM2) molecular mechanics calculation on BAPTA—one picosecond in one femtosecond intervals at 298 K—is available (accessed July 2008).

The molecules added to the collection this month are EDTA, EGTA, DCTA, NTA, BAPTA, DTPA, several crown ethers, an isophore (nonactin), a cryptand, and Eriochrome Black T (a metal ion indicator).