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Study of Cyclization of Chelating Compounds Using Electrospray Ionization Mass Spectrometry

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Abstract

Electrospray ionization mass spectrometry (ESI-MS) was used for the study of cyclization of organic chelating compounds (chelators). Four chelating compounds were studed: Symmetrical ethylenediaminediacetic acid (s-EDDA), Unsymmetrical ethylenediaminediacetic acid (u-EDDA), N-(2-hydroxyethyl) ethylenediaminetriacetic acid (HEDTA), and N-(2-hydroxyethyl)iminodiacetic acid (HEIDA). The chelators were cyclized with treatments of acids and heating. The open and cyclized form of the chelators were semi-quantified by both positive and negative ion modes ESI-MS. The kinetics of chelator cyclization was studied as a function of reaction temperature and the pH of the matrix. The cyclization of s-EDDA was found to be a pseudo-first order reaction in s-EDDA and overall second order. The cyclizations of HEIDA and HEDTA are reversible reactions. Higher temperature and lower pH favors cyclization.

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Authors and Affiliations

  1. Battelle, Pacific Northwest National Laboratory, P.O. Box 999, Richland, Washington, 99352, USA

    Ying Shi

  2. Battelle, Pacific Northwest National Laboratory, P.O. Box 999, Richland, Washington, 99352, USA

    J. A. Campbell

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  1. Ying Shi
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  2. J. A. Campbell
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Shi, Y., Campbell, J.A. Study of Cyclization of Chelating Compounds Using Electrospray Ionization Mass Spectrometry. Journal of Radioanalytical and Nuclear Chemistry 245, 293–300 (2000). https://doi.org/10.1023/A:1006750102833

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