Conformational analysis and the binding sites of nitrilotriacetamide: A computational study

Authors

  • Ajeet Singh,

    1. Analytical Science Discipline, Central Salt and Marine Chemicals Research Institute, G. B. Marg, Bhavnagar, Gujarat 364002, India
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  • Shampa Chakraborty,

    1. Analytical Science Discipline, Central Salt and Marine Chemicals Research Institute, G. B. Marg, Bhavnagar, Gujarat 364002, India
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  • Bishwajit Ganguly

    Corresponding author
    1. Analytical Science Discipline, Central Salt and Marine Chemicals Research Institute, G. B. Marg, Bhavnagar, Gujarat 364002, India
    • Analytical Science Discipline, Central Salt and Marine Chemicals Research Institute, G. B. Marg, Bhavnagar, Gujarat 364002, India
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Abstract

The conformational analysis of nitrilotriacetamide has been carried out computationally, at both the semi-empirical AM1 and density functional theory (DFT) (B3LYP/6-31+G*) levels of theory. The lowest-energy conformation predicted with the Monte Carlo search method, using the AM1 model, has two amide functionalities aligned on the same side; however, the DFT calculations at B3LYP/6-31+G* predicted the global minimum with all three acetamide functionalities on the same side in the gas phase. In the aqueous phase, the DFT results predicted the orientations of amides similar to that of the reported crystal structure. The rotation barriers to transition to different low-energy conformers of nitrilotriacetamide are lower in energy (5.0 kcal/mol) in water. The molecular electrostatic isopotentials (MESP) generated for the selected conformers at DFT level show that the nitrilotriacetamide could interact more effectively with the sodium chloride surface than that of its monomeric unit nitrilomonoacetamide. © 2006 Wiley Periodicals, Inc. Int J Quantum Chem, 2007

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