5 years ago

Mechanistic and spectral investigation on the deamination of ammeline and ammelide

Mechanistic and spectral investigation on the deamination of ammeline and ammelide
Melamine and its metabolites: ammeline, ammelide, and cyanuric acid have attracted great attention as food contaminants. They are added illegally to milk to increase the protein content. Melamine combined with cyanuric acid causes kidney stones, renal toxicity, and kidney failure. The deamination reactions of ammeline and ammelide that producing cyanuric acid are studied both in a vacuum and aqueous solution using the (SMD) solvation model. For both deamination reactions, a two-step mechanism is formed: a nucleophilic addition yielding a tetrahedral intermediate that followed by a 1,3-proton shift to form products. The overall activation energies for deamination of ammeline with 3H2O/OH are 135, 121, 112, and 100kJmol−1 calculated in the vacuum by B3LYP, M06, M06-2X, and APFD combined with the 6-31G(d) basis set, respectively, and 129kJmol−1 calculated at G4MP2 level of theory. In comparison, the deamination reaction of ammelide shows lower energy barriers at all levels of theory (with the lowest values of 61kJmol−1 calculated at APFD/6-31G(d)). In addition, UV, IR, and 13C NMR spectral studies are performed and compared with the literature values.

Publisher URL: www.sciencedirect.com/science

DOI: S2210271X17303614

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.