3 years ago

Thermodynamic and orbital studies of the reactivity of amidine with phosphoryl chloride and thionyl chloride

Raoudha Abderrahim, Maroua Bourkhis, Sameh Ayadi

Abstract

Amidines belong to the family of organic superbases; they are generally considered among the strongest useful synthetic auxiliary bases and are widely used in the synthesis of N-heterocycles. In this present work, we have studied the thermodynamic and the orbital recovery of the cyclization reaction of N'-(1H-benzo[d]imidazol-2-yl)-N-cyclopentylacetamidine 1 towards two reagents: the phosphoryl chloride (POCl3) 2 and thionyl chloride (SOCl2) 3. We were particularly interested in studying the different reactivity of the different sites of attack of the N'-(1H-benzo[d]imidazol-2-yl)-N-cyclopentylacetamidine 1, using density functional theory calculations (DFT) with functional B3LYP and standard base 6-311G. We used all the gathered information either from the experimental results obtained for these reactions or from the theoretical study; to exemplify the reactivity of each active site in our amidine 1, among this particular type of reaction under controlled condition to finally elucidate the mechanism of the obtaining of N-heterocycles such as the [1,2a]benzimidazolo-1,3,5,2-triazaphosphorin-2-oxide 6 and the [1,2a]benzimidazolo-1,2,4,6-thiatriazin-1-oxide 7.

Publisher URL: https://link.springer.com/article/10.1007/s11224-017-0989-9

DOI: 10.1007/s11224-017-0989-9

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.