Novel 1,3-dipolar cycloadditions of dinitraminic acid: Implications for the chemical stability of ammonium dinitramide
2008 (English)In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 112, no 11, 2456-2463 p.Article in journal (Refereed) Published
Density functional theory at the B3LYP/6-31+G(d,p) level and ab initio calculations at the CBS-QB3 level have been used to analyze 1,3 dipolar cycloaddition reactions of dinitraminic acid (HDN) and its proton transfer isomer (HO(O)NNNO2). It is shown that the nitro group of HDN and the -N-N = O functionality of the isomer react readily with carbon-carbon double bonds. Cycloadditions of HDN are compared with the corresponding reactions with azides and nitrile oxides as 1,3 dipoles. It is shown that the reactivities of HDN and its proton transfer isomer decrease with increasing electron withdrawing power of the substituents adjacent to the carbon-carbon double bond. In contrast, for azides and nitrile oxides, the highest reactivity is obtained with dipolarophiles with strongly electron withdrawing substituents. The observed reactivity trends allow for the design of unsaturated compounds that are highly reactive toward azides and chemically inert toward dinitramides. This may be of relevance for the development of binder materials for ammonium dinitramide based propellants.
Place, publisher, year, edition, pages
2008. Vol. 112, no 11, 2456-2463 p.
IdentifiersURN: urn:nbn:se:kth:diva-17373DOI: 10.1021/jp710559gISI: 000253946100035ScopusID: 2-s2.0-46849106047OAI: oai:DiVA.org:kth-17373DiVA: diva2:335417
QC 201005252010-08-052010-08-052010-11-03Bibliographically approved