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Confirmation of the molecular structure of tetramethylene diperoxide dicarbamide (TMDD) and its sensitiveness properties
journal contribution
posted on 2023-05-18, 12:29 authored by Fitzgerald, M, Michael GardinerMichael Gardiner, Armitt, D, Gregory Dicinoski, Wall, CConjecture existed as to the molecular structure of the crystalline organic peroxide reaction product derived from the acidified aqueous mixture of urea, formaldehyde, and hydrogen peroxide. This study used X-ray crystal structure determination to unequivocally define the reaction product as the 14-membered ring structure tetramethylene diperoxide dicarbamide (TMDD). Crystals of TMDD belong to the monoclinic space group Pc, a = 4.587(4), b = 16.080(2), c = 6.690(5) Å, β = 107.44(5)°. The crystal contains one crystallographically independent molecule with approximate Cs symmetry. Intramolecular π-stacking of the carbonyl groups is a feature, while intermolecular H-bonding between the N–H and C═O functionalities affords linear polymeric strands that is associated with the extremely fine needle crystal morphology that necessitated synchrotron radiation for the structure determination. Sensitiveness testing examining susceptibility to initiate due to heat, impact, friction, and electrostatic stimuli was conducted to gauge the hazards associated with the material. It was revealed to be a primary explosive, particularly susceptible to impact initiation.
Funding
Dept of Prime Minister & Cabinet
History
Publication title
The Journal of Physical Chemistry Part AVolume
119Issue
5Pagination
905-910ISSN
1089-5639Department/School
School of Natural SciencesPublisher
Amer Chemical SocPlace of publication
1155 16Th St, Nw, Washington, USA, Dc, 20036Rights statement
© 2015 American Chemical SocietyRepository Status
- Restricted