University of Tasmania
Browse

File(s) under permanent embargo

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, C
Conjecture 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 A

Volume

119

Issue

5

Pagination

905-910

ISSN

1089-5639

Department/School

School of Natural Sciences

Publisher

Amer Chemical Soc

Place of publication

1155 16Th St, Nw, Washington, USA, Dc, 20036

Rights statement

© 2015 American Chemical Society

Repository Status

  • Restricted

Socio-economic Objectives

National security

Usage metrics

    University Of Tasmania

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC