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Studies related to the hexamine nitrolysis reaction.

Farminer, A. R. (1974) Studies related to the hexamine nitrolysis reaction. Doctoral thesis, University of Surrey (United Kingdom)..

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Abstract

The object of this work is to obtain a bettor understanding of the chemistry of the nitrolysis reaction of hexamine in nitric acid alone, this reaction giving primarily 3,5-dinitro-1,3,5-triasncyclohexane derivatives as final products. Aspects of the nitrolysis reactions of hexamine, some related quarternary derivatives, and 7-nitro-1,3, 5-triazaadamaniane in nitric acid and nitric acid/ammonium nitrate solution are investigated. The nitrosation, tosylation and mathylation reactions of 7-nitro-1,3,5-triazaadamantane are studied and found to be similar to those of hexamine. Preliminary variable temperature 1H NMR studies have been performed on the reactions of 1-methoxymothyl-3,5-dinitro-1,3,5-triazacyclohexane, 3,7-dinitro-1,3,5,7-tetraaaabicyclo(3.3.1)nonane and hexamine in nitric acid solution over the temperature range 243-303 K, in an attempt to follow the course of reaction and characterise the intermediates. In order to monitor these reactions the NMR characteristics of certain N-nitramines, N-nitrosamines, 1,3,5,7-tetraazabicyclo(3.3.1)nonaries, hexamine and derivatives are studied, for compounds from these classes may be expected to participate in the nitrolysis reactions. The nitrolysis reaction of 7-nitro-1,3,5-triazaadamantane gives either 1,3,7-triazabicyclo(3. 3. 1) nonane or 1,3,5-trinitro-1,3-diazacyclohexane derivatives as products. The nature of these products suggests that the mechanism of nitrolysis for this molecule occurs via a stepwise scission process. Due to similarities between the chemistry of hexamine and 7-nitro-1,3,5 -triazaadamantane, particularly with regards to the characteristics of the nitrolysis reaction, it is considered that the nitrolysis reaction of hexamine probably involves a similar mechanism. 1H, 13C, 14N NMR and INDO molecular orbital studies are performed on selected molecules from the classes of compounds considered in this work with a view to the elucidation of their electronic structures.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
NameEmailORCID
Farminer, A. R.
Date : 1974
Contributors :
ContributionNameEmailORCID
http://www.loc.gov/loc.terms/relators/THS
Additional Information : Thesis (Ph.D.)--University of Surrey (United Kingdom), 1974.
Depositing User : EPrints Services
Date Deposited : 22 Jun 2018 13:01
Last Modified : 06 Nov 2018 16:52
URI: http://epubs.surrey.ac.uk/id/eprint/847420

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