Accession Number : ADA293969

Title :   Acidity and Basicidity of Nitro Substituted Imidazoles.

Descriptive Note : Technical rept.,

Corporate Author : ARMY ARMAMENT RESEARCH DEVELOPMENT AND ENGINEERING CENTER PICATINNY ARSENAL N J ARMAMENT ENGINEERING DIRECTORATE

Personal Author(s) : Vladimiroff, T.

PDF Url : ADA293969

Report Date : APR 1995

Pagination or Media Count : 16

Abstract : The antibiotic azomycin is 2-nitroimidazole. 2,4-dinitroimidazole has recently been found to be a fairly powerful yet stable explosive. The family of all nitro substituted imidazoles constitute an interesting series of molecules from both the biological and the energetic material points of view. Imidazole is a heterocyclic five membered ring with two nitrogen atoms in the ring. One of these nitrogens is bound to a hydrogen atom so that it can act as a proton donor. The other nitrogen can act as a proton acceptor. The molecule can therefore act as both an acid and a base. In this work the protonation and deprotonation energies for all the nitro substituted imidazoles are computed with several basis sets. The GAUSSIAN 92 set of programs is used and all computations are performed at the SCF level of theory. The geometry of all the structures are determined using gradient techniques and compared to experimentally obtained geometries when available. It is found that these materials become more acidic and less basic as the degree of nitration increases. jg

Descriptors :   *ACIDS, *BASES(CHEMISTRY), *IMIDAZOLES, *NITRO RADICALS, STABILITY, COMPUTATIONS, BIOLOGY, QUANTUM CHEMISTRY, MOLECULES, ATOMS, PROTONS, EXPLOSIVES, NITROGEN, HYDROGEN, SUBSTITUTES, ELECTRON ACCEPTORS, ENERGETIC PROPERTIES, GRADIENTS, ANTIBIOTICS, NITRATION, NITROGEN COMPOUNDS, HETEROCYCLIC COMPOUNDS.

Subject Categories : Organic Chemistry
      Pharmacology
      Inorganic Chemistry
      Physical Chemistry
      Quantum Theory and Relativity

Distribution Statement : APPROVED FOR PUBLIC RELEASE