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Studies concerning the nitration of coronene.

Akhtar, Muhammad Ishaq. (1971) Studies concerning the nitration of coronene. Doctoral thesis, University of Surrey (United Kingdom)..

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Abstract

A complete reinvestigation of the nitration of coronene has been carried out, it having been found that the literature methods and descriptions were unreliable; the preparations of nitrocoronene, dinitrocoronene, trinitro-coronene, and hexanitrocoronene have been carefully studied and precise conditions of their preparations are reported. Nitrocoronene and dinitrocoronene were converted to tri-nitrocoronene and hexanitrocoronene by use of 85% nitric acid and fuming nitric acid respectively. Similarly, tri-nitrocoronene was transformed into hexanitrocoronene by treatment with fuming nitric acid. The infrared spectra of the various nitro derivatives and of the coronene-hexanitro-coronene complex have been discussed. Treatment of nitrocoronene, dinitrocoronene, and trinitrocoronene with phenylhydrazine provided the corresponding amines, which on acetylation with acetic anhydride in pyridine, at room temperature, gave the corresponding N-acetyl derivatives. On prolonged heating under reflux with an excess of acetic anhydride, NN-diacetyl derivatives of the amines were obtained. Oxidation of coronene with sodium dichromate in acetic acid at 118° gave corono-1,2-quinone. Nitrocoronene, on oxidation under similar reaction conditions, furnished nitrocorono-1,2-quinone, which being an ortho-quinone formed the corresponding quinoxaline derivative with o-phenylene-diamine. Corono-1,2-quinone on nitration with 75% nitric acid yielded a dinitrocorono-1,2-quinone, whilst with 85% nitric acid a trinitrocorono-1,2-quinone was formed. In an attempt to determine the orientation of the substituents of bis-(diacetylamino)coronene and hence diaminocoronene and dinitrocoronene, a study of dipole moments was made. The dipole moments of NN-diacetyl derivatives of aminocoronene and diaminocoronene were determined. For the evaluation of the orientation of the substituents within these compounds, the angle of the group moment of the NN-diacetylamino group with its axis of rotation has been calculated from the observed dipole moments of NN-diacetyl-aniline and NNN'N'-tetra-acetyl-p-phenylenediamine, and also from the observed dipole moments of NN-diacetyl-2-naphthylamine, and 2,7-bis-(diacetylamino)naphthalene. From a consideration of the dipole moment data, infrared and n. m. r. spectra, it has been suggested that the most likely structure for the dinitrocoronene mentioned above, is that of 1,5-dinitrocoronene. For trinitrocoronene although 1,4,5-, 1,4,8-, 1,5,9- and 2,3,7-trisubstitutions are probable, the most likely formula is felt to be the 2,3,7 -trinitrocoronene. For hexanitrocoronene a structure having one nitro group on each outer ring is indicated, likely structures are 1,3,6,7,9,12- and 1,3,5,7,9,12-hexanitrocoronene.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
NameEmailORCID
Akhtar, Muhammad Ishaq.
Date : 1971
Contributors :
ContributionNameEmailORCID
http://www.loc.gov/loc.terms/relators/THS
Additional Information : Thesis (Ph.D.)--University of Surrey (United Kingdom), 1971.
Depositing User : EPrints Services
Date Deposited : 22 Jun 2018 09:50
Last Modified : 06 Nov 2018 16:52
URI: http://epubs.surrey.ac.uk/id/eprint/847147

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