1. Thermal behaviour of sym-octahydroacridines and their corresponding N(10)-oxides.
- Author
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Marinescu, Maria, Potmischil, Francisc, Florea, Mihaela, and Constantinescu, Catalin
- Subjects
THERMAL analysis ,ACRIDINE ,NITROGEN oxides ,HYDROXYL group ,DISSOCIATION (Chemistry) - Abstract
We present and discuss results on the thermal behaviour of 1,2,3,4,5,6,7,8-octahydroacridine (OHA), together with six 9-substituted congeners, i.e. R = -Br, -OCH, -NH, -NO, -OH, and furyl (-CHO), and their corresponding N(10)- oxides, under nitrogen atmosphere and with alumina as reference, at a heating rate of 5 °C min from room temperature to 300 °C. Chromatography has been carried out on aluminium sheets, with aluminium oxide 60 F254 neutral (Merck). Melting effects are observed for almost all compounds in their corresponding curves, precisely determined by using a Boetius apparatus. Homolysis of the carbon-substituent bond occurs in most cases, a phenomenon which is consistent with the values of the bond dissociation energy. For all compounds, except for hydroxyl congeners, thermal decomposition started with an endothermic peak. Octahydroacridines readily decompose into volatile products, an effect which correlates with their low melting points, while little amounts of residue remain in place of the aromatic amines compared to the N(10)-oxides. The presence of N-O bonds greatly influences the thermal stability of the compound, in the sense of increasing it compared with the parent amine. Quantitative studies of the decomposition products reveal that the melting points, the 9-position substituent, and N-O bond all play an important role upon the thermal behaviour. Mechanistic/kinetic pathways are also proposed as such results are important in further designing laser processing protocols, i.e. matrix-assisted pulsed laser evaporation (MAPLE) or laser-induced forward transfer (LIFT), for thin film deposition and/or device printing. [ABSTRACT FROM AUTHOR]
- Published
- 2018
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