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Nucleophilic Nitration of Selected Aza-Aromatics: Experiments and Modelling.

ADA396283

Publication Date	2001
Personal Author	Lochert, I. J.; Dorsett, H. E.
Page Count	27
Abstract	Nitration of isoquinoline and phthalazine has been successfully demonstrated using a novel process which does not require strong acids. In this study, nitration of isoquinoline was repeated and the method applied to 1- nitroisoquinoline and the aza-aromatics quinoline, quinazoline, quinoxaline and pyridine. Nitration of only quinoline was observed, with a product yield lower than that reported for nitration of isoquinoline. For 1-nitroisoquinoline and quinoxaline, the substrates were recovered essentially unchanged. For quinazoline and pyridine, neither the substrates nor any reaction products were isolated. In no case was multiple nitration detected. Thus, while the scope of the reaction is broader than initially reported, it is clearly not a universal method for nitrating aza-aromatics. Molecular modelling calculations have identified a correlation between the acidity of the intended nitration site and the observed yield, which might be used to screen potential substrates for this nitration technique.
Keywords	Quinolines Nitration Sites Substrates Yield Australia Reactants(Chemistry) Acids Quinoxalines Energetic materials Computational chemistry Molecular modelling Quantum theory Isoquinoline Foreign reports
Source Agency	Non Paid ADAS
Corporate Authors	Defence Science and Technology Organisation, Victoria (Australia). Aeronautical and Maritime Research Lab.
Document Type	Technical Report
Title Note	Technical note.
NTIS Issue Number	200206

Nucleophilic Nitration of Selected Aza-Aromatics: Experiments and Modelling.

Nucleophilic Nitration of Selected Aza-Aromatics: Experiments and Modelling.
ADA396283

Publication Date	2001
Personal Author	Lochert, I. J.; Dorsett, H. E.
Page Count	27
Abstract	Nitration of isoquinoline and phthalazine has been successfully demonstrated using a novel process which does not require strong acids. In this study, nitration of isoquinoline was repeated and the method applied to 1- nitroisoquinoline and the aza-aromatics quinoline, quinazoline, quinoxaline and pyridine. Nitration of only quinoline was observed, with a product yield lower than that reported for nitration of isoquinoline. For 1-nitroisoquinoline and quinoxaline, the substrates were recovered essentially unchanged. For quinazoline and pyridine, neither the substrates nor any reaction products were isolated. In no case was multiple nitration detected. Thus, while the scope of the reaction is broader than initially reported, it is clearly not a universal method for nitrating aza-aromatics. Molecular modelling calculations have identified a correlation between the acidity of the intended nitration site and the observed yield, which might be used to screen potential substrates for this nitration technique.
Keywords	Quinolines Nitration Sites Substrates Yield Australia Reactants(Chemistry) Acids Quinoxalines Energetic materials Computational chemistry Molecular modelling Quantum theory Isoquinoline Foreign reports
Source Agency	Non Paid ADAS
Corporate Authors	Defence Science and Technology Organisation, Victoria (Australia). Aeronautical and Maritime Research Lab.
Document Type	Technical Report
Title Note	Technical note.
NTIS Issue Number	200206