A combined computational and experimental study of nitrilimines generated from 2,5-substituted tetrazoles
Michael Thoenen1,2, Aleksa Milosavljevic3, Paul Wenthold4
1School of Materials Science and Engineering, Purdue University, 701 W Stadium Ave, West Lafayette, IN, 47906, USA. dpiercey@purdue.edu.
Abstract:
Nitrilimines are useful chemical intermediates for the synthesis of a variety of nitrogen heterocycles for use in pharmaceuticals, energetics, and other energy storage applications. The limitations of these intermediates are explored here with a paired experimental and computational study into the viable substituents for their generation from 2,5-substituted tetrazoles. Nitrilimines generated via the loss of nitrogen gas from these tetrazoles are accessible with almost any substitution at the 5-position, with electron withdrawing groups aiding in their formation. The lack of an aryl or heteroaryl substituent at the 2-position of the tetrazole prevented nitrilimine formation in all experiments, an observation that was supported by computation.
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