Nitrogen-bound diazeniumdiolated amidines.

Chemical Communications 46(31):5799 (2010) PMID 20589293

In contrast to amidines bearing ionizable alpha-CH bonds, which react with nitric oxide (NO) to add diazeniumdiolate groups at their alpha-carbons, benzamidine forms an N-bound diazeniumdiolate that can be further derivatized at the other amidine nitrogen and/or the terminal oxygen to form caged NO compounds as potential NO prodrugs.

DOI: 10.1039/c0cc00849d