diaminomaleonitrile

plural diaminomaleonitriles · abbreviation DAMN

1. chemistryAn organic compound (C₄H₄N₄) used in the synthesis of several heterocyclic compounds.

   Diaminomaleonitrile (DAMN), a stable tetramer of HCN, has long been renowned as a precursor for the formation of nucleobases.

   2016, Yassin Aweis Jeilani, Phoenix N. Williams, Sofia Waltona, Minh Tho Nguyen, “Unified reaction pathways for the prebiotic formation of RNA and DNA nucleobases”, in Physical Chemistry Chemical Physics, volume 18, number 30, →DOI

   2 more examples

   Several nitrogen heterocycles, including imidazoles,¹⁻³ pyrazines,⁴ and diazepines,^(1, 3) have been prepared from diaminomaleonitrile (DAMN, 1), the tetramer of hydrogen cyanide.

   1978, Yozo Ohtsuka, “Chemistry of diaminomaleonitrile. 3. Reaction with isocyanate: a novel pyrimidine synthesis”, in Journal of Organic Chemistry, volume 43, number 16, page 3231

   The UV/Vis absorption spectra of the N,N′-disubstituted diaminomaleonitriles 1, 2 (Figure 1) and 3 (Figure S1 in the Supporting Information) in THF/H2O mixtures (1:1 v/v) show a charge transfer (CT) band of the push-pull diaminomaleonitrile electron system in the range of 280–350 nm.

   2012, Thomas Schwarze, Alexandra Kelling, Holger Müller, Michael Trautmann, Tillmann Klamroth, Otto Baumann, Peter Strauch, Hans-Jürgen Holdt, “N-2-Pyridinylmethyl-N′-arylmethyl-diaminomaleonitriles: New Highly Selective Chromogenic Chemodosimeters for Copper(II)”, in Chemistry Europe, volume 18, number 34, →DOI