Aminomalononitrile (AMN) is the organic compound with the formula . The compound can be viewed as an amine-substituted malononitrile. It is of some interest to the study of the chemical
origin of life
Abiogenesis is the natural process by which life arises from abiotic component, non-living matter, such as simple organic compounds. The prevailing scientific hypothesis is that the transition from non-living to organism, living entities on ...
because it represents a trimer of
HCN, speculated to be a progenitor of nucleic acids. Aminomalononitrile has been prepared by reduction of the
oxime
In organic chemistry, an oxime is an organic compound belonging to the imines, with the general Chemical formula, formula , where R is an organic Side chain, side-chain and R' may be hydrogen, forming an aldoxime, or another organic functional g ...
: with
aluminium amalgam. The compound is used in situ but can be isolated as its
tosylate
In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or TosIn this article, "Ts", unless otherwise stated, means tosyl, not tennessine.) is a univalent functional group with the chemical formula . It consists of a tolyl ...
salt where
-OTs is .
[{{cite journal , last1=Ferris, first1=J. P., last2=Sanchez, first2=R. A., last3=Mancuso, first3=R. W., doi=10.15227/orgsyn.048.0001 , title=Aminomalononitrile p-Toluenesulfonate , journal=Organic Syntheses , date=1968 , volume=48 , page=1 ]
:
AMN reacts with cyanide to give
diaminomaleonitrile, a
tetramer
A tetramer () (''tetra-'', "four" + '' -mer'', "parts") is an oligomer formed from four monomers or subunits. The associated property is called ''tetramery''. An example from inorganic chemistry is titanium methoxide with the empirical formula ...
of HCN:
:
This easy conversion has been the source of some confusion.
References
Nitriles
Amines