Prebiotic Chemistry of HCN Tetramerization by Automated Reaction Search

HCN oligomerization is considered to be one of the important pathways in chemical evolution. Nucleobases, aminoacids, and many other complex organic molecules can evolve through this pathway. We report an explorative study based on an automated reaction search method that avoids the cognitive bias present when searching chemical reaction space. We discuss the chemical space of the HCN dimer in detail, and the important trimers and tetramers are discussed briefly. A component-wise molecular-fingerprint-based methodology is proposed to identify molecular similarity. We present four different thermal routes to cis/trans-2,3-diaminomaleonitrile and 4-amino-1H-imidazole-5-carbonitrile, which are important intermediates in prebiotic chemistry.