RCNHNHNH2

RCNHNHNH₂, commonly known as guanidine, is an organic compound with the chemical formula C(NH₂)₃NH₂. It is a colorless, hygroscopic solid that is highly soluble in water and polar solvents. Guanidine is notable for its strong basicity, which arises from the delocalization of its positive charge across three nitrogen atoms, making it one of the strongest organic bases known.

The structure of guanidine features a central carbon atom bonded to three nitrogen atoms, each of which carries a hydrogen atom. This arrangement contributes to its unique chemical properties, including its ability to stabilize positive charges and participate in various biochemical reactions. Guanidine derivatives are widely studied in organic chemistry due to their role in peptide synthesis, enzyme inhibition, and as superbase catalysts.

In biological systems, guanidine appears in naturally occurring compounds such as creatine and arginine, where it plays roles in energy metabolism and signaling pathways. Guanidine itself is not naturally abundant but is synthesized industrially for use in pharmaceuticals, agrochemicals, and specialty chemicals. Its strong basicity makes it useful in processes requiring high pH conditions, such as the deprotonation of weak acids.

Despite its utility, guanidine can be corrosive and toxic, requiring careful handling. It is often used in laboratory settings for its ability to denature proteins and disrupt hydrogen bonding, which is useful in techniques like protein refolding studies. Research into guanidine and its derivatives continues to explore applications in materials science, catalysis, and medicinal chemistry.