Abstract
The mechanism of the conversion of secondary amines by sodium hypochlorite (NaOCl) to compounds that form fluorescent adducts with ο-phthalaldehyde (OPA)/2-mercaptoethanol (ME) was investigated by analyzing the reaction mixtures of secondary amines and NaOCl by high performance liquid chromatography (HPLC) and high performance thin-layer chromatography (HPTLC). Methylamine was found to be produced from N-methylamino acids, L-epinephrine, DL-metanephrine and N-methylcyclohexylamine. While N-phenylbenzylamine and N-alkylbenzylamines gave aniline and the corresponding alkylamines, respectively, N-alkylanilines produced the corresponding alkylamines rather than aniline. α-Amino acids were converted to ammonia by NaOCl. On the basis of these findings, mechanism of the conversion of secondary amines to primary amines by NaOCl were proposed.
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