Molecular interactions between electrophiles and nucleic acids. II—Raman and infrared spectra of adenine, adenine hydrochloride and the corresponding 1‐methyl derivatives in relation to tautomerism and mutagenic phenomena of bases of nucleic acids

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Abstract
The Raman and IR spectra of adenine (AH3) and of its derivatives adenine hydrochloride (AH4Cl), 1‐methyladenine (1MeAH2) and 1‐methyladenine hydrochloride (1MeAH3Cl) are discussed in relation to the mutagenic and carcinogenic activities that they display.The spectra give evidence for a shift of tautomeric stability from the aminic form, which is favoured in AH3, toward the iminic, or iminic‐derived form, in the derivatives AH4Cl, 1MeAH2 and 1MeAH3Cl.The different biological activities of this series of compounds, in particular the mutagenic and carcinogenic effects, can be interpreted in terms of different reactivites associated with the π electronic systems, and of a hydrogen‐bond coupling different from the canonical Watson–Crick type.