6-Mercaptopurine, 6MP, is a sulfur analogue of adenine which is commonly used as an antitumor agent.
The coordination chemistry of 6MP with metals is of interest because the drug contains a number of
electronically versatile binding sites. In this study the interaction between 6MP and a silver electrode
surface was investigated using surface-enhanced Raman spectroscopy (SERS). High-quality solution Raman
spectra of 6MP along with surface-enhanced Raman scattering spectra of 6MP adsorbed on a roughened
silver electrode surface are presented. Urey−Bradley force field and semiempirical calculations with the
PM3 method were used to generate vibrational frequencies for 6MP based on a specific set of possible
molecular interaction sites. An error analysis of the calculated frequencies and the experimentally determined
SERS frequencies allowed for the identification of the experimental data which most closely matched the
calculated SERS data. It was concluded that 6MP attaches head-on through the N1 atom when the molecule
is adsorbed onto a silver electrode surface.
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