Gaussian 16 density functional theory (DFT) calculation outputs supporting 'Selective Functionalisation of 5-Methylcytosine by Organic Photoredox Catalysis'

In this study, we report a xanthone-photosensitised process that introduces a 4-pyridine modification at a C(sp3)-H bond in the methyl group of 5-methylcytosine. We propose a reaction mechanism for this type of reaction based on density functional calculations and apply transition state analysis calculations to rationalise differences in observed reaction efficiencies between cyanopyridine derivatives. The reaction is initiated by single electron oxidation of 5-methylcytosine followed by deprotonation to generate the methyl group radical. Cross coupling of the methyl radical with 4-cyanopyridine installs a 4-pyridine label at 5-methylcytosine.

We present key DFT structures from the study in this dataset.