A central problem in the field of astrochemistry is the formation of nucleobases and their analogues in the interstellar environment. Direct synthesis of these compounds in the gas phase is extremely complicated. However, by examining the reverse process of fragmentation, crucial information can be elucidated. These processes have been heavily studied for cation and radical nucleobases, yet anions remain without much investigation. Our research group has previously examined the fragmentation of deprotonated purine nucleobases adenine and guanine. This work presents an experimental and computational exploration of the fragmentation of a series of n-methylguanine anions. It is well known that variance in substituents can have a significant effect on bond strength. Thus, the investigation of substituted purines will provide further understanding of synthetic pathways to this class of compounds. Electrospray ionization (ESI) is employed to generate a series of deprotonated substituted biomolecules in a Thermo LCQ Deca XP Plus ion trap mass spectrometer. Collision induced dissociation (CID) experiments are then conducted within the ion trap instrument to observe the predominant fragmentation pathways of these species. To complement and quantify the energetics of these experimental observations, <i>Gaussian 09 </i>density functional theory calculations are performed.

Fragmentation of deprotonated n-methylguanine anions

255th National Meeting (2018)

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