Chemical Shift Tensors in Isomers of Adenine: Relation to Aromaticity of Purine Rings?

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Authors	MALIŇÁKOVÁ Kateřina NOVOSADOVÁ Lucie PIPÍŠKA Matej MAREK Radek
Year of publication	2011
Type	Article in Periodical
Magazine / Source	ChemPhysChem
MU Faculty or unit	Central European Institute of Technology
Citation
Web	DOI: 10.1002/cphc.201000657
Doi	http://dx.doi.org/10.1002/cphc.201000657
Field	Physical chemistry and theoretical chemistry
Keywords	solid-state NMR; density-functional theory; X-ray diffraction; nucleus-independent chemical shift; supramolecular cluster
Attached files	CPC11_12_379.pdf
Description	13C and 15N chemical shift tensors (CST) are measured, calculated, and compared for three N-benzyladenine isomers with an attempt to characterize differences in electron distribution in the purine ring related to the position of the substituent. Furthermore, the aromaticity of the purine rings is evaluated on the basis of nucleus-independent chemical shifts (NICS), and variations among the isomers are discussed. Both parameters indicate significant differences between the electronic properties of the N3-substituted compound and the N7/N9 pair of structures which can be viewed more generally as the reason for the different stabilities of the individual tautomers.
Related projects:	Proteins in metabolism and interaction of organisms with the environment Biomolecular centre