6533b82bfe1ef96bd128d802

RESEARCH PRODUCT

Aromaticity of the most stable adenine and purine tautomers in terms of Hückel's 4N+2 principle

Paulina H. MarekPaulina H. MarekAnna JezuitaHalina SzatylowiczTadeusz M. Krygowski

subject

PurineAromaticity010405 organic chemistryAdenineOrganic ChemistryAromaticityElectron010402 general chemistry01 natural sciencesBiochemistryTautomerTautomer0104 chemical sciencesHückel rulechemistry.chemical_compoundCharacter (mathematics)chemistryComputational chemistryDrug DiscoveryMoleculePurine

description

Abstract Electron structures of the fused rings in 7H and 9H tautomers of purine and adenine follow the 4N + 2 rule; the values of pEDA, HOMA, NICS and FLU indices document their aromatic character. In the 1H and 3H tautomers, these rings contain five or seven π electrons, hence they do not follow this rule and consequently exhibit lower aromaticity. This also applies to the aromaticity of whole molecules.

yearjournalcountryeditionlanguage
2019-08-01Tetrahedron
https://doi.org/10.1016/j.tet.2019.130474