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Rationalizing the Structural Variability of the Exocyclic Amino Groups in Nucleobases and Their Metal Complexes: Cytosine and Adenine

2014; Wiley; Volume: 20; Issue: 31 Linguagem: Inglês

10.1002/chem.201403066

1521-3765

Célia Fonseca Guerra, Pablo J. Sanz Miguel, Andrea Cebollada, F. Matthias Bickelhaupt, Bernhard Lippert,

RNA and protein synthesis mechanisms

Abstract The exocyclic amino groups of cytosine and adenine nucleobases are normally almost flat, with the N atoms essentially sp 2 hybridized and the lone pair largely delocalized into the heterocyclic rings. However, a change to marked pyramidality of the amino group (N then sp 3 hybridized, lone pair essentially localized at N) occurs during i) involvement of an amino proton in strong hydrogen bonding donor conditions or ii) with monofunctional metal coordination following removal of one of the two protons.