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Rationalizing the Structural Variability of the Exocyclic Amino Groups in Nucleobases and Their Metal Complexes: Cytosine and Adenine
Author(s) -
Fonseca Guerra Célia,
Sanz Miguel Pablo J.,
Cebollada Andrea,
Bickelhaupt F. Matthias,
Lippert Bernhard
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403066
Subject(s) - nucleobase , cytosine , lone pair , delocalized electron , chemistry , hydrogen bond , stereochemistry , metal , amino acid , guanine , crystallography , dna , molecule , biochemistry , organic chemistry , nucleotide , gene
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.