Rationalizing the Structural Variability of the Exocyclic Amino Groups in Nucleobases and Their Metal Complexes: Cytosine and Adenine |
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| Authors: | Dr. Célia Fonseca Guerra Dr. Pablo J. Sanz Miguel Andrea Cebollada Prof. Dr. F. Matthias Bickelhaupt Prof. Dr. Bernhard Lippert |
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| Affiliation: | 1. Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling (ACMM), VU University Amsterdam, 1081 HV Amsterdam (The Netherlands);2. Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza‐CSIC, 50009 Zaragoza (Spain);3. Institute for Molecules and Materials (IMM), Radboud University Nijmegen, 6525 AJ Nijmegen (The Netherlands);4. Fakult?t Chemie und Chemische Biologie (CCB), Technische Universit?t Dortmund, 44221 Dortmund (Germany) |
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| Abstract: | ![]()
The exocyclic amino groups of cytosine and adenine nucleobases are normally almost flat, with the N atoms essentially sp2 hybridized and the lone pair largely delocalized into the heterocyclic rings. However, a change to marked pyramidality of the amino group (N then sp3 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. |
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| Keywords: | cytosine DFT calculations hybridization state metal coordination nucleobase amino groups |
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