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- Publisher
- Springer Journals
- Copyright
- Copyright © 2010 by Akadémiai Kiadó, Budapest, Hungary
- Subject
- Chemistry; Inorganic Chemistry ; Diagnostic Radiology; Nuclear Physics, Heavy Ions, Hadrons; Physical Chemistry ; Nuclear Chemistry
- ISSN
- 0236-5731
- eISSN
- 1588-2780
- DOI
- 10.1007/s10967-010-0823-y
- Publisher site
- See Article on Publisher Site
Abstract
Chiral Ni(II) complexes are used for the preparation of carbon-11 or fluorine-18 enantiomerically pure α-amino acids for positron emission tomography (PET). They enable the selective monoalkylation of a glycine synthon with high stereoselectivity and the preparation of enantiomerically pure α-amino acids with quarternary α-carbon. Molecular modelling of non-, mono- and di-substituted complexes using quantum theory of atoms-in-molecule (QTAIM) topological analysis of electron density allowed us to formulate a new theory explaining the reasons for highly selective monomethylation of the complexes. In the non-substituted complex (GK), the α-carbon atom exhibits a higher atomic volume and a more positive charge in comparison with mono- and di-substituted complexes. This unusual behaviour is accompanied by increasing the bond critical point (BCP) ellipticity of the iminic bond in GK explained by the higher mechanical strain. Both phenomena indicate the increased reactivity and probably originate in more compact core of GK where shorter distances in the internal coordination sphere result in the higher strain of its bonds.
Journal
Journal of Radioanalytical and Nuclear Chemistry – Springer Journals
Published: Dec 1, 2010