Electronic structure of the enolate anion of chlorophyll b |
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| Authors: | Paavo H Hynninen Jari S Kavakka |
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| Institution: | a Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, A.I. Virtasen Aukio 1, PO Box 55, FIN-00014 Helsinki, Finland
b Finnish Institute for Verification of the Chemical Weapons Convention (VERIFIN), University of Helsinki, A.I. Virtasen Aukio 1, PO Box 55, FIN-00014 Helsinki, Finland |
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| Abstract: | The enolate anion of chlorophyll b (Chl b) has been synthesized under deoxygenated conditions and its electronic structure characterized for the first time by 1H NMR and electronic absorption spectroscopy. The formation of the enolate anion caused a marked perturbation to the 18 π-electron 18]diazaannulene aromatic pathway of Chl b. This perturbation appeared as noticeable upfield shifts, exceeding 1 ppm, for the meso-CH protons of the Chl b enolate anion. Nevertheless, the enolate anion remained diatropic, maintaining aromaticity in its delocalized macrocycle. |
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| Keywords: | Electron delocalization Aromaticity Chlorophyll enolization Photosynthesis NMR Spectroscopy |
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