The effects of interactions between proline and carbon nanostructures on organocatalysis in the Hajos–Parrish–Eder–Sauer–Wiechert reaction
作者： G. A. Rance , A. N. Khlobystov
DOI: 10.1039/C4NR04009K
关键词: Organocatalysis 、 Fullerene 、 Photochemistry 、 Lone pair 、 Aldol reaction 、 Hajos–Parrish–Eder–Sauer–Wiechert reaction 、 Nucleophile 、 Catalysis 、 Selectivity 、 Chemistry
摘要: The non-covalent interactions of S-(-)-proline with the surfaces carbon nanostructures (fullerene, nanotubes and graphite) change nucleophilic-electrophilic acid-base properties amino acid, thus tuning its activity selectivity in organocatalytic Hajos-Parrish-Eder-Sauer-Wiechert (HPESW) reaction. Whilst our spectroscopy microscopy measurements show no permanent covalent bonding between nanostructures, a systematic investigation catalytic organocatalyst HPESW reaction demonstrates clear correlation pyramidalisation angle S-(-)-proline. Carbon larger angles have stronger interaction nitrogen atom lone pair electrons organocatalyst, thereby simultaneously decreasing nucleophilicity increasing acidity organocatalyst. These translate into lower conversion rates but higher selectivities towards dehydrated product Aldol addition.
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