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The effects of interactions between proline and carbon nanostructures on organocatalysis in the Hajos-Parrish-Eder-Sauer-Wiechert reaction

Rance, G.A.; Khlobystov, Andrei N.

Authors

G.A. Rance

Andrei N. Khlobystov



Abstract

The non-covalent interactions of S-(-)-proline with the surfaces of carbon nanostructures (fullerene, nanotubes and graphite) change the nucleophilic-electrophilic and acid-base properties of the amino acid, thus tuning its activity and selectivity in the organocatalytic Hajos-Parrish-Eder-Sauer-Wiechert (HPESW) reaction. Whilst our spectroscopy and microscopy measurements show no permanent covalent bonding between S-(-)-proline and carbon nanostructures, a systematic investigation of the catalytic activity and selectivity of the organocatalyst in the HPESW reaction demonstrates a clear correlation between the pyramidalisation angle of carbon nanostructures and the catalytic properties of S-(-)-proline. Carbon nanostructures with larger pyramidalisation angles have a stronger interaction with the nitrogen atom lone pair of electrons of the organocatalyst, thereby simultaneously decreasing the nucleophilicity and increasing the acidity of the organocatalyst. These translate into lower conversion rates but higher selectivities towards the dehydrated product of Aldol addition.

Citation

Rance, G., & Khlobystov, A. N. (in press). The effects of interactions between proline and carbon nanostructures on organocatalysis in the Hajos-Parrish-Eder-Sauer-Wiechert reaction. Nanoscale, 6, https://doi.org/10.1039/C4NR04009K

Journal Article Type Article
Acceptance Date Jul 24, 2014
Online Publication Date Jul 25, 2014
Deposit Date Oct 4, 2017
Publicly Available Date Oct 4, 2017
Journal Nanoscale
Print ISSN 2040-3364
Electronic ISSN 2040-3372
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 6
DOI https://doi.org/10.1039/C4NR04009K
Public URL http://eprints.nottingham.ac.uk/id/eprint/46853
Publisher URL http://pubs.rsc.org/en/content/articlehtml/2014/nr/c4nr04009k
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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