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Symmetry 2014, 6(2), 345-367; doi:10.3390/sym6020345

Dynamic Processes in Prochiral Solvating Agents (pro-CSAs) Studied by NMR Spectroscopy

1
World Premier International (WPI) Research Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan
2
Core Research for Evolutionary Science and Technology (CREST), Japan Science and Technology Agency (JST), Gobancho, Chiyoda-ku, Tokyo 102-0076, Japan
*
Authors to whom correspondence should be addressed.
Received: 12 March 2014 / Revised: 7 May 2014 / Accepted: 7 May 2014 / Published: 14 May 2014
(This article belongs to the Special Issue Supramolecular Chirality)
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Abstract

Several dynamic processes, including tautomerism and macrocyclic inversion, in 1H-NMR prochiral solvating agents (pro-CSAs) are investigated. Various features of pro-CSA, including modes of interaction for complex formation, stoichiometry, binding strength and temperature effects were compared for three representative pro-CSA molecules. Structural effects of conjugated tetrapyrrole pro-CSA on the mechanism of enantiomeric excess determination are also discussed. Detailed analysis of species (complexes) and dynamic processes occurring in solution and their 1H-NMR spectral manifestations at various temperatures is presented. View Full-Text
Keywords: prochiral solvating agent; pro-CSA; host–guest complexation; charge transfer complex; hydrogen bond; enantiomeric excess; chirality; 1H-NMR; tetrapyrrole prochiral solvating agent; pro-CSA; host–guest complexation; charge transfer complex; hydrogen bond; enantiomeric excess; chirality; 1H-NMR; tetrapyrrole
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Labuta, J.; Ishihara, S.; Ariga, K.; Hill, J.P. Dynamic Processes in Prochiral Solvating Agents (pro-CSAs) Studied by NMR Spectroscopy. Symmetry 2014, 6, 345-367.

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