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

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

1,* , 1
,
1,2
 and
1,2,*
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.
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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