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  Structural and chiroptical analysis of naturally occurring (-)-strychnine.

Reinscheid, F., Schmidt, M., Abromeit, H., Liening, S., Scriba, G. K. E., & Reinscheid, U. M. (2016). Structural and chiroptical analysis of naturally occurring (-)-strychnine. Journal of Molecular Structure, 1106, 200-209. doi:10.1016/j.molstruc.2015.10.062.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0029-5AB6-3 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002E-0E83-D
Genre: Journal Article

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 Creators:
Reinscheid, F.1, Author              
Schmidt, M.1, Author              
Abromeit, H., Author
Liening, S., Author
Scriba, G. K. E., Author
Reinscheid, U. M.1, Author              
Affiliations:
1Department of NMR Based Structural Biology, MPI for Biophysical Chemistry, Max Planck Society, ou_578567              

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Free keywords: Strychnine; Structure; NMR; Optical rotation; Electronic circular dichroism; Conformation
 Abstract: Structural aspects such as chemical exchange, dimerization, solvent association, nitrogen inversion and protonation status of strychnine were investigated using experimental and calculated data. The information was mainly interpreted in view of a successful determination of the absolute configuration (AC) with strychnine (base and salt) as test molecule due to its importance in chemistry. By geometry optimization a stable isomer of protonated strychnine was found with an inverted nitrogen, however, 25 kcal/mol higher in energy. It is shown that solvent association can be assumed in protic solvents such as methanol and dimerization to a small extent in polar/protic solvents. However, the monomeric structural model neglecting explicit solvent molecules still allows the correct prediction of the AC of base and hydrochloride using optical rotation and ECD data.

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Language(s): eng - English
 Dates: 2015-10-232016-02-15
 Publication Status: Published in print
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 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1016/j.molstruc.2015.10.062
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Title: Journal of Molecular Structure
Source Genre: Journal
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Pages: - Volume / Issue: 1106 Sequence Number: - Start / End Page: 200 - 209 Identifier: -