NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations

Pierens, Gregory K., Venkatachalam, T. K. and Reutens, David C. (2017) NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations. Scientific Reports, 7 1: 5605.1-5605.9. doi:10.1038/s41598-017-06005-5


Author Pierens, Gregory K.
Venkatachalam, T. K.
Reutens, David C.
Title NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations
Journal name Scientific Reports   Check publisher's open access policy
ISSN 2045-2322
Publication date 2017-12-01
Year available 2017
Sub-type Article (original research)
DOI 10.1038/s41598-017-06005-5
Open Access Status DOI
Volume 7
Issue 1
Start page 5605.1
End page 5605.9
Total pages 9
Place of publication London, United Kingdom
Publisher Nature Publishing Group
Language eng
Subject 1000 General
Abstract A detailed NMR investigation of the chemical shifts of hydrogen and carbon atoms associated with the structure of the naturally occurring alkaloid colchicine was conducted using high field NMR. Initially, the experimental chemical shifts for colchicine in chloroform and DMSO were compared to the values calculated using density functional theory (DFT). There were significant deviations observed for the chloroform solvent, but these were only slight in the DMSO solution. Dilution of the chloroform solution changed the experimental chemical shifts and improved agreement with the DFT calculations, suggesting self-aggregation at higher concentrations. A dimeric model was proposed for which agreement with the DFT calculated chemical shifts was better than for corresponding monomeric structures. Three further solvents were studied to evaluate changes in chemical shift values at different dilutions. Chloroform, benzene and water showed significant chemical shift changes implying self-aggregation, whereas DMSO and acetone did not show significant change upon dilution.
Keyword Nuclear magnetic resonance (NMR)
Density functional theory (DFT)
Colchicine
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
Centre for Advanced Imaging Publications
 
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