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

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 t...

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Autores principales:	Gregory K. Pierens, T. K. Venkatachalam, David C. Reutens
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/d857b1422a124fbba8eb18831bde812e
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spelling	oai:doaj.org-article:d857b1422a124fbba8eb18831bde812e2021-12-02T11:52:26ZNMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations10.1038/s41598-017-06005-52045-2322https://doaj.org/article/d857b1422a124fbba8eb18831bde812e2017-07-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-06005-5https://doaj.org/toc/2045-2322Abstract 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.Gregory K. PierensT. K. VenkatachalamDavid C. ReutensNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-9 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Gregory K. Pierens T. K. Venkatachalam David C. Reutens NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations
description	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.
format	article
author	Gregory K. Pierens T. K. Venkatachalam David C. Reutens
author_facet	Gregory K. Pierens T. K. Venkatachalam David C. Reutens
author_sort	Gregory K. Pierens
title	NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations
title_short	NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations
title_full	NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations
title_fullStr	NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations
title_full_unstemmed	NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations
title_sort	nmr and dft investigations of structure of colchicine in various solvents including density functional theory calculations
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/d857b1422a124fbba8eb18831bde812e
work_keys_str_mv	AT gregorykpierens nmranddftinvestigationsofstructureofcolchicineinvarioussolventsincludingdensityfunctionaltheorycalculations AT tkvenkatachalam nmranddftinvestigationsofstructureofcolchicineinvarioussolventsincludingdensityfunctionaltheorycalculations AT davidcreutens nmranddftinvestigationsofstructureofcolchicineinvarioussolventsincludingdensityfunctionaltheorycalculations
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NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations

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