Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol
The structural determination of small organic molecules is mainly undertaken by using NMR techniques, although it is increasingly supplemented by using computational methods. NMR parameters, such as chemical shifts and coupling constants, are extremely sensitive indicators of local molecular conformation and are a source of structural evidence. However, their interpretation is fairly challenging in many circumstances, such as the case of the new polyether squalene derivative nivariol, the structure of which was elucidated by means of NMR spectroscopy and DFT calculations. The potential flexibility of this molecule and the high number of quaternary carbon atoms that it contains make its configurational assignment very difficult. Moreover, the relative configuration of four separated stereoclusters was established and subsequently connected by using NOE and J ‐based analysis, as well as by a comparison of its experimental 13C NMR chemical shifts with the corresponding population‐weighted values, as calculated by using DFT methods. Limitations of these used approaches became apparent but were overcome by combining the two methods.
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Wiley-VCH
2013-06-24
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Subjects: | Cluster compounds, Conformational analysis, Density functional calculations, NMR spectroscopy, Natural products, |
Online Access: | http://hdl.handle.net/10261/213248 |
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dig-ipna-es-10261-2132482020-06-04T08:06:10Z Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol Cen‐Pacheco, Francisco Rodríguez, Jaime Norte, Manuel Fernández, José J. Hernández Daranas, Antonio Centro de Supercomputación de Galicia Cluster compounds Conformational analysis Density functional calculations NMR spectroscopy Natural products The structural determination of small organic molecules is mainly undertaken by using NMR techniques, although it is increasingly supplemented by using computational methods. NMR parameters, such as chemical shifts and coupling constants, are extremely sensitive indicators of local molecular conformation and are a source of structural evidence. However, their interpretation is fairly challenging in many circumstances, such as the case of the new polyether squalene derivative nivariol, the structure of which was elucidated by means of NMR spectroscopy and DFT calculations. The potential flexibility of this molecule and the high number of quaternary carbon atoms that it contains make its configurational assignment very difficult. Moreover, the relative configuration of four separated stereoclusters was established and subsequently connected by using NOE and J ‐based analysis, as well as by a comparison of its experimental 13C NMR chemical shifts with the corresponding population‐weighted values, as calculated by using DFT methods. Limitations of these used approaches became apparent but were overcome by combining the two methods. Peer reviewed 2020-06-03T14:58:51Z 2020-06-03T14:58:51Z 2013-06-24 artículo http://purl.org/coar/resource_type/c_6501 Chemistry - a European Journal 19(26): 8525-8532 (2013) 0947-6539 http://hdl.handle.net/10261/213248 10.1002/chem.201204272 1521-3765 en Postprint https://doi.org/10.1002/chem.201204272 No none Wiley-VCH |
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Cluster compounds Conformational analysis Density functional calculations NMR spectroscopy Natural products Cluster compounds Conformational analysis Density functional calculations NMR spectroscopy Natural products Cen‐Pacheco, Francisco Rodríguez, Jaime Norte, Manuel Fernández, José J. Hernández Daranas, Antonio Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol |
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The structural determination of small organic molecules is mainly undertaken by using NMR techniques, although it is increasingly supplemented by using computational methods. NMR parameters, such as chemical shifts and coupling constants, are extremely sensitive indicators of local molecular conformation and are a source of structural evidence. However, their interpretation is fairly challenging in many circumstances, such as the case of the new polyether squalene derivative nivariol, the structure of which was elucidated by means of NMR spectroscopy and DFT calculations. The potential flexibility of this molecule and the high number of quaternary carbon atoms that it contains make its configurational assignment very difficult. Moreover, the relative configuration of four separated stereoclusters was established and subsequently connected by using NOE and J ‐based analysis, as well as by a comparison of its experimental 13C NMR chemical shifts with the corresponding population‐weighted values, as calculated by using DFT methods. Limitations of these used approaches became apparent but were overcome by combining the two methods. |
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Centro de Supercomputación de Galicia |
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Centro de Supercomputación de Galicia Cen‐Pacheco, Francisco Rodríguez, Jaime Norte, Manuel Fernández, José J. Hernández Daranas, Antonio |
format |
artículo |
topic_facet |
Cluster compounds Conformational analysis Density functional calculations NMR spectroscopy Natural products |
author |
Cen‐Pacheco, Francisco Rodríguez, Jaime Norte, Manuel Fernández, José J. Hernández Daranas, Antonio |
author_sort |
Cen‐Pacheco, Francisco |
title |
Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol |
title_short |
Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol |
title_full |
Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol |
title_fullStr |
Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol |
title_full_unstemmed |
Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol |
title_sort |
connecting discrete stereoclusters by using dft and nmr spectroscopy: the case of nivariol |
publisher |
Wiley-VCH |
publishDate |
2013-06-24 |
url |
http://hdl.handle.net/10261/213248 |
work_keys_str_mv |
AT cenpachecofrancisco connectingdiscretestereoclustersbyusingdftandnmrspectroscopythecaseofnivariol AT rodriguezjaime connectingdiscretestereoclustersbyusingdftandnmrspectroscopythecaseofnivariol AT nortemanuel connectingdiscretestereoclustersbyusingdftandnmrspectroscopythecaseofnivariol AT fernandezjosej connectingdiscretestereoclustersbyusingdftandnmrspectroscopythecaseofnivariol AT hernandezdaranasantonio connectingdiscretestereoclustersbyusingdftandnmrspectroscopythecaseofnivariol |
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1777669857772306432 |