Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102130 |
Resumo: | In this paper we investigated the ability of the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory to predict the 13C nuclear magnetic resonance (NMR) chemical shifts of the 2’-hydroxy-3,4,5-trimethoxy-chalcone molecule. Two different approaches were used. First: the absolute shieldings σ for all carbon atoms in each geometrically optimized conformers of the 2’-hydroxy-3,4,5-trimethoxy-chalcone molecule were calculated at the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory. This approach is further used to generate weighted average values for each atom considering the previously obtained conformational distribution. Second: only the σ for the lowest energetic conformer will be taken to account. The robustness of the method was evaluated for two other chalcones: (E)-1-(4-hydroxy-3-methoxyphenyl)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)prop-2-en-1-one and (E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one, corroborating the ability of the method in chemical shift prevision. Although, both approaches were able to reproduce the chemical shifts of the 2’-hydroxy-3,4,5-trimethoxy-chalcone, significant differences in the calculated values for C-4 and methoxy carbons were observed. The best results were obtained using the second approach (II). |
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Journal of the Brazilian Chemical Society (Online) |
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Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalconechalcone2’-hydroxy-3,4,5-trimethoxy-chalconeGIAO-NMRscaling factorNMR spectroscopyIn this paper we investigated the ability of the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory to predict the 13C nuclear magnetic resonance (NMR) chemical shifts of the 2’-hydroxy-3,4,5-trimethoxy-chalcone molecule. Two different approaches were used. First: the absolute shieldings σ for all carbon atoms in each geometrically optimized conformers of the 2’-hydroxy-3,4,5-trimethoxy-chalcone molecule were calculated at the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory. This approach is further used to generate weighted average values for each atom considering the previously obtained conformational distribution. Second: only the σ for the lowest energetic conformer will be taken to account. The robustness of the method was evaluated for two other chalcones: (E)-1-(4-hydroxy-3-methoxyphenyl)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)prop-2-en-1-one and (E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one, corroborating the ability of the method in chemical shift prevision. Although, both approaches were able to reproduce the chemical shifts of the 2’-hydroxy-3,4,5-trimethoxy-chalcone, significant differences in the calculated values for C-4 and methoxy carbons were observed. The best results were obtained using the second approach (II).Sociedade Brasileira de Química2017-11-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102130Journal of the Brazilian Chemical Society v.28 n.11 2017reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20170060info:eu-repo/semantics/openAccessCosta,Fabio Luiz P.Gomes,Paulo F.Silva,Andressa K.Lião,Luciano M.eng2017-10-26T00:00:00Zoai:scielo:S0103-50532017001102130Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2017-10-26T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone |
title |
Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone |
spellingShingle |
Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone Costa,Fabio Luiz P. chalcone 2’-hydroxy-3,4,5-trimethoxy-chalcone GIAO-NMR scaling factor NMR spectroscopy |
title_short |
Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone |
title_full |
Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone |
title_fullStr |
Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone |
title_full_unstemmed |
Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone |
title_sort |
Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone |
author |
Costa,Fabio Luiz P. |
author_facet |
Costa,Fabio Luiz P. Gomes,Paulo F. Silva,Andressa K. Lião,Luciano M. |
author_role |
author |
author2 |
Gomes,Paulo F. Silva,Andressa K. Lião,Luciano M. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Costa,Fabio Luiz P. Gomes,Paulo F. Silva,Andressa K. Lião,Luciano M. |
dc.subject.por.fl_str_mv |
chalcone 2’-hydroxy-3,4,5-trimethoxy-chalcone GIAO-NMR scaling factor NMR spectroscopy |
topic |
chalcone 2’-hydroxy-3,4,5-trimethoxy-chalcone GIAO-NMR scaling factor NMR spectroscopy |
description |
In this paper we investigated the ability of the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory to predict the 13C nuclear magnetic resonance (NMR) chemical shifts of the 2’-hydroxy-3,4,5-trimethoxy-chalcone molecule. Two different approaches were used. First: the absolute shieldings σ for all carbon atoms in each geometrically optimized conformers of the 2’-hydroxy-3,4,5-trimethoxy-chalcone molecule were calculated at the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory. This approach is further used to generate weighted average values for each atom considering the previously obtained conformational distribution. Second: only the σ for the lowest energetic conformer will be taken to account. The robustness of the method was evaluated for two other chalcones: (E)-1-(4-hydroxy-3-methoxyphenyl)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)prop-2-en-1-one and (E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one, corroborating the ability of the method in chemical shift prevision. Although, both approaches were able to reproduce the chemical shifts of the 2’-hydroxy-3,4,5-trimethoxy-chalcone, significant differences in the calculated values for C-4 and methoxy carbons were observed. The best results were obtained using the second approach (II). |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017-11-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102130 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102130 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20170060 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.28 n.11 2017 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318180017897472 |