Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction

Detalhes bibliográficos
Autor(a) principal: Silva, Daniela Rodrigues
Data de Publicação: 2020
Outros Autores: Daré, Joyce K., Freitas, Matheus P.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFLA
Texto Completo: http://repositorio.ufla.br/jspui/handle/1/48540
Resumo: Molecular polarity governs lipophilicity, which in turn determines important agrochemical and environmental properties, such as soil sorption and bioconcentration of organic compounds. Since the C–F bond is the most polar in organic chemistry, the orientation of fluorine substituents originating from the rotation around C–C(F) bonds should affect the polarity and, consequently, the physicochemical and biological properties of fluorine-containing agrochemicals. Accordingly, this study aims to determine the most likely conformers of some fluorine-containing agrochemicals and to correlate their molecular dipole moments with the respective n-octanol/water partition coefficients (log P), in order to investigate the dependence of the lipophilicity with the molecular conformation.
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spelling Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity predictionDipole momentFluorinated compoundsGauche effectHerbicidesLog PDefensivos agrícolasMomento dipolarCompostos fluoradosEfeito GaucheHerbicidasMolecular polarity governs lipophilicity, which in turn determines important agrochemical and environmental properties, such as soil sorption and bioconcentration of organic compounds. Since the C–F bond is the most polar in organic chemistry, the orientation of fluorine substituents originating from the rotation around C–C(F) bonds should affect the polarity and, consequently, the physicochemical and biological properties of fluorine-containing agrochemicals. Accordingly, this study aims to determine the most likely conformers of some fluorine-containing agrochemicals and to correlate their molecular dipole moments with the respective n-octanol/water partition coefficients (log P), in order to investigate the dependence of the lipophilicity with the molecular conformation.Beilstein-Institut2021-11-24T17:44:12Z2021-11-24T17:44:12Z2020-10info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfSILVA, D. R.; DARÉ, J. K.; FREITAS, M. P. Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction. Beilstein Journal of Organic Chemistry, Frankfurt am Main, v. 16, p. 2469-2476, 2020. DOI: https://doi.org/10.3762/bjoc.16.200.http://repositorio.ufla.br/jspui/handle/1/48540Beilstein Journal of Organic Chemistryreponame:Repositório Institucional da UFLAinstname:Universidade Federal de Lavras (UFLA)instacron:UFLAhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessSilva, Daniela RodriguesDaré, Joyce K.Freitas, Matheus P.eng2021-11-24T17:44:37Zoai:localhost:1/48540Repositório InstitucionalPUBhttp://repositorio.ufla.br/oai/requestnivaldo@ufla.br || repositorio.biblioteca@ufla.bropendoar:2021-11-24T17:44:37Repositório Institucional da UFLA - Universidade Federal de Lavras (UFLA)false
dc.title.none.fl_str_mv Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
title Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
spellingShingle Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
Silva, Daniela Rodrigues
Dipole moment
Fluorinated compounds
Gauche effect
Herbicides
Log P
Defensivos agrícolas
Momento dipolar
Compostos fluorados
Efeito Gauche
Herbicidas
title_short Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
title_full Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
title_fullStr Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
title_full_unstemmed Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
title_sort Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
author Silva, Daniela Rodrigues
author_facet Silva, Daniela Rodrigues
Daré, Joyce K.
Freitas, Matheus P.
author_role author
author2 Daré, Joyce K.
Freitas, Matheus P.
author2_role author
author
dc.contributor.author.fl_str_mv Silva, Daniela Rodrigues
Daré, Joyce K.
Freitas, Matheus P.
dc.subject.por.fl_str_mv Dipole moment
Fluorinated compounds
Gauche effect
Herbicides
Log P
Defensivos agrícolas
Momento dipolar
Compostos fluorados
Efeito Gauche
Herbicidas
topic Dipole moment
Fluorinated compounds
Gauche effect
Herbicides
Log P
Defensivos agrícolas
Momento dipolar
Compostos fluorados
Efeito Gauche
Herbicidas
description Molecular polarity governs lipophilicity, which in turn determines important agrochemical and environmental properties, such as soil sorption and bioconcentration of organic compounds. Since the C–F bond is the most polar in organic chemistry, the orientation of fluorine substituents originating from the rotation around C–C(F) bonds should affect the polarity and, consequently, the physicochemical and biological properties of fluorine-containing agrochemicals. Accordingly, this study aims to determine the most likely conformers of some fluorine-containing agrochemicals and to correlate their molecular dipole moments with the respective n-octanol/water partition coefficients (log P), in order to investigate the dependence of the lipophilicity with the molecular conformation.
publishDate 2020
dc.date.none.fl_str_mv 2020-10
2021-11-24T17:44:12Z
2021-11-24T17:44:12Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv SILVA, D. R.; DARÉ, J. K.; FREITAS, M. P. Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction. Beilstein Journal of Organic Chemistry, Frankfurt am Main, v. 16, p. 2469-2476, 2020. DOI: https://doi.org/10.3762/bjoc.16.200.
http://repositorio.ufla.br/jspui/handle/1/48540
identifier_str_mv SILVA, D. R.; DARÉ, J. K.; FREITAS, M. P. Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction. Beilstein Journal of Organic Chemistry, Frankfurt am Main, v. 16, p. 2469-2476, 2020. DOI: https://doi.org/10.3762/bjoc.16.200.
url http://repositorio.ufla.br/jspui/handle/1/48540
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Beilstein-Institut
publisher.none.fl_str_mv Beilstein-Institut
dc.source.none.fl_str_mv Beilstein Journal of Organic Chemistry
reponame:Repositório Institucional da UFLA
instname:Universidade Federal de Lavras (UFLA)
instacron:UFLA
instname_str Universidade Federal de Lavras (UFLA)
instacron_str UFLA
institution UFLA
reponame_str Repositório Institucional da UFLA
collection Repositório Institucional da UFLA
repository.name.fl_str_mv Repositório Institucional da UFLA - Universidade Federal de Lavras (UFLA)
repository.mail.fl_str_mv nivaldo@ufla.br || repositorio.biblioteca@ufla.br
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