Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study

Autores
Zamora, Miguel Angel; Masman, Marcelo Fabricio; Bombasaro, José Abel; Freile, Monica Liliana; Filho, Valdir Cechinel; López, Silvia Noelí; Zacchino, Susana Alicia Stella; Enriz, Ricardo Daniel
Año de publicación
2003
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A conformational and electronic study on N-phenylalkyl-3,4-dichloromaleimides, a new series of antifungal compounds, was carried out. In this study ab initio [RHF/3-21G and RHF/6-31G(d)] and density functional theory (B3LYP/6-31G(d)) calculations were performed. The effect of solvent (water) was taken into account by performing calculations with the isodensity polarizable continuum model method. The electronic study of the compounds was carried out using molecular electrostatic potentials. The presence of two symmetrical aromatic systems reduces notably the conformational possibilities of these maleimides. The results permit the recognition of the minimal structural requirements for the production of the antifungal response; a 3,4-dichloroimido ring and a benzene ring appear to be indispensable. Also, theoretical calculations suggest that the optimum interatomic distance between these moieties is about 3.5-5.0 Å.
Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Masman, Marcelo Fabricio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Área Química General e Inorgánica; Argentina
Fil: Bombasaro, José Abel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Freile, Monica Liliana. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina
Fil: Filho, Valdir Cechinel. Universidade do Vale do Itajaí; Brasil
Fil: López, Silvia Noelí. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Materia
AB INITIO AND DFT CALCULATIONS
ANTIFUNGAL ACTIVITY
CONFORMATIONAL STUDY
MALEIMIDES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/136111
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/136111
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT studyZamora, Miguel AngelMasman, Marcelo FabricioBombasaro, José AbelFreile, Monica LilianaFilho, Valdir CechinelLópez, Silvia NoelíZacchino, Susana Alicia StellaEnriz, Ricardo DanielAB INITIO AND DFT CALCULATIONSANTIFUNGAL ACTIVITYCONFORMATIONAL STUDYMALEIMIDEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A conformational and electronic study on N-phenylalkyl-3,4-dichloromaleimides, a new series of antifungal compounds, was carried out. In this study ab initio [RHF/3-21G and RHF/6-31G(d)] and density functional theory (B3LYP/6-31G(d)) calculations were performed. The effect of solvent (water) was taken into account by performing calculations with the isodensity polarizable continuum model method. The electronic study of the compounds was carried out using molecular electrostatic potentials. The presence of two symmetrical aromatic systems reduces notably the conformational possibilities of these maleimides. The results permit the recognition of the minimal structural requirements for the production of the antifungal response; a 3,4-dichloroimido ring and a benzene ring appear to be indispensable. Also, theoretical calculations suggest that the optimum interatomic distance between these moieties is about 3.5-5.0 Å.Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Masman, Marcelo Fabricio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Área Química General e Inorgánica; ArgentinaFil: Bombasaro, José Abel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Freile, Monica Liliana. Universidad Nacional de la Patagonia "San Juan Bosco"; ArgentinaFil: Filho, Valdir Cechinel. Universidade do Vale do Itajaí; BrasilFil: López, Silvia Noelí. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaJohn Wiley & Sons Inc2003-02-19info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/136111Zamora, Miguel Angel; Masman, Marcelo Fabricio; Bombasaro, José Abel; Freile, Monica Liliana; Filho, Valdir Cechinel; et al.; Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study; John Wiley & Sons Inc; International Journal of Quantum Chemistry; 93; 1; 19-2-2003; 32-460020-76081097-461XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/qua.10524info:eu-repo/semantics/altIdentifier/doi/10.1002/qua.10524info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:49:21Zoai:ri.conicet.gov.ar:11336/136111instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:49:21.523CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study
title Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study
spellingShingle Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study
Zamora, Miguel Angel
AB INITIO AND DFT CALCULATIONS
ANTIFUNGAL ACTIVITY
CONFORMATIONAL STUDY
MALEIMIDES
title_short Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study
title_full Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study
title_fullStr Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study
title_full_unstemmed Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study
title_sort Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study
dc.creator.none.fl_str_mv Zamora, Miguel Angel
Masman, Marcelo Fabricio
Bombasaro, José Abel
Freile, Monica Liliana
Filho, Valdir Cechinel
López, Silvia Noelí
Zacchino, Susana Alicia Stella
Enriz, Ricardo Daniel
author Zamora, Miguel Angel
author_facet Zamora, Miguel Angel
Masman, Marcelo Fabricio
Bombasaro, José Abel
Freile, Monica Liliana
Filho, Valdir Cechinel
López, Silvia Noelí
Zacchino, Susana Alicia Stella
Enriz, Ricardo Daniel
author_role author
author2 Masman, Marcelo Fabricio
Bombasaro, José Abel
Freile, Monica Liliana
Filho, Valdir Cechinel
López, Silvia Noelí
Zacchino, Susana Alicia Stella
Enriz, Ricardo Daniel
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv AB INITIO AND DFT CALCULATIONS
ANTIFUNGAL ACTIVITY
CONFORMATIONAL STUDY
MALEIMIDES
topic AB INITIO AND DFT CALCULATIONS
ANTIFUNGAL ACTIVITY
CONFORMATIONAL STUDY
MALEIMIDES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A conformational and electronic study on N-phenylalkyl-3,4-dichloromaleimides, a new series of antifungal compounds, was carried out. In this study ab initio [RHF/3-21G and RHF/6-31G(d)] and density functional theory (B3LYP/6-31G(d)) calculations were performed. The effect of solvent (water) was taken into account by performing calculations with the isodensity polarizable continuum model method. The electronic study of the compounds was carried out using molecular electrostatic potentials. The presence of two symmetrical aromatic systems reduces notably the conformational possibilities of these maleimides. The results permit the recognition of the minimal structural requirements for the production of the antifungal response; a 3,4-dichloroimido ring and a benzene ring appear to be indispensable. Also, theoretical calculations suggest that the optimum interatomic distance between these moieties is about 3.5-5.0 Å.
Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Masman, Marcelo Fabricio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Área Química General e Inorgánica; Argentina
Fil: Bombasaro, José Abel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Freile, Monica Liliana. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina
Fil: Filho, Valdir Cechinel. Universidade do Vale do Itajaí; Brasil
Fil: López, Silvia Noelí. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
description A conformational and electronic study on N-phenylalkyl-3,4-dichloromaleimides, a new series of antifungal compounds, was carried out. In this study ab initio [RHF/3-21G and RHF/6-31G(d)] and density functional theory (B3LYP/6-31G(d)) calculations were performed. The effect of solvent (water) was taken into account by performing calculations with the isodensity polarizable continuum model method. The electronic study of the compounds was carried out using molecular electrostatic potentials. The presence of two symmetrical aromatic systems reduces notably the conformational possibilities of these maleimides. The results permit the recognition of the minimal structural requirements for the production of the antifungal response; a 3,4-dichloroimido ring and a benzene ring appear to be indispensable. Also, theoretical calculations suggest that the optimum interatomic distance between these moieties is about 3.5-5.0 Å.
publishDate 2003
dc.date.none.fl_str_mv 2003-02-19
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/136111
Zamora, Miguel Angel; Masman, Marcelo Fabricio; Bombasaro, José Abel; Freile, Monica Liliana; Filho, Valdir Cechinel; et al.; Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study; John Wiley & Sons Inc; International Journal of Quantum Chemistry; 93; 1; 19-2-2003; 32-46
0020-7608
1097-461X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/136111
identifier_str_mv Zamora, Miguel Angel; Masman, Marcelo Fabricio; Bombasaro, José Abel; Freile, Monica Liliana; Filho, Valdir Cechinel; et al.; Conformational and electronic study of N-phenylalkyl-3,4-dichloromaleimides: Ab initio and DFT study; John Wiley & Sons Inc; International Journal of Quantum Chemistry; 93; 1; 19-2-2003; 32-46
0020-7608
1097-461X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/qua.10524
info:eu-repo/semantics/altIdentifier/doi/10.1002/qua.10524
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons Inc
publisher.none.fl_str_mv John Wiley & Sons Inc
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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