Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis

Autores
Zamora, Miguel Angel; Suvire, Fernando Daniel; Enriz, Ricardo Daniel
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The multidimensional conformational potential energy hypersurfaces (PEHSs) for cis-cis-cis 1,4,7 cyclononatriene (I), Tribenzocyclononatriene (TBCN) (II), and cis-cis-cis cyclic triglycine (III) were comprehensively investigated at the Hartree-Fock (HF/6-31G(d)) and density functional theory (B3LYP/6-31G(d,p)) levels of theory. The equilibrium structures, their relative stability, and the transition state (TS) structures involved in the conformational interconversion pathways were analyzed. Altogether, four geometries (two low-energy conformations and two transition states) were found to be important for a description of the conformational features of compounds I-III. B3LYP/aug-cc-pvdz//B31YP/6-31G(d,p) and MP2/6-31G(d,p)//B3LYP/6-31G(d,p) single point calculations predict that the conformational interconversion between crown and twist forms requires 14.01, 26.71, and 17.79 kcal/mol for compounds I, II, and III, respectively, which is in agreement with the available experimental data. A topological study of the conformational PEHSs of compounds I-III was performed. Our results allow us to form a concise idea about the internal intricacies of the PEHSs of compounds I-III, describing the conformations as well as the conformational interconversion process in these hypersurfaces.
Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Suvire, Fernando Daniel. 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
CYCLIC-TRYGLICINE
CYCLONONATRIENE
DFT CALCULATIONS
RING INVERSION
TRIBENZOCYCLONONATRIENE
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:11336/147221
Acceder
id CONICETDig_bcc1297afe210b895fa07bbf035c36e7
oai_identifier_str oai:ri.conicet.gov.ar:11336/147221
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysisZamora, Miguel AngelSuvire, Fernando DanielEnriz, Ricardo DanielAB INITIOCYCLIC-TRYGLICINECYCLONONATRIENEDFT CALCULATIONSRING INVERSIONTRIBENZOCYCLONONATRIENEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The multidimensional conformational potential energy hypersurfaces (PEHSs) for cis-cis-cis 1,4,7 cyclononatriene (I), Tribenzocyclononatriene (TBCN) (II), and cis-cis-cis cyclic triglycine (III) were comprehensively investigated at the Hartree-Fock (HF/6-31G(d)) and density functional theory (B3LYP/6-31G(d,p)) levels of theory. The equilibrium structures, their relative stability, and the transition state (TS) structures involved in the conformational interconversion pathways were analyzed. Altogether, four geometries (two low-energy conformations and two transition states) were found to be important for a description of the conformational features of compounds I-III. B3LYP/aug-cc-pvdz//B31YP/6-31G(d,p) and MP2/6-31G(d,p)//B3LYP/6-31G(d,p) single point calculations predict that the conformational interconversion between crown and twist forms requires 14.01, 26.71, and 17.79 kcal/mol for compounds I, II, and III, respectively, which is in agreement with the available experimental data. A topological study of the conformational PEHSs of compounds I-III was performed. Our results allow us to form a concise idea about the internal intricacies of the PEHSs of compounds I-III, describing the conformations as well as the conformational interconversion process in these hypersurfaces.Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Suvire, Fernando Daniel. 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 Inc2008-01-30info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/147221Zamora, Miguel Angel; Suvire, Fernando Daniel; Enriz, Ricardo Daniel; Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis; John Wiley & Sons Inc; Journal of Computational Chemistry; 29; 2; 30-1-2008; 280-2900192-86511096-987XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/jcc.20789info:eu-repo/semantics/altIdentifier/doi/10.1002/jcc.20789info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:07:28Zoai:ri.conicet.gov.ar:11336/147221instacron: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:34982025-10-15 15:07:28.946CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis
title Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis
spellingShingle Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis
Zamora, Miguel Angel
AB INITIO
CYCLIC-TRYGLICINE
CYCLONONATRIENE
DFT CALCULATIONS
RING INVERSION
TRIBENZOCYCLONONATRIENE
title_short Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis
title_full Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis
title_fullStr Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis
title_full_unstemmed Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis
title_sort Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis
dc.creator.none.fl_str_mv Zamora, Miguel Angel
Suvire, Fernando Daniel
Enriz, Ricardo Daniel
author Zamora, Miguel Angel
author_facet Zamora, Miguel Angel
Suvire, Fernando Daniel
Enriz, Ricardo Daniel
author_role author
author2 Suvire, Fernando Daniel
Enriz, Ricardo Daniel
author2_role author
author
dc.subject.none.fl_str_mv AB INITIO
CYCLIC-TRYGLICINE
CYCLONONATRIENE
DFT CALCULATIONS
RING INVERSION
TRIBENZOCYCLONONATRIENE
topic AB INITIO
CYCLIC-TRYGLICINE
CYCLONONATRIENE
DFT CALCULATIONS
RING INVERSION
TRIBENZOCYCLONONATRIENE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The multidimensional conformational potential energy hypersurfaces (PEHSs) for cis-cis-cis 1,4,7 cyclononatriene (I), Tribenzocyclononatriene (TBCN) (II), and cis-cis-cis cyclic triglycine (III) were comprehensively investigated at the Hartree-Fock (HF/6-31G(d)) and density functional theory (B3LYP/6-31G(d,p)) levels of theory. The equilibrium structures, their relative stability, and the transition state (TS) structures involved in the conformational interconversion pathways were analyzed. Altogether, four geometries (two low-energy conformations and two transition states) were found to be important for a description of the conformational features of compounds I-III. B3LYP/aug-cc-pvdz//B31YP/6-31G(d,p) and MP2/6-31G(d,p)//B3LYP/6-31G(d,p) single point calculations predict that the conformational interconversion between crown and twist forms requires 14.01, 26.71, and 17.79 kcal/mol for compounds I, II, and III, respectively, which is in agreement with the available experimental data. A topological study of the conformational PEHSs of compounds I-III was performed. Our results allow us to form a concise idea about the internal intricacies of the PEHSs of compounds I-III, describing the conformations as well as the conformational interconversion process in these hypersurfaces.
Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Suvire, Fernando Daniel. 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 The multidimensional conformational potential energy hypersurfaces (PEHSs) for cis-cis-cis 1,4,7 cyclononatriene (I), Tribenzocyclononatriene (TBCN) (II), and cis-cis-cis cyclic triglycine (III) were comprehensively investigated at the Hartree-Fock (HF/6-31G(d)) and density functional theory (B3LYP/6-31G(d,p)) levels of theory. The equilibrium structures, their relative stability, and the transition state (TS) structures involved in the conformational interconversion pathways were analyzed. Altogether, four geometries (two low-energy conformations and two transition states) were found to be important for a description of the conformational features of compounds I-III. B3LYP/aug-cc-pvdz//B31YP/6-31G(d,p) and MP2/6-31G(d,p)//B3LYP/6-31G(d,p) single point calculations predict that the conformational interconversion between crown and twist forms requires 14.01, 26.71, and 17.79 kcal/mol for compounds I, II, and III, respectively, which is in agreement with the available experimental data. A topological study of the conformational PEHSs of compounds I-III was performed. Our results allow us to form a concise idea about the internal intricacies of the PEHSs of compounds I-III, describing the conformations as well as the conformational interconversion process in these hypersurfaces.
publishDate 2008
dc.date.none.fl_str_mv 2008-01-30
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/11336/147221
Zamora, Miguel Angel; Suvire, Fernando Daniel; Enriz, Ricardo Daniel; Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis; John Wiley & Sons Inc; Journal of Computational Chemistry; 29; 2; 30-1-2008; 280-290
0192-8651
1096-987X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/147221
identifier_str_mv Zamora, Miguel Angel; Suvire, Fernando Daniel; Enriz, Ricardo Daniel; Ring inversion in 1,4,7 cyclononatriene and analogues: Ab initio and DFT calculations and topological analysis; John Wiley & Sons Inc; Journal of Computational Chemistry; 29; 2; 30-1-2008; 280-290
0192-8651
1096-987X
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/jcc.20789
info:eu-repo/semantics/altIdentifier/doi/10.1002/jcc.20789
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
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
_version_ 1846083219310510080
score 13.22299

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