Stereoelectronic interactions and molecular properties: An NBO-based study of uracil
- Autores
- Sproviero, Eduardo M.; Burton, Gerardo
- Año de publicación
- 2003
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- The contributions of stereoelectronic interactions to several molecular properties are used to analyze the propagation of information between different parts of the uracil molecule with a method that is based on the natural bond orbital (NBO) deletion technique. The emphasis is not on the effect of the contributions of localized orbitals to selected properties but rather on their interactions, giving information that is complementary to that resulting from a standard localized molecular orbital contribution. The analysis of how information between orbitals is transmitted throughout the molecule allows interpretation of the ways in which an interaction can affect a molecular property localized in the same region or in a different region of the molecule. A network of stereoelectronic interactions was identified in the uracil molecule, and the relative influences of the interactions that transmit information between different parts of the molecule were evaluated. An analysis was performed over localized properties on atoms and bonds of the two carbonyl groups, namely bond orders, distribution of electronic charge, and NMR shielding tensors. Interactions n(N3) → π*(C4=O) and n(N1) → π*(C5=C6) were the most important delocalizations that carry information concerning the change of substituents at C-5, whereas interactions n(N1) → π*(C2=O) and n(N3) rarr; π*(C2=O) were those mainly responsible for transmitting this information to the C-2 uracil carbonyl (C2=O) properties.
Fil: Sproviero, Eduardo M.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Burton, Gerardo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina - Materia
- NBO
- Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/88190
Ver los metadatos del registro completo
id |
CONICETDig_d03b383778a4b7b604e0bb3490e3d0ad |
---|---|
oai_identifier_str |
oai:ri.conicet.gov.ar:11336/88190 |
network_acronym_str |
CONICETDig |
repository_id_str |
3498 |
network_name_str |
CONICET Digital (CONICET) |
spelling |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracilSproviero, Eduardo M.Burton, GerardoNBOhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The contributions of stereoelectronic interactions to several molecular properties are used to analyze the propagation of information between different parts of the uracil molecule with a method that is based on the natural bond orbital (NBO) deletion technique. The emphasis is not on the effect of the contributions of localized orbitals to selected properties but rather on their interactions, giving information that is complementary to that resulting from a standard localized molecular orbital contribution. The analysis of how information between orbitals is transmitted throughout the molecule allows interpretation of the ways in which an interaction can affect a molecular property localized in the same region or in a different region of the molecule. A network of stereoelectronic interactions was identified in the uracil molecule, and the relative influences of the interactions that transmit information between different parts of the molecule were evaluated. An analysis was performed over localized properties on atoms and bonds of the two carbonyl groups, namely bond orders, distribution of electronic charge, and NMR shielding tensors. Interactions n(N3) → π*(C4=O) and n(N1) → π*(C5=C6) were the most important delocalizations that carry information concerning the change of substituents at C-5, whereas interactions n(N1) → π*(C2=O) and n(N3) rarr; π*(C2=O) were those mainly responsible for transmitting this information to the C-2 uracil carbonyl (C2=O) properties.Fil: Sproviero, Eduardo M.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Burton, Gerardo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaAmerican Chemical Society2003-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/88190Sproviero, Eduardo M.; Burton, Gerardo; Stereoelectronic interactions and molecular properties: An NBO-based study of uracil; American Chemical Society; Journal of Physical Chemistry A; 107; 29; 7-2003; 5544-55541089-5639CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jp0271763info:eu-repo/semantics/altIdentifier/doi/10.1021/jp0271763info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:43:20Zoai:ri.conicet.gov.ar:11336/88190instacron: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:34982025-09-29 09:43:20.298CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracil |
title |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracil |
spellingShingle |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracil Sproviero, Eduardo M. NBO |
title_short |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracil |
title_full |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracil |
title_fullStr |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracil |
title_full_unstemmed |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracil |
title_sort |
Stereoelectronic interactions and molecular properties: An NBO-based study of uracil |
dc.creator.none.fl_str_mv |
Sproviero, Eduardo M. Burton, Gerardo |
author |
Sproviero, Eduardo M. |
author_facet |
Sproviero, Eduardo M. Burton, Gerardo |
author_role |
author |
author2 |
Burton, Gerardo |
author2_role |
author |
dc.subject.none.fl_str_mv |
NBO |
topic |
NBO |
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 contributions of stereoelectronic interactions to several molecular properties are used to analyze the propagation of information between different parts of the uracil molecule with a method that is based on the natural bond orbital (NBO) deletion technique. The emphasis is not on the effect of the contributions of localized orbitals to selected properties but rather on their interactions, giving information that is complementary to that resulting from a standard localized molecular orbital contribution. The analysis of how information between orbitals is transmitted throughout the molecule allows interpretation of the ways in which an interaction can affect a molecular property localized in the same region or in a different region of the molecule. A network of stereoelectronic interactions was identified in the uracil molecule, and the relative influences of the interactions that transmit information between different parts of the molecule were evaluated. An analysis was performed over localized properties on atoms and bonds of the two carbonyl groups, namely bond orders, distribution of electronic charge, and NMR shielding tensors. Interactions n(N3) → π*(C4=O) and n(N1) → π*(C5=C6) were the most important delocalizations that carry information concerning the change of substituents at C-5, whereas interactions n(N1) → π*(C2=O) and n(N3) rarr; π*(C2=O) were those mainly responsible for transmitting this information to the C-2 uracil carbonyl (C2=O) properties. Fil: Sproviero, Eduardo M.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina Fil: Burton, Gerardo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina |
description |
The contributions of stereoelectronic interactions to several molecular properties are used to analyze the propagation of information between different parts of the uracil molecule with a method that is based on the natural bond orbital (NBO) deletion technique. The emphasis is not on the effect of the contributions of localized orbitals to selected properties but rather on their interactions, giving information that is complementary to that resulting from a standard localized molecular orbital contribution. The analysis of how information between orbitals is transmitted throughout the molecule allows interpretation of the ways in which an interaction can affect a molecular property localized in the same region or in a different region of the molecule. A network of stereoelectronic interactions was identified in the uracil molecule, and the relative influences of the interactions that transmit information between different parts of the molecule were evaluated. An analysis was performed over localized properties on atoms and bonds of the two carbonyl groups, namely bond orders, distribution of electronic charge, and NMR shielding tensors. Interactions n(N3) → π*(C4=O) and n(N1) → π*(C5=C6) were the most important delocalizations that carry information concerning the change of substituents at C-5, whereas interactions n(N1) → π*(C2=O) and n(N3) rarr; π*(C2=O) were those mainly responsible for transmitting this information to the C-2 uracil carbonyl (C2=O) properties. |
publishDate |
2003 |
dc.date.none.fl_str_mv |
2003-07 |
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/11336/88190 Sproviero, Eduardo M.; Burton, Gerardo; Stereoelectronic interactions and molecular properties: An NBO-based study of uracil; American Chemical Society; Journal of Physical Chemistry A; 107; 29; 7-2003; 5544-5554 1089-5639 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/88190 |
identifier_str_mv |
Sproviero, Eduardo M.; Burton, Gerardo; Stereoelectronic interactions and molecular properties: An NBO-based study of uracil; American Chemical Society; Journal of Physical Chemistry A; 107; 29; 7-2003; 5544-5554 1089-5639 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://pubs.acs.org/doi/abs/10.1021/jp0271763 info:eu-repo/semantics/altIdentifier/doi/10.1021/jp0271763 |
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 |
dc.publisher.none.fl_str_mv |
American Chemical Society |
publisher.none.fl_str_mv |
American Chemical Society |
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_ |
1844613363771899904 |
score |
13.070432 |