Pyrogallol[4]arenes are macrocycles with high potential as building blocks for nanocapsules. We theoretically studied the dimeric precursors of 2,8,14,20-tetramethylpyrogallol[4]arene and 2,8,10,14-tetraphenylpyrogallol[4]arene to understand the dynamics of assembly of these compounds, and calculate...

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Autores:
Cazar, Robert A.; 1 ESPOCH, Facultad de Ciencias, Panamericana Sur Km 1.5, Riobamba, Ecuador. 2 Grupo Ecuatoriano para el Estudio Experimental y Teórico de Nanosistemas,-GETNano.
Torres, F. Javier
Tipo de recurso:
Article of journal
Fecha de publicación:
2014
Institución:
Pontificia Universidad Javeriana
Repositorio:
Repositorio Universidad Javeriana
Idioma:
eng
OAI Identifier:
oai:repository.javeriana.edu.co:10554/31775
Acceso en línea:
http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8472
http://hdl.handle.net/10554/31775
Palabra clave:
null
Pyrogallol[4]arenes; computational chemistry; nanocapsules.
null
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openAccess
License
Atribución-NoComercial-SinDerivadas 4.0 Internacional
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oai_identifier_str oai:repository.javeriana.edu.co:10554/31775
network_acronym_str JAVERIANA2
network_name_str Repositorio Universidad Javeriana
repository_id_str
spelling Atribución-NoComercial-SinDerivadas 4.0 Internacionalinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2nullCazar, Robert A.; 1 ESPOCH, Facultad de Ciencias, Panamericana Sur Km 1.5, Riobamba, Ecuador. 2 Grupo Ecuatoriano para el Estudio Experimental y Teórico de Nanosistemas,-GETNano.Torres, F. Javier2018-02-24T16:00:37Z2020-04-15T18:08:22Z2018-02-24T16:00:37Z2020-04-15T18:08:22Z2014-05-12http://revistas.javeriana.edu.co/index.php/scientarium/article/view/847210.11144/Javeriana.SC19-2.tirb2027-13520122-7483http://hdl.handle.net/10554/31775PDFapplication/pdfengPontificia Universidad Javerianahttp://revistas.javeriana.edu.co/index.php/scientarium/article/view/8472/7411Universitas Scientiarum; Vol 19, No 2 (2014); 133-137Universitas Scientiarum; Vol 19, No 2 (2014); 133-137Universitas Scientiarum; Vol 19, No 2 (2014); 133-137nullPyrogallol[4]arenes; computational chemistry; nanocapsules.nullnullnullnullhttp://purl.org/coar/version/c_970fb48d4fbd8a85Artículo de revistahttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1info:eu-repo/semantics/articleTheoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometryPyrogallol[4]arenes are macrocycles with high potential as building blocks for nanocapsules. We theoretically studied the dimeric precursors of 2,8,14,20-tetramethylpyrogallol[4]arene and 2,8,10,14-tetraphenylpyrogallol[4]arene to understand the dynamics of assembly of these compounds, and calculated the potential energy curves along the torsion angle of the (R-pyrogallol)CH–(R-pyrogallol) dimeric bond at the B3LYP/6-311G(d,p) level of theory. We found that the energy barriers for free rotation around the selected bond are 0.00133 Hartrees for the alkyl-substituted dimer and 0.77879 Hartrees for the aryl-substituted dimer. These values imply that the free rotation around the selected bond exists for the first dimer but not for the second one. Because the orientation of the substituent and the pyrogallol ring around this bond are likely to determine the geometry of the final structure, we propose that the alkyl-substituted compound will most likely adopt a crown-shaped geometry whereas the aryl-substituted compound will adopt a chair-shaped geometry. These predictions concur with experimental evidence, which shows that the geometry of pyrogallol[4]arenes depends on the substituents attached to them.10554/31775oai:repository.javeriana.edu.co:10554/317752023-03-28 16:15:32.123Repositorio Institucional - Pontificia Universidad Javerianarepositorio@javeriana.edu.co
dc.title.english.eng.fl_str_mv Theoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometry
dc.creator.fl_str_mv Cazar, Robert A.; 1 ESPOCH, Facultad de Ciencias, Panamericana Sur Km 1.5, Riobamba, Ecuador. 2 Grupo Ecuatoriano para el Estudio Experimental y Teórico de Nanosistemas,-GETNano.
Torres, F. Javier
dc.contributor.author.none.fl_str_mv Cazar, Robert A.; 1 ESPOCH, Facultad de Ciencias, Panamericana Sur Km 1.5, Riobamba, Ecuador. 2 Grupo Ecuatoriano para el Estudio Experimental y Teórico de Nanosistemas,-GETNano.
Torres, F. Javier
dc.contributor.none.fl_str_mv null
dc.subject.eng.fl_str_mv null
Pyrogallol[4]arenes; computational chemistry; nanocapsules.
null
topic null
Pyrogallol[4]arenes; computational chemistry; nanocapsules.
null
spellingShingle null
Pyrogallol[4]arenes; computational chemistry; nanocapsules.
null
description Pyrogallol[4]arenes are macrocycles with high potential as building blocks for nanocapsules. We theoretically studied the dimeric precursors of 2,8,14,20-tetramethylpyrogallol[4]arene and 2,8,10,14-tetraphenylpyrogallol[4]arene to understand the dynamics of assembly of these compounds, and calculated the potential energy curves along the torsion angle of the (R-pyrogallol)CH–(R-pyrogallol) dimeric bond at the B3LYP/6-311G(d,p) level of theory. We found that the energy barriers for free rotation around the selected bond are 0.00133 Hartrees for the alkyl-substituted dimer and 0.77879 Hartrees for the aryl-substituted dimer. These values imply that the free rotation around the selected bond exists for the first dimer but not for the second one. Because the orientation of the substituent and the pyrogallol ring around this bond are likely to determine the geometry of the final structure, we propose that the alkyl-substituted compound will most likely adopt a crown-shaped geometry whereas the aryl-substituted compound will adopt a chair-shaped geometry. These predictions concur with experimental evidence, which shows that the geometry of pyrogallol[4]arenes depends on the substituents attached to them.
publishDate 2014
dc.date.created.none.fl_str_mv 2014-05-12
dc.date.accessioned.none.fl_str_mv 2018-02-24T16:00:37Z
2020-04-15T18:08:22Z
dc.date.available.none.fl_str_mv 2018-02-24T16:00:37Z
2020-04-15T18:08:22Z
dc.type.coar.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
dc.type.hasversion.none.fl_str_mv http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.local.spa.fl_str_mv Artículo de revista
dc.type.coar.none.fl_str_mv http://purl.org/coar/resource_type/c_6501
dc.type.driver.none.fl_str_mv info:eu-repo/semantics/article
format http://purl.org/coar/resource_type/c_6501
dc.identifier.none.fl_str_mv http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8472
10.11144/Javeriana.SC19-2.tirb
dc.identifier.issn.none.fl_str_mv 2027-1352
0122-7483
dc.identifier.uri.none.fl_str_mv http://hdl.handle.net/10554/31775
url http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8472
http://hdl.handle.net/10554/31775
identifier_str_mv 10.11144/Javeriana.SC19-2.tirb
2027-1352
0122-7483
dc.language.iso.none.fl_str_mv eng
language eng
dc.relation.uri.none.fl_str_mv http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8472/7411
dc.relation.citationissue.eng.fl_str_mv Universitas Scientiarum; Vol 19, No 2 (2014); 133-137
dc.relation.citationissue.spa.fl_str_mv Universitas Scientiarum; Vol 19, No 2 (2014); 133-137
dc.relation.citationissue.por.fl_str_mv Universitas Scientiarum; Vol 19, No 2 (2014); 133-137
dc.rights.licence.*.fl_str_mv Atribución-NoComercial-SinDerivadas 4.0 Internacional
dc.rights.accessrights.none.fl_str_mv info:eu-repo/semantics/openAccess
dc.rights.coar.spa.fl_str_mv http://purl.org/coar/access_right/c_abf2
rights_invalid_str_mv Atribución-NoComercial-SinDerivadas 4.0 Internacional
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.spa.fl_str_mv PDF
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.coverage.none.fl_str_mv null
null
null
dc.publisher.eng.fl_str_mv Pontificia Universidad Javeriana
institution Pontificia Universidad Javeriana
repository.name.fl_str_mv Repositorio Institucional - Pontificia Universidad Javeriana
repository.mail.fl_str_mv repositorio@javeriana.edu.co
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