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...
- 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
- Rights
- openAccess
- License
- Atribución-NoComercial-SinDerivadas 4.0 Internacional
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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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1811670651905245184 |