Theoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometry
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 calculat...
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Pontificia Universidad Javeriana
2014-05-01
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| Series: | Universitas Scientiarum |
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| Online Access: | http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8472/7411 |
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| author | Robert A. Cazar F. Javier Torres |
| author_facet | Robert A. Cazar F. Javier Torres |
| author_sort | Robert A. Cazar |
| collection | DOAJ |
| 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. |
| format | Article |
| id | doaj-art-bd87b08b59f744ca98b0f6d0ac7fd5cd |
| institution | OA Journals |
| issn | 0122-7483 0122-7483 |
| language | English |
| publishDate | 2014-05-01 |
| publisher | Pontificia Universidad Javeriana |
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| series | Universitas Scientiarum |
| spelling | doaj-art-bd87b08b59f744ca98b0f6d0ac7fd5cd2025-08-20T02:00:29ZengPontificia Universidad JaverianaUniversitas Scientiarum0122-74830122-74832014-05-0119113313710.11144/Javeriana.SC19-2.tirbTheoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometryRobert A. Cazar0 F. Javier Torres1 ESPOCH, Facultad de Ciencias, Panamericana Sur Km 1.5, Riobamba, Ecuador Grupo de Química Computacional y Teórica (QCT-USFQ), Universidad San Francisco de Quito, Diego de Robles y Vía Interoceánica, Quito 17-1200-841, Ecuador.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.http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8472/7411Pyrogallol[4]arenescomputational chemistrynanocapsules |
| spellingShingle | Robert A. Cazar F. Javier Torres Theoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometry Universitas Scientiarum Pyrogallol[4]arenes computational chemistry nanocapsules |
| title | Theoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometry |
| title_full | Theoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometry |
| title_fullStr | Theoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometry |
| title_full_unstemmed | Theoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometry |
| title_short | Theoretical indications on the relationship between pyrogallol[4]arenes dynamics of assembling and geometry |
| title_sort | theoretical indications on the relationship between pyrogallol 4 arenes dynamics of assembling and geometry |
| topic | Pyrogallol[4]arenes computational chemistry nanocapsules |
| url | http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8472/7411 |
| work_keys_str_mv | AT robertacazar theoreticalindicationsontherelationshipbetweenpyrogallol4arenesdynamicsofassemblingandgeometry AT fjaviertorres theoreticalindicationsontherelationshipbetweenpyrogallol4arenesdynamicsofassemblingandgeometry |