Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/10542 |
Resumo: | In this work is described the intermolecular interactions and the molecular topology present in the crystal packing of 3-amine-4-halo-5-methylisoxazoles. First was described the obtention of the 3-amine-4-halo-5-methylisoxazoles by halogenations of the compound 3-amine-5-methylisoxazol with N-chlorosuccinimide, N-bromosuccinimide and N-iodoosuccinimide. The crystal packing of the 3-amine-4- halo-5-methylisoxazoles show a great variety of intermolecular interactions such as: hydrogen bonding, halogen bonding, π π interactions and C-H π interactions. Further analysis of crystal packing showed that these compounds have a molecular coordination number equal to 14. The correlation between molecule molecule energy contact and the contact area between the molecules showed that, with the exception of dimmers formed by strong hydrogen bonds, all the other interactions have a large dependence of the contact area. The melting enthalpy of the 3-amine-4- halo-5-methylisoxazoles grows with the increases of the total energy of the contacts of the clusters, showing that these physic property depends of the intermolecular interactions present in the crystal. The analysis of theory levels used to determine the molecule molecule energies contact demonstrates that, when is used the method counterpoise for basis set superposition error (BSSE), the level of theory MP2/Augcc- pVDZ show energy values very close to the energy at the MP2/cc-pVTZ level of theory. The functional B97-D and ωB97X-D, based on the DFT theory, also showed satisfactory energy values, very close to those obtained by MP2. |
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Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóisIntermolecular interactions and molecular topology in crystal packing of 3-amine-4-halo-5-methylisoxazolesIsoxazóisInterações intermolecularesTopologia molecularMP2IsoxazolesIntermolecular interactionsMolecular topologyCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIn this work is described the intermolecular interactions and the molecular topology present in the crystal packing of 3-amine-4-halo-5-methylisoxazoles. First was described the obtention of the 3-amine-4-halo-5-methylisoxazoles by halogenations of the compound 3-amine-5-methylisoxazol with N-chlorosuccinimide, N-bromosuccinimide and N-iodoosuccinimide. The crystal packing of the 3-amine-4- halo-5-methylisoxazoles show a great variety of intermolecular interactions such as: hydrogen bonding, halogen bonding, π π interactions and C-H π interactions. Further analysis of crystal packing showed that these compounds have a molecular coordination number equal to 14. The correlation between molecule molecule energy contact and the contact area between the molecules showed that, with the exception of dimmers formed by strong hydrogen bonds, all the other interactions have a large dependence of the contact area. The melting enthalpy of the 3-amine-4- halo-5-methylisoxazoles grows with the increases of the total energy of the contacts of the clusters, showing that these physic property depends of the intermolecular interactions present in the crystal. The analysis of theory levels used to determine the molecule molecule energies contact demonstrates that, when is used the method counterpoise for basis set superposition error (BSSE), the level of theory MP2/Augcc- pVDZ show energy values very close to the energy at the MP2/cc-pVTZ level of theory. The functional B97-D and ωB97X-D, based on the DFT theory, also showed satisfactory energy values, very close to those obtained by MP2.Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorNeste trabalho são descritas as interações intermoleculares e a topologia molecular referente ao empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis. Primeiramente foi descrita a obtenção dos 3-amino-4-halo-5-metilisoxazóis através da halogenação do composto 3-amino-5-metilizoxazol com N-clorosuccinimida, Nbromosuccinimida e N-iodosuccinimida. O empacotamento cristalino dos 3-amino-4- halo-5-metilisoxazóis apresentou uma grande diversidade de interações intermoleculares incluindo: ligações de hidrogênio, ligações de halogênio, interações π π e C-H π. Uma análise mais detalhada do empacotamento cristalino demonstrou que estes compostos apresentam um número de coordenação molecular igual a 14. A correlação entre a energia de contato molécula molécula e a área de contato entre as moléculas demonstrou que, com exceção dos dímeros formados por ligações de hidrogênio fortes, as demais interações apresentam uma grande dependência da área de contato. A entalpia de fusão dos 3-amino-4-halo-5- metilisoxazol aumenta com o aumento da energia total do cluster demonstrando que esta propriedade física está vinculada as interações intermoleculares presentes no cristal. A análise dos níveis de teoria utilizados para determinar as energias de contato molécula molécula demonstra que ,quando utilizado o método counterpoise para o erro de sobreposição de bases (BSSE), o nível de teoria MP2/Aug-cc-pVDZ apresentou valores de energia muito próximos ao do nível MP2/cc-pVTZ. Os funcionais B97-D E ωB97X-D, baseados na teoria DFT também apresentaram valores de energia satisfatórios, muito próximos aos obtidos pelo MP2.Universidade Federal de Santa MariaBRQuímicaUFSMPrograma de Pós-Graduação em QuímicaMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Ducati, Lucas Coluccihttp://lattes.cnpq.br/1605430966535142Frizzo, Clarissa Piccininhttp://lattes.cnpq.br/0029279904716491Meyer, Alexandre Robison2017-05-102017-05-102013-02-26info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfapplication/pdfMEYER, Alexandre Robison. Intermolecular interactions and molecular topology in crystal packing of 3-amine-4-halo-5-methylisoxazoles. 2013. 141 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013.http://repositorio.ufsm.br/handle/1/10542porinfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2023-06-12T19:49:15Zoai:repositorio.ufsm.br:1/10542Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-06-12T19:49:15Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis Intermolecular interactions and molecular topology in crystal packing of 3-amine-4-halo-5-methylisoxazoles |
title |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis |
spellingShingle |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis Meyer, Alexandre Robison Isoxazóis Interações intermoleculares Topologia molecular MP2 Isoxazoles Intermolecular interactions Molecular topology CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis |
title_full |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis |
title_fullStr |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis |
title_full_unstemmed |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis |
title_sort |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis |
author |
Meyer, Alexandre Robison |
author_facet |
Meyer, Alexandre Robison |
author_role |
author |
dc.contributor.none.fl_str_mv |
Martins, Marcos Antonio Pinto http://lattes.cnpq.br/6457412713967642 Ducati, Lucas Colucci http://lattes.cnpq.br/1605430966535142 Frizzo, Clarissa Piccinin http://lattes.cnpq.br/0029279904716491 |
dc.contributor.author.fl_str_mv |
Meyer, Alexandre Robison |
dc.subject.por.fl_str_mv |
Isoxazóis Interações intermoleculares Topologia molecular MP2 Isoxazoles Intermolecular interactions Molecular topology CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Isoxazóis Interações intermoleculares Topologia molecular MP2 Isoxazoles Intermolecular interactions Molecular topology CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work is described the intermolecular interactions and the molecular topology present in the crystal packing of 3-amine-4-halo-5-methylisoxazoles. First was described the obtention of the 3-amine-4-halo-5-methylisoxazoles by halogenations of the compound 3-amine-5-methylisoxazol with N-chlorosuccinimide, N-bromosuccinimide and N-iodoosuccinimide. The crystal packing of the 3-amine-4- halo-5-methylisoxazoles show a great variety of intermolecular interactions such as: hydrogen bonding, halogen bonding, π π interactions and C-H π interactions. Further analysis of crystal packing showed that these compounds have a molecular coordination number equal to 14. The correlation between molecule molecule energy contact and the contact area between the molecules showed that, with the exception of dimmers formed by strong hydrogen bonds, all the other interactions have a large dependence of the contact area. The melting enthalpy of the 3-amine-4- halo-5-methylisoxazoles grows with the increases of the total energy of the contacts of the clusters, showing that these physic property depends of the intermolecular interactions present in the crystal. The analysis of theory levels used to determine the molecule molecule energies contact demonstrates that, when is used the method counterpoise for basis set superposition error (BSSE), the level of theory MP2/Augcc- pVDZ show energy values very close to the energy at the MP2/cc-pVTZ level of theory. The functional B97-D and ωB97X-D, based on the DFT theory, also showed satisfactory energy values, very close to those obtained by MP2. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-02-26 2017-05-10 2017-05-10 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
MEYER, Alexandre Robison. Intermolecular interactions and molecular topology in crystal packing of 3-amine-4-halo-5-methylisoxazoles. 2013. 141 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013. http://repositorio.ufsm.br/handle/1/10542 |
identifier_str_mv |
MEYER, Alexandre Robison. Intermolecular interactions and molecular topology in crystal packing of 3-amine-4-halo-5-methylisoxazoles. 2013. 141 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013. |
url |
http://repositorio.ufsm.br/handle/1/10542 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1805922093812940800 |