Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis
Ano de defesa: | 2013 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | 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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2017-05-102017-05-102013-02-26MEYER, 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/1/10542In 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.Neste 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.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaIsoxazóisInterações intermolecularesTopologia molecularMP2IsoxazolesIntermolecular interactionsMolecular topologyCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAInterações 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-methylisoxazolesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Ducati, Lucas Coluccihttp://lattes.cnpq.br/1605430966535142Frizzo, Clarissa Piccininhttp://lattes.cnpq.br/0029279904716491http://lattes.cnpq.br/5028033620704356Meyer, Alexandre Robison100600000000400500300300500c28419d9-6027-4f9c-acd2-76e8067a85d1a4dc1194-19b0-4628-a4b0-7e5b1a3138057c949bdf-acf1-47c7-bc37-72c6788cd937d15b5067-d5ab-4a9f-9e0c-a1122d544ef0info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALMEYER, ALEXANDRE ROBISON.pdfapplication/pdf5840316http://repositorio.ufsm.br/bitstream/1/10542/1/MEYER%2c%20ALEXANDRE%20ROBISON.pdf29f318bb66cf3f0aa703d85a8751e043MD51TEXTMEYER, ALEXANDRE ROBISON.pdf.txtMEYER, ALEXANDRE ROBISON.pdf.txtExtracted texttext/plain182712http://repositorio.ufsm.br/bitstream/1/10542/2/MEYER%2c%20ALEXANDRE%20ROBISON.pdf.txt080671e406f899a96afb8816953188b6MD52THUMBNAILMEYER, ALEXANDRE ROBISON.pdf.jpgMEYER, ALEXANDRE ROBISON.pdf.jpgIM Thumbnailimage/jpeg5259http://repositorio.ufsm.br/bitstream/1/10542/3/MEYER%2c%20ALEXANDRE%20ROBISON.pdf.jpgbddfcd82dbce926a3871f09d697aafdeMD531/105422023-06-12 16:49:15.72oai: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:2023-06-12T19:49:15Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Interações intermoleculares e topologia molecular no empacotamento cristalino de 3-amino-4-halo-5-metilisoxazóis |
dc.title.alternative.eng.fl_str_mv |
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.advisor1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.referee1.fl_str_mv |
Ducati, Lucas Colucci |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/1605430966535142 |
dc.contributor.referee2.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0029279904716491 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5028033620704356 |
dc.contributor.author.fl_str_mv |
Meyer, Alexandre Robison |
contributor_str_mv |
Martins, Marcos Antonio Pinto Ducati, Lucas Colucci Frizzo, Clarissa Piccinin |
dc.subject.por.fl_str_mv |
Isoxazóis Interações intermoleculares Topologia molecular MP2 |
topic |
Isoxazóis Interações intermoleculares Topologia molecular MP2 Isoxazoles Intermolecular interactions Molecular topology CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Isoxazoles Intermolecular interactions Molecular topology |
dc.subject.cnpq.fl_str_mv |
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.issued.fl_str_mv |
2013-02-26 |
dc.date.accessioned.fl_str_mv |
2017-05-10 |
dc.date.available.fl_str_mv |
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.citation.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. |
dc.identifier.uri.fl_str_mv |
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 |
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