Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos
Autor(a) principal: | |
---|---|
Data de Publicação: | 2018 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/29840 |
Resumo: | This investigation reports the proposal of a new method to obtain quantitative indexes of similarity in crystals, using the supramolecular cluster as study demarcation. A series of tert-butyl pyrazoles were used as models for the proposal and application of the indexes. The indexes (IX) consider geometric (ID), contact area (IC) and stabilization energy (IG) parameters. In addition, a multiparameter index of similarity (IDCG) was proposed – in which the inheritance of the initial parameters is carried – to aid in the comparison between structures with only one final value. It was observed that the demarcation problem, in relation to the size of the studied system, is one of the problems in studies of supramolecular similarity. It was possible to establish a similarity range for the proposed indexes, where IX ≥ 0.80 (high similarity); 0.80 > IX > 0.60 (intermediate); IX < 0.60 (low), where X = D, C, G or DCG. It was observed that two highly similar systems must have an isostructural, isotopological and isoenergetic behavior. Similarity indexes were applied in a series of polymorphs, with different numbers of molecules in the asymmetric unit. It was determined different regions of similarity within the polymorphism phenomenon, being possible to determine the boundaries between quasi-isostructural polymorphs. A new similarity index – based on the types and normalized contribution of the total intermolecular interactions of each cluster (IQ) – was proposed. The IQ indicates to be a versatile tool and applicable even for systems that do not share any similarity. In addition, mechanisms of crystallization of new polymorphs have been proposed. It was possible to indicate the time in which the different triazene polymorphs (1IA and 1IIA) are formed during the nucleation process. Similarity indexes were also applied for the bisphenyltriazenes, and mechanisms of crystallization were proposed to study the selfassembly of this series. The hydrogen interactions between the triazenes and the stacking are present in almost all examples at some point of crystallization process. It was possible to evaluate the unique characteristics of a pyridine solvate and to compare it with the structure without solvent. The IDCG was presented as a robust comparative index for all the comparisons, taking into account the particularities of the systems in its final value. The multilinear correlation indicated a high contribution of the energy parameter (43%) to the final value of the IDCG, followed by geometric (31%) and contact area (27%) parameters. Therefore, the IG is an indispensable parameter in the analysis of supramolecular similarity of crystalline structures. |
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2023-08-03T16:14:51Z2023-08-03T16:14:51Z2018-06-20http://repositorio.ufsm.br/handle/1/29840This investigation reports the proposal of a new method to obtain quantitative indexes of similarity in crystals, using the supramolecular cluster as study demarcation. A series of tert-butyl pyrazoles were used as models for the proposal and application of the indexes. The indexes (IX) consider geometric (ID), contact area (IC) and stabilization energy (IG) parameters. In addition, a multiparameter index of similarity (IDCG) was proposed – in which the inheritance of the initial parameters is carried – to aid in the comparison between structures with only one final value. It was observed that the demarcation problem, in relation to the size of the studied system, is one of the problems in studies of supramolecular similarity. It was possible to establish a similarity range for the proposed indexes, where IX ≥ 0.80 (high similarity); 0.80 > IX > 0.60 (intermediate); IX < 0.60 (low), where X = D, C, G or DCG. It was observed that two highly similar systems must have an isostructural, isotopological and isoenergetic behavior. Similarity indexes were applied in a series of polymorphs, with different numbers of molecules in the asymmetric unit. It was determined different regions of similarity within the polymorphism phenomenon, being possible to determine the boundaries between quasi-isostructural polymorphs. A new similarity index – based on the types and normalized contribution of the total intermolecular interactions of each cluster (IQ) – was proposed. The IQ indicates to be a versatile tool and applicable even for systems that do not share any similarity. In addition, mechanisms of crystallization of new polymorphs have been proposed. It was possible to indicate the time in which the different triazene polymorphs (1IA and 1IIA) are formed during the nucleation process. Similarity indexes were also applied for the bisphenyltriazenes, and mechanisms of crystallization were proposed to study the selfassembly of this series. The hydrogen interactions between the triazenes and the stacking are present in almost all examples at some point of crystallization process. It was possible to evaluate the unique characteristics of a pyridine solvate and to compare it with the structure without solvent. The IDCG was presented as a robust comparative index for all the comparisons, taking into account the particularities of the systems in its final value. The multilinear correlation indicated a high contribution of the energy parameter (43%) to the final value of the IDCG, followed by geometric (31%) and contact area (27%) parameters. Therefore, the IG is an indispensable parameter in the analysis of supramolecular similarity of crystalline structures.Este trabalho relata a proposta de um novo método para obtenção de índices quantitativos de similaridade em cristais, utilizando o cluster supramolecular como demarcação do estudo. Uma série de tert-butil pirazóis foram utilizados como modelos para a proposta e aplicação dos índices. Os índices (IX) consideram parâmetros geométricos (ID), de área de contato (IC) e de energia de estabilização (IG). Além disso, um índice multiparâmetro de similaridade (IDCG) foi proposto, em que a herança dos parâmetros iniciais está embutida, para auxiliar na comparação entre estruturas com apenas um valor final. Foi observado que o problema de demarcação, em relação ao tamanho do sistema estudado, é um dos problemas em estudos de similaridade supramolecular. Foi possível estabelecer uma faixa de similaridade para os índices propostos, em que IX ≥ 0,80 (alta similaridade); 0,80 > IX > 0,60 (Intermediária); IX < 0,60 (baixa), sendo X = D, C, G ou DCG. Foi observado que dois sistemas altamente similares devem ter um comportamento isoestrutural, isotopológico e isoenergético. Os índices de similaridade foram aplicados em uma série de polimorfos, com diferentes números de moléculas na unidade assimétrica. Foi determinada diferentes regiões de similaridade dentro do fenômeno de polimorfismo, sendo possível determinar as fronteiras entre os polimorfos com caráter quasi-isoestrutural. Um novo índice de similaridade, baseado nos tipos e contribuição normalizada das interações intermoleculares totais de cada cluster (IQ), foi proposto. O IQ indica ser uma ferramenta versátil e aplicável mesmo para sistemas que não compartilham nenhuma similaridade. Além disso, mecanismos de cristalização de novos polimorfos foram propostos. Foi indicado o momento em que os diferentes polimorfos de triazeno (1IA e 1IIA) são formados durante o processo de nucleação. Índices de similaridade também foram aplicados para uma série de bis-feniltriazenos, e mecanismos de cristalização foram propostos para estudar a autoassociação dessa série. As interações de hidrogênio entre os triazenos e o empilhamento está presente em quase todos os exemplos, em algum momento da cristalização. Foi possível avaliar as características únicas de um solvato de piridina e compará-la com a estrutura sem solvente. O IDCG apresentou-se como um índice comparativo robusto para todas as comparações realizadas, levando em consideração as particularidades dos sistemas no valor final. A correlação multilinear indicou alta contribuição do parâmetro energético (43 %) para o valor final do IDCG, seguido do geométrico (31 %) e de área de contato (27 %). Assim, o índice IG se apresenta como parâmetro indispensável na análise de similaridade supramolecular em estruturas cristalinas.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessEngenharia de cristaisSimilaridade supramolecularPolimorfosCristalizaçãoAutoassociaçãoSolvatoCrystal engineeringSupramolecular similarityPolymorphsCrystallizationSelf-assemblySolvateCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASimilaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativosSimilarity of supramolecular structures in organic crystals: proposal of quantitative indexesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Frizzo, Clarissa PiccininBonacorso, Helio GauzeHörner, ManfredoPereira, Claudio Martin Pereira deRocha, Gerd Brunohttp://lattes.cnpq.br/5447265840552788Salbego, Paulo Roberto dos Santos100600000000600600600600600600600600c28419d9-6027-4f9c-acd2-76e8067a85d1a6f4009f-484e-4ade-a30e-7e16be2c3086d547141e-3d22-4b07-ad8d-c6e60d6d1dd9dbcce58b-96b0-4f45-a78d-ca6f339e038dfbc928b5-4959-4411-a1cd-dc19be3562526844a829-3e85-40b1-ae5f-660be49718736807c011-6f1b-4f0e-b786-fc7d24e9ff02reponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos |
dc.title.alternative.eng.fl_str_mv |
Similarity of supramolecular structures in organic crystals: proposal of quantitative indexes |
title |
Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos |
spellingShingle |
Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos Salbego, Paulo Roberto dos Santos Engenharia de cristais Similaridade supramolecular Polimorfos Cristalização Autoassociação Solvato Crystal engineering Supramolecular similarity Polymorphs Crystallization Self-assembly Solvate CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos |
title_full |
Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos |
title_fullStr |
Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos |
title_full_unstemmed |
Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos |
title_sort |
Similaridade de estruturas supramoleculares em cristais orgânicos: proposta de índices quantitativos |
author |
Salbego, Paulo Roberto dos Santos |
author_facet |
Salbego, Paulo Roberto dos Santos |
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.advisor-co1.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.referee1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.referee2.fl_str_mv |
Hörner, Manfredo |
dc.contributor.referee3.fl_str_mv |
Pereira, Claudio Martin Pereira de |
dc.contributor.referee4.fl_str_mv |
Rocha, Gerd Bruno |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5447265840552788 |
dc.contributor.author.fl_str_mv |
Salbego, Paulo Roberto dos Santos |
contributor_str_mv |
Martins, Marcos Antonio Pinto Frizzo, Clarissa Piccinin Bonacorso, Helio Gauze Hörner, Manfredo Pereira, Claudio Martin Pereira de Rocha, Gerd Bruno |
dc.subject.por.fl_str_mv |
Engenharia de cristais Similaridade supramolecular Polimorfos Cristalização Autoassociação Solvato |
topic |
Engenharia de cristais Similaridade supramolecular Polimorfos Cristalização Autoassociação Solvato Crystal engineering Supramolecular similarity Polymorphs Crystallization Self-assembly Solvate CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Crystal engineering Supramolecular similarity Polymorphs Crystallization Self-assembly Solvate |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This investigation reports the proposal of a new method to obtain quantitative indexes of similarity in crystals, using the supramolecular cluster as study demarcation. A series of tert-butyl pyrazoles were used as models for the proposal and application of the indexes. The indexes (IX) consider geometric (ID), contact area (IC) and stabilization energy (IG) parameters. In addition, a multiparameter index of similarity (IDCG) was proposed – in which the inheritance of the initial parameters is carried – to aid in the comparison between structures with only one final value. It was observed that the demarcation problem, in relation to the size of the studied system, is one of the problems in studies of supramolecular similarity. It was possible to establish a similarity range for the proposed indexes, where IX ≥ 0.80 (high similarity); 0.80 > IX > 0.60 (intermediate); IX < 0.60 (low), where X = D, C, G or DCG. It was observed that two highly similar systems must have an isostructural, isotopological and isoenergetic behavior. Similarity indexes were applied in a series of polymorphs, with different numbers of molecules in the asymmetric unit. It was determined different regions of similarity within the polymorphism phenomenon, being possible to determine the boundaries between quasi-isostructural polymorphs. A new similarity index – based on the types and normalized contribution of the total intermolecular interactions of each cluster (IQ) – was proposed. The IQ indicates to be a versatile tool and applicable even for systems that do not share any similarity. In addition, mechanisms of crystallization of new polymorphs have been proposed. It was possible to indicate the time in which the different triazene polymorphs (1IA and 1IIA) are formed during the nucleation process. Similarity indexes were also applied for the bisphenyltriazenes, and mechanisms of crystallization were proposed to study the selfassembly of this series. The hydrogen interactions between the triazenes and the stacking are present in almost all examples at some point of crystallization process. It was possible to evaluate the unique characteristics of a pyridine solvate and to compare it with the structure without solvent. The IDCG was presented as a robust comparative index for all the comparisons, taking into account the particularities of the systems in its final value. The multilinear correlation indicated a high contribution of the energy parameter (43%) to the final value of the IDCG, followed by geometric (31%) and contact area (27%) parameters. Therefore, the IG is an indispensable parameter in the analysis of supramolecular similarity of crystalline structures. |
publishDate |
2018 |
dc.date.issued.fl_str_mv |
2018-06-20 |
dc.date.accessioned.fl_str_mv |
2023-08-03T16:14:51Z |
dc.date.available.fl_str_mv |
2023-08-03T16:14:51Z |
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 |
http://repositorio.ufsm.br/handle/1/29840 |
url |
http://repositorio.ufsm.br/handle/1/29840 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 600 |
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dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional Manancial UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
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