Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues.
Autor(a) principal: | |
---|---|
Data de Publicação: | 2016 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFOP |
Texto Completo: | http://www.repositorio.ufop.br/handle/123456789/7069 |
Resumo: | We have here elucidated the crystal structures of five nostoclide analogues. A common feature in all compounds is a substituent at the para-position of the benzylidene group. Compounds with either bromine (3) or hydroxyl (4) as para-substituent crystallizes with Z’ ¼ 2 as result of conformerism. It was also observed that Z' > 1 in the compound with a para-dimethylamino substituent (1). However, its four crystallographically independent molecules are conformationally similar. They are not related by crystallographic symmetry due to the offset packing of their CeH … O]C nonclassical hydrogen bonded double chains. This compound (1) has also crystallized in a chiral space group (P21) despite the lack of a stereocenter. Such enantiomorphism phenomenon is related to the presence of only one of the two mirror benzyl conformations with phenyl ring at the equatorial position opposite the lactone oxygen atom. The molecular mean plane of nostoclide analogues has been featured by high level of planarity, except in the brominated compound where two twisted conformations occurred due to rotations on the single bond axis into benzylidene group. The benzyl conformation has been the greatest difference between the two crystallographically independent molecules of the para-hydroxylated compound (4). The crystal packing of the compounds is marked by double catemer motif assembled through CeH … O] C non-classical hydrogen bonds, although CeH … p interactions do play an important role in stabilizing the crystal packing of some compounds of the series. |
id |
UFOP_e29a32a00d90bc49ec701d9f36ae9642 |
---|---|
oai_identifier_str |
oai:localhost:123456789/7069 |
network_acronym_str |
UFOP |
network_name_str |
Repositório Institucional da UFOP |
repository_id_str |
3233 |
spelling |
Teixeira, Róbson RicardoBarbosa, Luiz Cláudio de AlmeidaAntolinez, Isabel ValeroCorrea, Rodrigo de SouzaMartins, Felipe TerraDoriguetto, Antônio Carlos2016-11-07T13:20:26Z2016-11-07T13:20:26Z2016TEIXEIRA, R. R. et al. Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. Journal of Molecular Structure, v. 1106, p. 291-299, 2016. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0022286015304014>. Acesso em: 26 set. 2016.0022-2860http://www.repositorio.ufop.br/handle/123456789/7069O periódico Journal of Molecular Structure concede permissão para depósito deste artigo no Repositório Institucional da UFOP. Número da licença: 3958741415552.info:eu-repo/semantics/openAccessNostoclidesButenolidesGama-lactonesGama-alkylidenebutenolidesCrystal structureConformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleWe have here elucidated the crystal structures of five nostoclide analogues. A common feature in all compounds is a substituent at the para-position of the benzylidene group. Compounds with either bromine (3) or hydroxyl (4) as para-substituent crystallizes with Z’ ¼ 2 as result of conformerism. It was also observed that Z' > 1 in the compound with a para-dimethylamino substituent (1). However, its four crystallographically independent molecules are conformationally similar. They are not related by crystallographic symmetry due to the offset packing of their CeH … O]C nonclassical hydrogen bonded double chains. This compound (1) has also crystallized in a chiral space group (P21) despite the lack of a stereocenter. Such enantiomorphism phenomenon is related to the presence of only one of the two mirror benzyl conformations with phenyl ring at the equatorial position opposite the lactone oxygen atom. The molecular mean plane of nostoclide analogues has been featured by high level of planarity, except in the brominated compound where two twisted conformations occurred due to rotations on the single bond axis into benzylidene group. The benzyl conformation has been the greatest difference between the two crystallographically independent molecules of the para-hydroxylated compound (4). The crystal packing of the compounds is marked by double catemer motif assembled through CeH … O] C non-classical hydrogen bonds, although CeH … p interactions do play an important role in stabilizing the crystal packing of some compounds of the series.porreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOPLICENSElicense.txtlicense.txttext/plain; charset=utf-8924http://www.repositorio.ufop.br/bitstream/123456789/7069/2/license.txt62604f8d955274beb56c80ce1ee5dcaeMD52ORIGINALARTIGO_ConfomerismEnantiomorphismDouble.pdfARTIGO_ConfomerismEnantiomorphismDouble.pdfapplication/pdf2524312http://www.repositorio.ufop.br/bitstream/123456789/7069/1/ARTIGO_ConfomerismEnantiomorphismDouble.pdf342ec8f6cb11128190d79006d735b10aMD51123456789/70692019-10-15 10:22:22.661oai:localhost: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ório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332019-10-15T14:22:22Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false |
dc.title.pt_BR.fl_str_mv |
Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. |
title |
Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. |
spellingShingle |
Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. Teixeira, Róbson Ricardo Nostoclides Butenolides Gama-lactones Gama-alkylidenebutenolides Crystal structure |
title_short |
Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. |
title_full |
Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. |
title_fullStr |
Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. |
title_full_unstemmed |
Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. |
title_sort |
Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. |
author |
Teixeira, Róbson Ricardo |
author_facet |
Teixeira, Róbson Ricardo Barbosa, Luiz Cláudio de Almeida Antolinez, Isabel Valero Correa, Rodrigo de Souza Martins, Felipe Terra Doriguetto, Antônio Carlos |
author_role |
author |
author2 |
Barbosa, Luiz Cláudio de Almeida Antolinez, Isabel Valero Correa, Rodrigo de Souza Martins, Felipe Terra Doriguetto, Antônio Carlos |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Teixeira, Róbson Ricardo Barbosa, Luiz Cláudio de Almeida Antolinez, Isabel Valero Correa, Rodrigo de Souza Martins, Felipe Terra Doriguetto, Antônio Carlos |
dc.subject.por.fl_str_mv |
Nostoclides Butenolides Gama-lactones Gama-alkylidenebutenolides Crystal structure |
topic |
Nostoclides Butenolides Gama-lactones Gama-alkylidenebutenolides Crystal structure |
description |
We have here elucidated the crystal structures of five nostoclide analogues. A common feature in all compounds is a substituent at the para-position of the benzylidene group. Compounds with either bromine (3) or hydroxyl (4) as para-substituent crystallizes with Z’ ¼ 2 as result of conformerism. It was also observed that Z' > 1 in the compound with a para-dimethylamino substituent (1). However, its four crystallographically independent molecules are conformationally similar. They are not related by crystallographic symmetry due to the offset packing of their CeH … O]C nonclassical hydrogen bonded double chains. This compound (1) has also crystallized in a chiral space group (P21) despite the lack of a stereocenter. Such enantiomorphism phenomenon is related to the presence of only one of the two mirror benzyl conformations with phenyl ring at the equatorial position opposite the lactone oxygen atom. The molecular mean plane of nostoclide analogues has been featured by high level of planarity, except in the brominated compound where two twisted conformations occurred due to rotations on the single bond axis into benzylidene group. The benzyl conformation has been the greatest difference between the two crystallographically independent molecules of the para-hydroxylated compound (4). The crystal packing of the compounds is marked by double catemer motif assembled through CeH … O] C non-classical hydrogen bonds, although CeH … p interactions do play an important role in stabilizing the crystal packing of some compounds of the series. |
publishDate |
2016 |
dc.date.accessioned.fl_str_mv |
2016-11-07T13:20:26Z |
dc.date.available.fl_str_mv |
2016-11-07T13:20:26Z |
dc.date.issued.fl_str_mv |
2016 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
TEIXEIRA, R. R. et al. Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. Journal of Molecular Structure, v. 1106, p. 291-299, 2016. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0022286015304014>. Acesso em: 26 set. 2016. |
dc.identifier.uri.fl_str_mv |
http://www.repositorio.ufop.br/handle/123456789/7069 |
dc.identifier.issn.none.fl_str_mv |
0022-2860 |
identifier_str_mv |
TEIXEIRA, R. R. et al. Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues. Journal of Molecular Structure, v. 1106, p. 291-299, 2016. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0022286015304014>. Acesso em: 26 set. 2016. 0022-2860 |
url |
http://www.repositorio.ufop.br/handle/123456789/7069 |
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.source.none.fl_str_mv |
reponame:Repositório Institucional da UFOP instname:Universidade Federal de Ouro Preto (UFOP) instacron:UFOP |
instname_str |
Universidade Federal de Ouro Preto (UFOP) |
instacron_str |
UFOP |
institution |
UFOP |
reponame_str |
Repositório Institucional da UFOP |
collection |
Repositório Institucional da UFOP |
bitstream.url.fl_str_mv |
http://www.repositorio.ufop.br/bitstream/123456789/7069/2/license.txt http://www.repositorio.ufop.br/bitstream/123456789/7069/1/ARTIGO_ConfomerismEnantiomorphismDouble.pdf |
bitstream.checksum.fl_str_mv |
62604f8d955274beb56c80ce1ee5dcae 342ec8f6cb11128190d79006d735b10a |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 |
repository.name.fl_str_mv |
Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP) |
repository.mail.fl_str_mv |
repositorio@ufop.edu.br |
_version_ |
1801685716456964096 |