Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline

Autores
Saeed, Aamer; Erben, Mauricio Federico; Bolte, Michael
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel imide compound (C 16H 10ClNO 4) was synthesized in a single step by the reaction of 2-furoic acid with 4-chloroaniline in a 2:1 molar ratio using carbonyldiimidazole (CDI) in dry THF. The structure was supported by spectroscopic and elemental analyses and the single-crystal X-ray diffraction data. Crystallographic studies revealed that the compound crystallized in a monoclinic system with space group P2 1/c and unit cell dimensions a = 12.2575(5) Å, b = 7.7596(2) Å, c = 15.0234(7) Å, α = γ = 90°, β = 92.771(4)°, V = 1427.25(10) Å 3, Z = 4. The imide bond is twisted, and the O=C-N-C(O) units deviate significantly from planarity with dihedral angles around the imide group reaching ca. -150.3° (C1-N1-C2-O21 = -148.8° and C2-N1-C1-O11 = -151.9°). The nonplanarity of the imide moiety and the related conformational properties are discussed in a combined approach that includes the analysis of the vibrational spectra together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) calculations.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Bolte, Michael. Goethe Universitat Frankfurt; Alemania
Materia
Imides
Conformation
Structure
Spectroscopy
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/82276
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/82276
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroanilineSaeed, AamerErben, Mauricio FedericoBolte, MichaelImidesConformationStructureSpectroscopyhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel imide compound (C 16H 10ClNO 4) was synthesized in a single step by the reaction of 2-furoic acid with 4-chloroaniline in a 2:1 molar ratio using carbonyldiimidazole (CDI) in dry THF. The structure was supported by spectroscopic and elemental analyses and the single-crystal X-ray diffraction data. Crystallographic studies revealed that the compound crystallized in a monoclinic system with space group P2 1/c and unit cell dimensions a = 12.2575(5) Å, b = 7.7596(2) Å, c = 15.0234(7) Å, α = γ = 90°, β = 92.771(4)°, V = 1427.25(10) Å 3, Z = 4. The imide bond is twisted, and the O=C-N-C(O) units deviate significantly from planarity with dihedral angles around the imide group reaching ca. -150.3° (C1-N1-C2-O21 = -148.8° and C2-N1-C1-O11 = -151.9°). The nonplanarity of the imide moiety and the related conformational properties are discussed in a combined approach that includes the analysis of the vibrational spectra together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) calculations.Fil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Bolte, Michael. Goethe Universitat Frankfurt; AlemaniaAmerican Chemical Society2012-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/82276Saeed, Aamer; Erben, Mauricio Federico; Bolte, Michael; Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline; American Chemical Society; Journal of Organic Chemistry; 77; 10; 5-2012; 4688-46950022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jo300360binfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo300360binfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:44:03Zoai:ri.conicet.gov.ar:11336/82276instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 15:44:03.361CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
title Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
spellingShingle Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
Saeed, Aamer
Imides
Conformation
Structure
Spectroscopy
title_short Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
title_full Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
title_fullStr Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
title_full_unstemmed Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
title_sort Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
dc.creator.none.fl_str_mv Saeed, Aamer
Erben, Mauricio Federico
Bolte, Michael
author Saeed, Aamer
author_facet Saeed, Aamer
Erben, Mauricio Federico
Bolte, Michael
author_role author
author2 Erben, Mauricio Federico
Bolte, Michael
author2_role author
author
dc.subject.none.fl_str_mv Imides
Conformation
Structure
Spectroscopy
topic Imides
Conformation
Structure
Spectroscopy
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A novel imide compound (C 16H 10ClNO 4) was synthesized in a single step by the reaction of 2-furoic acid with 4-chloroaniline in a 2:1 molar ratio using carbonyldiimidazole (CDI) in dry THF. The structure was supported by spectroscopic and elemental analyses and the single-crystal X-ray diffraction data. Crystallographic studies revealed that the compound crystallized in a monoclinic system with space group P2 1/c and unit cell dimensions a = 12.2575(5) Å, b = 7.7596(2) Å, c = 15.0234(7) Å, α = γ = 90°, β = 92.771(4)°, V = 1427.25(10) Å 3, Z = 4. The imide bond is twisted, and the O=C-N-C(O) units deviate significantly from planarity with dihedral angles around the imide group reaching ca. -150.3° (C1-N1-C2-O21 = -148.8° and C2-N1-C1-O11 = -151.9°). The nonplanarity of the imide moiety and the related conformational properties are discussed in a combined approach that includes the analysis of the vibrational spectra together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) calculations.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Bolte, Michael. Goethe Universitat Frankfurt; Alemania
description A novel imide compound (C 16H 10ClNO 4) was synthesized in a single step by the reaction of 2-furoic acid with 4-chloroaniline in a 2:1 molar ratio using carbonyldiimidazole (CDI) in dry THF. The structure was supported by spectroscopic and elemental analyses and the single-crystal X-ray diffraction data. Crystallographic studies revealed that the compound crystallized in a monoclinic system with space group P2 1/c and unit cell dimensions a = 12.2575(5) Å, b = 7.7596(2) Å, c = 15.0234(7) Å, α = γ = 90°, β = 92.771(4)°, V = 1427.25(10) Å 3, Z = 4. The imide bond is twisted, and the O=C-N-C(O) units deviate significantly from planarity with dihedral angles around the imide group reaching ca. -150.3° (C1-N1-C2-O21 = -148.8° and C2-N1-C1-O11 = -151.9°). The nonplanarity of the imide moiety and the related conformational properties are discussed in a combined approach that includes the analysis of the vibrational spectra together with theoretical calculation methods, especially in terms of natural bond orbital (NBO) calculations.
publishDate 2012
dc.date.none.fl_str_mv 2012-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/82276
Saeed, Aamer; Erben, Mauricio Federico; Bolte, Michael; Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline; American Chemical Society; Journal of Organic Chemistry; 77; 10; 5-2012; 4688-4695
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/82276
identifier_str_mv Saeed, Aamer; Erben, Mauricio Federico; Bolte, Michael; Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline; American Chemical Society; Journal of Organic Chemistry; 77; 10; 5-2012; 4688-4695
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jo300360b
info:eu-repo/semantics/altIdentifier/doi/10.1021/jo300360b
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1846083544207589376
score 13.22299

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