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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/82276
Ver los metadatos del registro completo
id |
CONICETDig_b46c925ca52d0456dc3e28eb4616fb7a |
---|---|
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 Técnicas2025-09-29T10:45:33Zoai: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:34982025-09-29 10:45:33.39CONICET 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_ |
1844614495405604864 |
score |
13.070432 |