Artículo
Twisted imide bond in noncyclic imides. Synthesis and structural and vibrational properties of N, N -bis(furan-2-carbonyl)-4-chloroaniline
Fecha de publicación:
05/2012
Editorial:
American Chemical Society
Revista:
Journal of Organic Chemistry
ISSN:
0022-3263
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
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.
Palabras clave:
Imides
,
Conformation
,
Structure
,
Spectroscopy
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Identificadores
Colecciones
Articulos(CEQUINOR)
Articulos de CENTRO DE QUIMICA INORGANICA "DR. PEDRO J. AYMONINO"
Articulos de CENTRO DE QUIMICA INORGANICA "DR. PEDRO J. AYMONINO"
Citación
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
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