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Twisted Imide Bond in Noncyclic Imides. Synthesis and Structural and Vibrational Properties of N,N-Bis(furan-2-carbonyl)-4-chloroaniline
- Source :
- The Journal of Organic Chemistry. 77:4688-4695
- Publication Year :
- 2012
- Publisher :
- American Chemical Society (ACS), 2012.
-
Abstract
- 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
- Subjects :
- STRUCTURE
SPECTROSCOPY
Stereochemistry
Organic Chemistry
Ciencias Químicas
Dihedral angle
Planarity testing
CONFORMATION
Crystallography
chemistry.chemical_compound
Química Orgánica
chemistry
Furan
Moiety
Imide
Carbonyldiimidazole
IMIDES
CIENCIAS NATURALES Y EXACTAS
Natural bond orbital
Monoclinic crystal system
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 77
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....537fd7e57194f6b7919d616c5826b16f