Twisted Imide Bond in Noncyclic Imides. Synthesis and Structural and Vibrational Properties of N,N-Bis(furan-2-carbonyl)-4-chloroaniline

Abstract

A novel imide compound (C(16)H(10)ClNO(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.

A novel 3-acetoxy-2-methyl-N-(4-methoxyphenyl)benzamide: Molecular structural describe, antioxidant activity with use X-ray diffractions and DFT calculations

“…The N1-C8 bond distance is observed at higher value with regard to C 16 H 10 ClNO 4 (1.413 Å) [39]. The molecular conformation in the crystal the C16-C17/O2/O4 plane forms a dihedral angle of 61.52 (6)° with the benzene ring (C9-C14) linked to C15 atom and O3/C8/N1 plane forming a dihedral angle (16)° with the benzene ring (C1-C7) linked to methoxy grup (C1/O1).…”

“…The crystal structure of the compound, crystallized in a triclinic space group P-1, with Z = [38,39]. The N1-C8 bond distance is observed at higher value with regard to C 16 H 10 ClNO 4 (1.413 Å) [39].…”

Experimental and theoretical insights into the formation of weak hydrogen bonds and H⋯H bonding interactions in the solid-state structure of two eucalyptol derivatives

“…As quantum chemical computations usually overestimate bond force constants, the use of a 0.9676 scale factor for the largest wavenumber values provides a better fit with the experimental figures. 55 A direct comparison of the vibrational spectra of compounds 4 and 6 with those obtained for parent eucalyptol and lately reported 9-hydroxyeucaliptol 20a strikes for the presence of bands of unexpected shape, ca. 3500-3400 cm À1 , a wellknown region characteristic of the O-H stretching fundamental mode of alcohols and phenols.…”

Novel ferrocene imide derivatives: synthesis, conformational analysis and X-ray structure

“…Due to favourable π-stacking and C−H∙∙∙π interactions between the ferrocenyl units and steric factors, cis - cis conformations are present both in the solid state and in solution of I and II , rather than an energetically favourable cis - trans conformations found in simple acyclic imides [ 13 , 14 ]. A twisted imide bond ( cis-cis ) was also reported in the crystal structure of the novel noncyclic imide derived from 4-chloroaniline and 2-furoic acid [ 15 ]. The nonplanarity of the imide group was related to the steric hindrances of the 2-carbonyl furan rings.…”