Synthesis of Dichlorobenzamide Derivatives: Crystal Structures of 3,5-Dichloro-N-(2-chlorophenyl)benzamide and 3,5-Dichloro-N-(4-chlorophenyl)benzamide

Zhang, Jun; Li, Yue; Wang, Bei; Jia, Ai‐Quan; Zhang, Qian‐Feng

doi:10.1007/s10870-020-00822-9

Cited by 1 publication

(2 citation statements)

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“…Analysis of a benzamide search [C 13 H 8 X 3 O 1 N 1 formula; X = F, Cl, Br, I and C 6 CONHC 6 skeleton] and reviewing various trihalide (X) combinations shows that the majority are chloroderivatives. The chloro-derivatives provide ten CSD structural 'hits' and structures, as listed by CANYAV, CANYEZ [3,22], ENUKAA [23], JOFHAO [24], KODTUT [25], LAQ-DOY [26], XEHZOD [20], YODDUR [27], YOVMIG [28] and ZAJWUF [21].…”

Section: Overall Structural Results and Related Literaturementioning

confidence: 99%

“…The benzamide crystal structures reported in the Cambridge Structural Database [3] facilitate analysis of physicochemical research trends and patterns. Ongoing research is directed towards the development of larger n × m benzamide isomer grids and correlating properties such as melting points, spectroscopic and structural data [3][4][5][6][7][8][9][10][20][21][22][23][24][25][26][27][28]. Even when analyzing relatively small molecules such as benzamides, there are gaps in our structural knowledge where crystal structure prediction can potentially be used to fill the spaces [29].…”

Section: Discussionmentioning

confidence: 99%

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N-(2,4-Difluorophenyl)-2-fluorobenzamide

Hehir,

Gallagher

2024

Molbank

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The title compound N-(2,4-difluorophenyl)-2-fluorobenzamide (Fo24) was synthesized in high yield (1.09 g; 87%) using standard synthetic procedures from the condensation reaction of 2-fluorobenzoyl chloride with 2,4-difluoroaniline. Crystals of Fo24 were grown from CH2Cl2 at room temperature. The Fo24 crystal structure was determined using single-crystal X-ray diffraction methods at 294 (1) K in space group Pn (No. 7). Fo24 is the second regular tri-fluorinated benzamide with the formula C13H8F3N1O1 to be reported and contrasts with the more common difluorinated and tetra-fluorinated analogues. In Fo24, both aromatic rings are effectively coplanar with an interplanar angle of 0.7(2)°. The central amide group plane is oriented by 23.04(18)° and 23.69(17)° from both aromatic rings, forming an intramolecular contact with an ortho-F12 atom with H1⋯F12 = 2.12(4) Å. The primary hydrogen bonds are 1D amide–amide interactions that form along the b-axis direction. In addition, weaker C-H⋯F/O interactions are noted: a R22(12) synthon involving two C-H, a N-H and two C-F groups, with C-F⋯C ring–ring stacking contacts completing the interactions.

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