2,4-Diarylpyrroles: synthesis, characterization and crystallographic insights.
Acta Crystallogr C Struct Chem
; 2024 Sep 01.
Article
in En
| MEDLINE
| ID: mdl-39115536
ABSTRACT
Three 2,4-diarylpyrroles were synthesized starting from 4-nitrobutanones and the crystal structures of two derivatives were analysed. These are 4-(4-methoxyphenyl)-2-(thiophen-2-yl)-1H-pyrrole, C15H13NOS, and 3-(4-bromophenyl)-2-nitroso-5-phenyl-1H-pyrrole, C16H11BrN2O. Although pyrroles without substituents at the α-position with respect to the N atom are very air sensitive and tend to polymerize, we succeeded in growing an adequate crystal for X-ray diffraction analysis. Further derivatization using sodium nitrite afforded a nitrosyl pyrrole derivative, which crystallized in the triclinic space group P\overline{1} with Z = 6. Thus, herein we report the first crystal structure of a nitrosyl pyrrole. Interestingly, the co-operative hydrogen bonds in this NO-substituted pyrrole lead to a trimeric structure with bifurcated halogen bonds at the ends, forming a two-dimensional (2D) layer with interstitial voids having a radius of 5â
Å, similar to some reported macrocyclic porphyrins.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Acta Crystallogr C Struct Chem
Year:
2024
Document type:
Article
Affiliation country:
Mexico