Crystal structure of 2,5-dimethyl-1-(4-carboxyphenyl)pyrrole, C13H13NO2

Abstract

C 13 H 13 NO 2 ,orthorhombic, Pbcn (no. 60), a =12.4741(2) Å, b =11.1481(2) Å, c =16. Source of materialTo asolutionofthe 4-aminobenzoic acid (1 mmol)and 2,5-hexadione (1.2 mmol) in THF (10 mL) at room temperature was added iodine (0.1 mmol). The mixture was stirred at this temperature with an N 2 positiveflow for aperiod of 2hours. Dichloromethane (20 mL) was then added to the mixture. The resulting mixture was washed successively with 5%N a 2 S 2 O 3solution (2 mL), saturated NaHCO3 solution (2 mL), and brine (2 mL). The organic layerwas then dried with sodium sulfate and concentrated. The product obtained was then purifiedbyflash chromatography with dichoromethane as novel phase and after completeevaporation of the solvent, 0.611 gof4-(2,5-dimethyl-pyrrol-1-yl)-benzoic acid were obtained. The compoundwas recrystallized from dichloromethane. Experimental detailsThe atomic coordinates of the carboxylic Hatom were freely refined and two alternative positions were allowed for this atom, either closer to O1 either closer to O2. The occupancy of each site refined to near 50 %.

2,2′,5,5′-Tetramethyl-1,1′-(hexane-1,6-diyl)di-1H-pyrrole

“…For the use of chain spacers in conductive polymers, see: Zotti et al (1997); Chane-Ching et al (1998); Just et al (1999). For related structures, see: Ramos Silva et al (2002Silva et al ( , 2005Silva et al ( , 2008.…”

“…Within our project of synthesizing new pyrrole derivatives for several technological purposes (Ramos Silva et al, 2002;Ramos Silva et al, 2005;Ramos Silva et al, 2008), we have prepared the title compound. This pyrrole derivative contains a long alkyl chain between two pyrrole rings.…”