International Journal of Applied Science and Engineering Research
  • Year: 2013
  • Volume: 2
  • Issue: 2

N-H…O hydrogen bonding and π-π interactions in 2-Amino-1- (4-methoxy-phenyl)-5-oxo-4,5-dihydro-1H-pyrrole-3- carboxylic acid ethyl ester

1Department of Physics, Sardar Patel University, Vallabh, Vidyanagar-388120, Gujarat, India

2Natubhai V. Patel College of Pure and Applied Sciences, Vallabh, Vidyanagar-388120, Gujarat, India

3Organic Synthesis Laboratory, M. G. Science Institute, Ahmedabad, Gujarat, India

*Corresponding author e-mail: fbdpatel@gmail.com

Online published on 11 September, 2014.

Abstract

The pyrrole derivatives show a broad spectrum of biological activities such as anticancer, antidiabetic, aldose reductase inhibition, anti-inflammatory and analgesic activities and therefore these derivatives attracted much attention. The title compound, 2-Amino-1-(4-methoxy-phenyl)-5-oxo-4,5- dihydro-1H-pyrrole-3-carboxylic acid ethyl ester, C14H16N2O4, a novel Pyrrole derivative has been synthesized and characterized by NMR. The crystal structure of it is determined using X-ray crystallographic technique. It crystallizes in to monoclinic space group P21/n with lattice parameters a = 4.088, b = 27.696, c = 11.763 Å and β = 93.76(0)°. In the title compound, the pyrrole ring is planar. The configuration of the substituted ethoxy carbonyl moiety is an extended zigzag chain lying parallel along b-axis. N-H…O (intra) and N-H…O (inter) interactions along with C-H…O interactions form a ring and chain of (14) graph-set motifs respectively. Another C-H…O interactions interlinked the rings forming molecular chain along [001] direction. An off-centric π-π interaction involving pyrrole ring and symmetry related phenyl ring of the superimposed molecular chain responsible for the stability of the molecule along [100] direction.

Keywords

Pyrrole, Molecular interactions, Graph set motifs, Symmetry