Charge density and electrostatic potential analyses in paracetamol

Nouzha Bouhmaida (1) , François Bonhomme (2) , Benoît Guillot (3) , Christian Jelsch (3) , Nour Eddine Ghermani (4)

1 Mat Sci Lab
2 GPIA - Génome, populations, interactions, adaptation
3 CRM2 - Cristallographie, Résonance Magnétique et Modélisations
4 SPMS - Laboratoire Structures, Propriétés et Modélisation des solides

The electron density of monoclinic paracetamol was derived from high-resolution X-ray diffraction at 100 K. The Hansen– Coppens multipole model was used to refine the experimental electron density. The topologies of the electron density and the electrostatic potential were carefully analyzed. Numerical and analytical procedures were used to derive the charges integrated over the atomic basins. The highest charge magnitude (À1.2 e) was found for the N atom of the paracetamol molecule, which is in agreement with the observed nucleophilic attack occurring in the biological media. The electric field generated by the paracetamol molecule was used to calculate the atomic charges using the divergence theorem. This was simultaneously applied to estimate the total electrostatic force exerted on each atom of the molecule by using the Maxwell stress tensor. The interaction electrostatic energy of dimers of paracetamol in the crystal lattice was also estimated.

Domaines: Chimie; Cristallographie

Nouzha Bouhmaida, François Bonhomme, Benoît Guillot, Christian Jelsch, Nour Eddine Ghermani. Charge density and electrostatic potential analyses in paracetamol. Acta Crystallographica Section B : Structural Science [1968-2013], 2009, 65 (3), pp.363 - 374. ⟨10.1107/S0108768109008271⟩. ⟨hal-01713020⟩