Modeling organochlorine compounds and the σ-hole effect using a polarizable multipole force field.

ABSTRACT: The charge distribution of halogen atoms on organochlorine compounds can be highly anisotropic and even display a so-called σ-hole, which leads to strong halogen bonds with electron donors. In this paper, we have systematically investigated a series of chloromethanes with one to four chloro substituents using a polarizable multipole-based molecular mechanics model. The atomic multipoles accurately reproduced the ab initio electrostatic potential around chloromethanes, including CCl4, which has a prominent σ-hole on the Cl atom. The van der Waals parameters for Cl were fitted to the experimental density and heat of vaporization. The calculated hydration free energy, solvent reaction fields, and interaction energies of several homo- and heterodimer of chloromethanes are in good agreement wit

SUBMITTER: Mu X 

PROVIDER: S-EPMC4065202 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature