Jump to main content
Jump to site search

Issue 17, 2013
Previous Article Next Article

Prediction of 1-octanol–water and air–water partition coefficients for nitro-aromatic compounds from molecular dynamics simulations

Author affiliations

Abstract

United-atom force fields, based on the Transferable Potentials for Phase Equilibria (TraPPE), are developed for twelve nitro-aromatic compounds, which include 2,4-dinitrotoluene (2,4-DNT), 2,6-dinitrotoluene (2,6-DNT), 3-nitrotoluene (3-NT), 4-nitrotoluene (4-NT), 1,3-dinitrobenzene (1,3-DNB), 1,4-dinitrobenzene (1,4-DNB), 2,4-dinitroanisole (DNAN), 1,3,5-trinitrobenzene (TNB), 2,4,6-trinitrotoluene (TNT), 2-nitroanisole (2-NAN), 4-nitroanisole (4-NAN) and n-methyl-p-nitroaniline (MNA). 1-Octanol–water and air–water partition coefficients are predicted for the optimized TraPPE-UA force field with adaptive biasing force molecular dynamics simulations, and compared to available experimental data. Log Kow values are predicted with an average absolute deviation of 0.2 log units, while Henry's law constants are predicted to with an average absolute deviation of 0.5 log units. Two additional models are presented for energetic materials with five membered rings for which no experimental data are available in the open literature: 3,5-dinitropyrazole (DNP) and 3-nitro-1,2,4-triazole-5-one (NTO). Investigation of the local microstructure around each solute reveals that 1-octanol is able to form hydrogen bonded chains around the solute, while little organized microstructure was observed around the solutes in water.

Graphical abstract: Prediction of 1-octanol–water and air–water partition coefficients for nitro-aromatic compounds from molecular dynamics simulations

Back to tab navigation

Supplementary files

Publication details

The article was received on 29 Nov 2012, accepted on 15 Mar 2013 and first published on 18 Mar 2013


Article type: Paper
DOI: 10.1039/C3CP44284E
Citation: Phys. Chem. Chem. Phys., 2013,15, 6467-6474
  •   Request permissions

    Prediction of 1-octanol–water and air–water partition coefficients for nitro-aromatic compounds from molecular dynamics simulations

    N. Bhatnagar, G. Kamath and J. J. Potoff, Phys. Chem. Chem. Phys., 2013, 15, 6467
    DOI: 10.1039/C3CP44284E

Search articles by author

Spotlight

Advertisements