Evaluation of the Performance of GAFF and CGenFF in the Prediction of Liquid–Vapor Saturation Properties of Naphthalene Derivatives

Abstract

We examine the performance of the general AMBER force field (GAFF) and the CHARMM general force field (CGenFF) within the context of capturing the liquid–vapor saturation properties of naphthalene derivatives. Molecular simulation is employed to construct phase diagrams for naphthalene, tetralin, trans-decalin, quinolone, 1-methylnaphthalene, 1-naphthol, indole, benzo­[b]­furan, and benzo­[b]­thiophene over a range of temperatures that spans from room temperature to the critical point. A general histogram-based approach introduced by Rane and co-workers (J. Chem. Theory Comput. 2013, 9, 2552) is used to calculate saturated densities, vapor pressures, and enthalpies of vaporization. Results for GAFF and CGenFF are compared to experimental data, available correlations, and literature results for the transferable potentials for phase equilibria force field (TraPPE). GAFF and CGenFF provide reasonable descriptions for the saturation properties of the naphthalene derivatives studied. Specifically, GAFF and CGenFF capture the critical temperature to within average errors of 5.6 and 6.3%, respectively, and the boiling temperature to within average errors of 4.0 and 4.4%, respectively. The models generally produce estimates of the critical temperature and boiling temperature that are low relative to experiment. The two models provide a relatively consistent description of the six molecules studied containing two fused six-membered rings, whereas their description of the three molecules examined containing fused five- and six-membered rings often differs appreciably. In terms of an overall comparison, our results do not indicate that one force field clearly outperforms the other.

Calculation of the Saturation Properties of a Model Octane–Water System Using Monte Carlo Simulation

“…However, it is computationally expensive to conduct direct simulations at each state point of interest. In previous studies, ,,− our group introduced a means for efficiently tracing the evolution of a saturation curve over a path of interest (e.g., temperature, pressure, and activity fraction). In what follows, we first describe the general approach and then provide specific examples.…”

Evaluating the Performance of Water Models with Host–Guest Force Fields in Binding Enthalpy Calculations for Cucurbit[7]uril–Guest Systems

“…The CGenFF server produces default host parameters, which clearly require further optimization, at least in our hands. Both GAFFv1 and CGenFF can provide reasonable force fields for reproducing experimental data even though CGenFF performs worse overall in the binding enthalpy calculations. , …”

“…Both GAFFv1 and CGenFF can provide reasonable force fields for reproducing experimental data even though CGenFF performs worse overall in the binding enthalpy calculations. [73][74] In this assessment, it is also important to consider the uncertainties associated with both the experimental and computational values. The reported experimental uncertainties of the mean range between 0.01 and 2.31 kcal/mol and most of them are lower than 0.50 kcal/mol.…”

Computational Insights into the Aggregation Pathway of Self-Assembled Nanotubules

“…The force field parameters of the amphiphile were generated using the CHARMM General Force Field (CGenFF) − available on the ParamChem Web site . CGenFF is reported to show good performance in the simulation of small organic molecules among the widely used force fields. , The corresponding penalty score data are given in Table S2.…”

“…66 CGenFF is reported to show good performance in the simulation of small organic molecules among the widely used force fields. 67,68 The corresponding penalty score data are given in Table S2.…”