ci300095x_si_001.pdf (434.66 kB)
Predicting the Sites and Energies of Noncovalent Intermolecular Interactions Using Local Properties
journal contribution
posted on 2012-04-23, 00:00 authored by Ahmed El Kerdawy, Christian
R. Wick, Matthias Hennemann, Timothy ClarkFeed-forward artificial neural nets have been used to
recognize H-bond donor and acceptor sites on drug-like molecules based
on local properties (electron density, molecular electrostatic potential
and local ionization energy, electron affinity, and polarizability)
calculated at grid points around the molecule. Interaction energies
for training were obtained from B97-D and ωB97X-D/aug-cc-pVDZ
density-functional theory calculations on a series of model central
molecules and H-bond acceptor and donor probes constrained to the
grid points used for training. The resulting models provide maps of
both classical and unusual H- and halogen-bonding sites. Note that
these reactions result even though only classical H-bond donors and
acceptors were used as probes around the central molecules. Some examples
demonstrate the ability of the models to take the electronics of the
central molecule into consideration and to provide semiquantitative
estimates of interaction energies at low computational cost.