An evaluation of the GLYCAM06 and MM3 force fields, and the PM3-D* molecular orbital method for modelling prototype carbohydrate-aromatic interactions.
The structures and interaction energies of 21 binary complexes of fucose and glucose with toluene, 3-methylindole or p-hydroxytoluene, evaluated at the DFT-D level, are used to judge the accuracy of the GLYCAM06 and MM3 force fields, and the PM3-D* molecular orbital method for modelling carbohydrate-arene interactions. The accuracy of the DFT-D method is substantiated by comparison with high level CCSD(T) calculations on a small number of representative complexes. It is found that a correct description of the intermolecular dispersive interactions is essential. Both the PM3-D* method and the GYLCAM06 force field yield interaction energies within 1 kcal mol⁻¹ of the DFT-D values, whilst those from the MM3 force field are in error by more than 2 kcal mol⁻¹.
Ramraj
Anitha
A
School of Chemistry, University of Manchester, Oxford Road, Manchester M139PL, UK.
Raju
Rajesh K
RK
Wang
Qiantao
Q
Hillier
Ian H
IH
Bryce
Richard A
RA
Vincent
Mark A
MA
D002241:Carbohydrates / Q000737:chemistry*; D003198:Computer Simulation; D005643:Fucose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D008958:Models, Molecular; D014050:Toluene / Q000737:chemistry
D002241:Carbohydrates; D006841:Hydrocarbons, Aromatic; D007211:Indoles; D005643:Fucose; D014050:Toluene; D005947:Glucose