title: An evaluation of the GLYCAM06 and MM3 force fields, and the PM3-D* molecular orbital method for modelling prototype carbohydrate-aromatic interactions.
abstract: 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.
authors.affiliation: School of Chemistry, University of Manchester, Oxford Road, Manchester M139PL, UK.
authors.forename: Anitha
authors.initials: A
authors.lastname: Ramraj
authors.forename: Rajesh K
authors.initials: RK
authors.lastname: Raju
authors.forename: Qiantao
authors.initials: Q
authors.lastname: Wang
authors.forename: Ian H
authors.initials: IH
authors.lastname: Hillier
authors.forename: Richard A
authors.initials: RA
authors.lastname: Bryce
authors.forename: Mark A
authors.initials: MA
authors.lastname: Vincent
mesh_terms: 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
chemical_list: D002241:Carbohydrates; D006841:Hydrocarbons, Aromatic; D007211:Indoles; D005643:Fucose; D014050:Toluene; D005947:Glucose