title: Multi-way analysis of quantum topological molecular similarity descriptors for modeling acidity constant of some phenolic compounds.
abstract: Three-way analyses of quantum topological molecular similarity descriptors were used for quantitative structure property relationship modeling of the acidity constant of some phenol derivatives. A three-way data was built for different molecules by constructing a data matrix for each molecule. The matrix was produced by considering different bonds in each molecule and different descriptors in each bond. The three-way models parallel factor analysis and N-way partial least squares, and two-way models including partial least squares were used for modeling structure-acidity relationships. Comparison of the results showed that the three-way arrays produced more predictive models with lower over-fitting. The bilinear partial least square model resulted in a biased estimation of acidity constant of prediction set with average relative error of prediction of 1.87%, whereas that obtained by parallel factor analysis and N-way partial least squares was near to zero (i.e. -0.41 and -0.33, respectively). Additionally, the three-way methods allowed investigating the significant impact of different bonds and different descriptors using leverages of the parallel factor analysis loadings.
authors.affiliation: Department of Chemistry, Isfahan University of Technology, Isfahan 84154, Iran.
authors.forename: Mahnaz
authors.initials: M
authors.lastname: Esteki
authors.forename: Bahram
authors.initials: B
authors.lastname: Hemmateenejad
authors.forename: Taghi
authors.initials: T
authors.lastname: Khayamian
authors.forename: Afshan
authors.initials: A
authors.lastname: Mohajeri
mesh_terms: D002138:Calibration; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry*; D011789:Quantum Theory; D013329:Structure-Activity Relationship
chemical_list: D010636:Phenols