A conceptual DFT study of the molecular properties of glycating carbonyl compounds

Several glycating carbonyl compounds have been studied by resorting to the latest Minnesota family of density functional with the objective of determinating their molecular properties. In particular, the chemical reactivity descriptors that arise from conceptual density functional theory and chemical reactivity theory have been calculated through a \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$\Delta$$\end{document}ΔSCF protocol. The validity of the KID (Koopmans’ in DFT) procedure has been checked by comparing the reactivity descriptors obtained from the values of the HOMO and LUMO with those calculated through vertical energy values. The reactivity sites have been determined by means of the calculation of the Fukui function indices, the condensed dual descriptor \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$\Delta {f}(\mathbf {r})$$\end{document}Δf(r) and the electrophilic and nucleophilic Parr functions. The glycating power of the studied compounds have been compared with the same property for simple carbohydrates.Graphical abstract Several glycating carbonyl compounds have been studied by resorting to the latest Minnesota family of density functional with the objective of determinating their molecular properties, the chemical reactivity descriptors and the validity of the KID (Koopmans’ in DFT) procedure Electronic supplementary material The online version of this article (doi:10.1186/s13065-017-0239-7) contains supplementary material, which is available to authorized users.

: HOMO and LUMO orbital energies (in eV), ionization potentials I and electron affinities A (in eV), and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power (ω − ), electroaccepting power (ω + ), and net electrophilicity ∆ω ± of Acetaldehyde, Acetol, Acetone, Arabinose, Glucose, d-Glyceraldehyde, Glyoxal, l-Glyceraldehyde, Methylglyoxal and Ribose calculated with the M11 density functional and the Def2TZVP basis set using water as solvent simulated with the SMD parametrization of the IEF-PCM model. The upper part of the table shows the results derived assuming the validity of KID procedure and the lower part shows the results derived from the calculated vertical I and A.
Property  Table S2A: HOMO and LUMO orbital energies (in eV), ionization potentials I and electron affinities A (in eV), and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power (ω − ), electroaccepting power (ω + ), and net electrophilicity ∆ω ± of Acetaldehyde, Acetol, Acetone, Arabinose, Glucose, d-Glyceraldehyde, Glyoxal, l-Glyceraldehyde, Methylglyoxal and Ribose calculated with the M11L density functional and the Def2TZVP basis set using water as solvent simulated with the SMD parametrization of the IEF-PCM model. The upper part of the table shows the results derived assuming the validity of KID procedure and the lower part shows the results derived from the calculated vertical I and A.
Property   Table S3A: HOMO and LUMO orbital energies (in eV), ionization potentials I and electron affinities A (in eV), and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power (ω − ), electroaccepting power (ω + ), and net electrophilicity ∆ω ± of Acetaldehyde, Acetol, Acetone, Arabinose, Glucose, d-Glyceraldehyde, Glyoxal, l-Glyceraldehyde, Methylglyoxal and Ribose calculated with the MN12L density functional and the Def2TZVP basis set using water as solvent simulated with the SMD parametrization of the IEF-PCM model. The upper part of the table shows the results derived assuming the validity of KID procedure and the lower part shows the results derived from the calculated vertical I and A.
Property   Table S4A: HOMO and LUMO orbital energies (in eV), ionization potentials I and electron affinities A (in eV), and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power (ω − ), electroaccepting power (ω + ), and net electrophilicity ∆ω ± of Acetaldehyde, Acetol, Acetone, Arabinose, Glucose, d-Glyceraldehyde, Glyoxal, l-Glyceraldehyde, Methylglyoxal and Ribose calculated with the MN12SX density functional and the Def2TZVP basis set using water as solvent simulated with the SMD parametrization of the IEF-PCM model. The upper part of the table shows the results derived assuming the validity of KID procedure and the lower part shows the results derived from the calculated vertical I and A.
Property   Table S5A: HOMO and LUMO orbital energies (in eV), ionization potentials I and electron affinities A (in eV), and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power (ω − ), electroaccepting power (ω + ), and net electrophilicity ∆ω ± of Acetaldehyde, Acetol, Acetone, Arabinose, Glucose, d-Glyceraldehyde, Glyoxal, l-Glyceraldehyde, Methylglyoxal and Ribose calculated with the N12 density functional and the Def2TZVP basis set using water as solvent simulated with the SMD parametrization of the IEF-PCM model. The upper part of the table shows the results derived assuming the validity of KID procedure and the lower part shows the results derived from the calculated vertical I and A.
Property   Table S6A: HOMO and LUMO orbital energies (in eV), ionization potentials I and electron affinities A (in eV), and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power (ω − ), electroaccepting power (ω + ), and net electrophilicity ∆ω ± of Acetaldehyde, Acetol, Acetone, Arabinose, Glucose, d-Glyceraldehyde, Glyoxal, l-Glyceraldehyde, Methylglyoxal and Ribose calculated with the N12SX density functional and the Def2TZVP basis set using water as solvent simulated with the SMD parametrization of the IEF-PCM model. The upper part of the table shows the results derived assuming the validity of KID procedure and the lower part shows the results derived from the calculated vertical I and A.

Property
HOMO  Table S7A: HOMO and LUMO orbital energies (in eV), ionization potentials I and electron affinities A (in eV), and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power (ω − ), electroaccepting power (ω + ), and net electrophilicity ∆ω ± of Acetaldehyde, Acetol, Acetone, Arabinose, Glucose, d-Glyceraldehyde, Glyoxal, l-Glyceraldehyde, Methylglyoxal and Ribose calculated with the SOGGA11 density functional and the Def2TZVP basis set using water as solvent simulated with the SMD parametrization of the IEF-PCM model. The upper part of the table shows the results derived assuming the validity of KID procedure and the lower part shows the results derived from the calculated vertical I and A.
Property  Table S8A: HOMO and LUMO orbital energies (in eV), ionization potentials I and electron affinities A (in eV), and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power (ω − ), electroaccepting power (ω + ), and net electrophilicity ∆ω ± of Acetaldehyde, Acetol, Acetone, Arabinose, Glucose, d-Glyceraldehyde, Glyoxal, l-Glyceraldehyde, Methylglyoxal and Ribose calculated with the SOGGA11X density functional and the Def2TZVP basis set using water as solvent simulated with the SMD parametrization of the IEF-PCM model. The upper part of the