Evaluation of the chemical reactivity in lignin precursors using the Fukui function.
The hydroxycinnamyl alcohols: p-coumarol, coniferol and sinapol are considered the basic units and precursors of lignins models. In this work, the specific reactivity of these molecules was studied. We investigate their intrinsic chemical reactivity in terms of the Fukui function, applying the principle of hard and soft acids and bases (HSAB) in the framework of the density functional theory (DFT). Comparisons of their nucleophilic, electrophilic and free radical reactivity show their most probably sites to form linkages among them. It is found that the most reactive sites, for reactions involving free radicals, are the carbons at the beta-position in the p-coumarol and sinapol molecules, whilst the regions around the carbon-oxygen bond of the phenoxyl group are the most reactive in coniferol.
Wood Technology and Engineering Department, Universidad Michoacana de San Nicolás de Hidalgo, Morelia, Michoacán 58000, México.
Carmen
C
Martinez
José L
JL
Rivera
Rafael
R
Herrera
José L
JL
Rico
Nelly
N
Flores
José G
JG
Rutiaga
Pablo
P
López
D008031:Lignin / Q000096:biosynthesis / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D020005:Propanols / Q000737:chemistry
D020005:Propanols; D008031:Lignin; C020722:cinnamyl alcohol