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Density functional theory methods are utilized to investigate structural features and stabilities of the most common lignin dimerization products. It is found that intra-molecular hydrogen bonding acts as a stabilizing force in the lowest-energy conformer(s) of several different dimeric lignin structures. Furthermore, the calculations show that the hypothesis of thermodynamic control of monolignol dimerization accounts for some of the results obtained in experimental studies aimed at determining the ratios of intermonomeric linkages. A quantitative correlation between experimentally observed ratios and calculated relative energies cannot, however, be pointed out.

holzforschung

A Density Functional Theory Study of Coniferyl Alcohol Intermonomeric Cross Linkages in Lignin -  Three-Dimensional Structures, Stabilities and the Thermodynamic Control Hypothesis