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Issue 47, 2011
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Evaluation of potential reaction mechanisms leading to the formation of coniferyl alcohol α-linkages in lignin: a density functional theory study

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Abstract

Five potential reaction mechanisms, each leading to the formation of an α-O-4-linked coniferyl alcohol dimer, and one scheme leading to the formation of a recently proposed free-radical coniferyl alcohol trimer were assessed using density functional theory (DFT) calculations. These potential reaction mechanisms were evaluated using both the calculated Gibbs free energies, to predict the spontaneity of the constituent reactions, and the electron-density mapped Fukui function, to determine the most reactive sites of each intermediate species. The results indicate that each reaction in one of the six mechanisms is thermodynamically favorable to those in the other mechanisms; what is more, the Fukui function for each free radical intermediate corroborates with the thermochemical results for this mechanism. This mechanism proceeds via the formation of two distinct free-radical intermediates, which then react to produce the four α-O-4 stereoisomers.

Graphical abstract: Evaluation of potential reaction mechanisms leading to the formation of coniferyl alcohol α-linkages in lignin: a density functional theory study

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Publication details

The article was received on 10 Jun 2011, accepted on 27 Sep 2011 and first published on 18 Oct 2011


Article type: Paper
DOI: 10.1039/C1CP21906E
Citation: Phys. Chem. Chem. Phys., 2011,13, 20974-20985
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    Evaluation of potential reaction mechanisms leading to the formation of coniferyl alcohol α-linkages in lignin: a density functional theory study

    H. D. Watts, M. N. A. Mohamed and J. D. Kubicki, Phys. Chem. Chem. Phys., 2011, 13, 20974
    DOI: 10.1039/C1CP21906E

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