The 1H and 13C chemical shifts of 55 lignin model dimers: An evaluation of DFT functionals

被引：0

作者：

Nguyen, Thien T. ^{[1
,2
]}

Le, Phong Q. ^{[3
]}

Helminen, Jussi ^{[4
]}

Sipilä, Jussi ^{[4
]}

机构：

[1] Institute of Research and Development, Duy Tan University, Da Nang,550000, Viet Nam

[2] Faculty of Natural Science, Duy Tan University, Da Nang,550000, Viet Nam

[3] School of Biotechnology, International University, Vietnam National University, Ho Chi Minh City,700000, Viet Nam

[4] Department of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, Helsinki FI,00014, Finland

来源：

Journal of Molecular Structure | 2022年 / 1226卷

关键词：

Dimers - Lignin - Quantum chemistry;

D O I：

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学科分类号：

摘要：

The calculations of 1H and 13C NMR chemical shifts were performed on three 55 lignin dimers, prominent substructures in softwood lignins, to compare with experimental data. Initially, 10 DFT functionals (B3LYP, B3PW91, BPV86, CAM-B3LYP, HCTH, HSEH1PBE, mPW1PW91, PBEPBE, TPSSTPSS, and ωB97XD) combined with the gage-including atomic orbital (GIAO) method and basic set 631G(d,p) were tested on 3,3-(6,6-dihydroxy-5,5-dimethoxy-[1,1-biphenyl]-3,3-diyl)dipropionic acid (1), efficiently synthesized from ferulic acid. HSEH1PBE, mPW1PW91, and ωB97XD were found to be the three best performing functionals with strong correlations (r2 ≥ 0.9988) and low errors (CMAEs ≤ 0.0611 ppm for 1H and CMAEs ≤ 1.19 ppm for 13C). These functionals were also well-performed for the 1H and 13C shift calculations of dimers 3,3-dimethoxy-5,5-dimethyl-[1,1-biphenyl]-2,2-diol (2) and 5,5-diallyl-3,3-dimethoxy-[1,1-biphenyl]-2,2-diol (3). Overall, the ωB97XD functional consistently provided the calculated 1H and 13C chemical shifts with a high level of accuracy. © 2020 Elsevier B.V.

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