Abstract
Using IR Fourier transform spectroscopy we consider biosynthetic lignin models, namely, dehydropolymers. Quantum chemical calculations of IR spectra of model lignin structures were carried out within the framework of the density functional theory with the B3LYP functional in the 6-31+G(d,p) basis. The IR spectrum of a dimer with the C(8)—O—C(4) fragment describes well the specific features of the spectrum of the dehydropolymer synthesized from coniferyl alcohol. The presence of dimeric structures with double bonds in aliphatic chains and ether bonds between aromatic rings was determined in dehydropolymers from ferulic acid. The results of theoretical and experimental studies were shown to be in agreement with each other.
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References
S. Y. Lin, C. W. Dence, Methods in Lignin Chemistry, Springer-Verlag, Berlin, 1992, 578 pp.
A. P. Karmanov, M. F. Borisenkov, L. S. Kocheva, Chem. Nat. Compd., 2014, 50, 702.
J. L. Koenig, Spectroscopy of Polymers, Elsevier Science Inc., New-York, 1999, 491 pp.
K. V. Sarkanen, H. M. Chang, G. G. Allan, Tappi J., 1967, 50, 587.
A. P. Karmanov, O. Yu. Derkacheva, Russ. J. Bioorg. Chem., 2013, 39, 677.
O. Yu. Derkacheva, J. Appl. Spectr., Engl. Transl., 2013, 80, 688.
N. N. Chipanina, Yu. R. Mirskova, S. A. Medvedeva, I. V. Volchatova, V. A. Babkin, Chem. Nat. Compd., Engl. Transl., 1995, 31, 392.
O. Faix, Holzforschung, 1986, 40, 273.
R. P. Lastovskii, Metody polucheniya Khimicheskikh reaktivov i preparatov [Methods of Preparation of Chemical Reagents and Intermediate Products], IREA, Moscow, 1974, Issue 26, 351 pp. (in Russian).
G. F. Zakis, Sintez model´nykh soedinenii lignina [Synthesis of Model Lignin Compounds], Zinatne, Riga, 1980, 288 pp. (in Russian).
Gaussion 03 program, Gaussian Inc., Wallingford CT (England), 2004.
S. Sebastian, N. Sundaraganesan, S. Manoharan, Spectrochim. Acta Part A: Mol. Biomol. Spectrosc., 2009, 74, 312.
A. P. Scott, L. Radom, J. Phys. Chem., 1996, 100, 16502.
S. Barsberg, Theor. Chem. Acc., 2015, 134, 33.
O. Derkacheva, D. Sukhov, Macromol. Symp., 2008, 265, 61.
L. L. Landucci, S. A. Ralph, K. E. Hammel, Holzforschung, 1998, 52, 160.
M. Bunzel, Phytochemistry Rev., 2010, 9, 47.
B. H. Monien, B. L. Henry, A. Raghuraman, M. H. U. R. Desai, Bioorg. Med. Chem., 2006, 14, 7988.
M. Bunzel, J. Ralph, J. Agric. Food Chem., 2006, 54, 6409.
L. J. Bellamy, Infrared Spectra of Complex Molecules, Chapman and Hall, London, 1980, 299 pp.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0643—0647, April, 2017.
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Karmanov, A.P., Ishankhodzhaeva, M.M. & Derkacheva, O.Y. Experimental and quantum chemical study of biosynthetic lignin models — dehydropolymers. Russ Chem Bull 66, 643–647 (2017). https://doi.org/10.1007/s11172-017-1785-9
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DOI: https://doi.org/10.1007/s11172-017-1785-9