Application of Fourier transform infrared (FTIR) spectroscopy in the characterization of tannins

Applied Spectroscopy Reviews

Volumn 50, Issue 5, 2015, Pages 407-442

  Ricci, Arianna ^a   Olejar, Kenneth J ^b   Parpinello, Giuseppina P ^a   Kilmartin, Paul A ^b   Versari, Andrea ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

FTIR; peak assignments; tannins

Indexed keywords

FLAVONOIDS; TANNINS;

COMMERCIAL SOURCES; FTIR; MOLECULAR FINGERPRINT; PEAK ASSIGNMENTS; PEAK FREQUENCIES; RELIABLE METHODS; SPECTROSCOPY APPLICATIONS; TECHNOLOGICAL APPLICATIONS;

FOURIER TRANSFORM INFRARED SPECTROSCOPY;

EID: 84929081277     PISSN: 05704928     EISSN: 1520569X     Source Type: Journal    
DOI: 10.1080/05704928.2014.1000461     Document Type: Review

References (154)

1. Ayato, Y., Kunimatsu, K., Osawa, M., and Okada, T. (2006) Study of Pt electrode/nafion ionomer interface in HClO4 by in situ surface-enhanced FTIR spectroscopy. J. Electrochem. Soc., 153: A203-A209.
2. Dovbeshko, G.I., Chegel, V.I., Gridina, N.Y., Repnytska, O.P., Shirshov, Y.M., Tryndiak, V. P., Todor, I.M., and Solyanik, G.I. (2002) Surface enhanced IR absorption of nucleic acids from tumor cells: FTIR reflectance study. Biopolymers, 67: 470-486.
3. Kassi, S., Didriche, K., Lauzin, C., de Ghellinck d'Elseghem Vaernewijckb, X., Rizopoulos, A., and Herman, M. (2010) Demonstration of cavity enhanced FTIR spectroscopy using a femtosecond laser absorption source. Spectrochim. Acta A, 75: 142-145.
4. Yu, P., Jonker,A., andGruber,M. (2009)Molecular basis of protein structure in proanthocyanidin and anthocyanin-enhanced Lc-transgenic alfalfa in relation to nutritive value using synchrotronradiation FTIRmicrospectroscopy: A novel approach. Spectrochim. Acta A, 73: 846-853.
5. Pavlyuchko, A.I., Vasilyev, E.V., and Gribov, L.A. (2011) Calculations of molecular IR spectra in the overtone and combination frequency regions. J. Appl. Spectros., 78: 639-645.
6. Ibrahim, M.N.M., Nadiah, M.Y.N., and Amirue, A.A. (2005) Extraction of tannin from oil palm empty fruit bunch as a rust deactivator. Proceedings of the Regional Symposium on Chemical Engineering 2005, Hanoi, Vietnam, September 29-December 2.
7. Peña, C., de la Caba, K., Retegi, A., Ocando, C., Labidi, J., Echeverria, J.M., and Mondragon, I. (2009) Mimosa and chestnut tannin extracts reacted with hexamine in solution. Journal of Thermal Analysis & Calorimetry, 96: 515-521.
8. Ping, L., Pizzi, A., Guo, Z.D., and Brosse, N. (2012) Condensed tannins from grape pomace: characterization by FTIR and MALDI TOF and production of environment friendly wood adhesive. Ind. Crop Prod., 40: 13-20.
9. Willey, R.R. (1976) Fourier transform infrared spectrophotometer for transmittance and diffuse reflectance measurements. Appl. Spectros., 30: 593-601.
10. Ajuong, E.M.A. and Breese, M.C. (1998) Fourier transform infrared characterization of Pai wood (Afzelia africana Smith) extractives. Holz als Roh-und Werkstoff, 56: 139-142.
11. Jahanshaei, S., Tabarsa, T., and Asghari, J. (2012) Eco-friendly tannin-phenol formaldehyde resin for producing wood composites. Pigment & Resin Technology, 41: 296-301.
12. Rando, R.J., Gibson, R.A., Kwon, C.-W., Poovey, H.G., and Glindmeyer, H.W. (2005) On-filter determination of collected wood dust by diffuse reflectance infrared Fourier-transform spectroscopy (DRIFTS). J. Environ. Monit., 7: 675-680.
13. Stewart, D. (1996) Fourier transform infrared microspectroscopy of plant tissues. Appl. Spectros., 50: 357-365.
14. Vázquez, G., Freire, S., González, J., and Antorrena, G. (2000) Characterization of Pinus pinaster bark and its alkaline extracts by diffuse reflectance Fourier transform infrared (DRIFT) spectroscopy. Holz als Roh-und Werkstoff, 5: 57-61.
15. Harrick, N.J. (1960) Surface chemistry from spectral analysis of totally internally reflected radiation. J. Phys. Chem., 64: 1110-1114.
16. Fahrenfort, J. (1961) Attenuated total reflection: A new principle for the production of useful infra-red reflection spectra of organic compounds. Spectrochim. Acta, 17: 698-709.
17. Alcudia-León, M.C., Lucena, R., Cárdenas, S., and Valcárcel, M. (2008) Dispersive solid phase extraction for in-sorbent surface attenuated total reflection infrared detection. Anal. Chem., 81: 1184-1190.
18. Ortiz, C.M., Castro, I.P., Portilla, L.B., Aranda, P.D., and Arizmendi, M.D.C. (2003) Carbohydrate analysis of floral nectar using medium infrared. Phytochem. Anal., 14: 319-324.
19. Lopez-Sanchez, M., Ayora-Cañada, M.J., and Molina-Diaz, A. (2009) Olive fruit growth and ripening as seen by vibrational spectroscopy. J. Agr. Food Chem., 58: 82-87.
20. Maree, J.E. and Viljoen, A.M. (2012) Phytochemical distinction between Pelargonium sidoides and Pelargonium reniforme - A quality control perspective. S. Afr. J. Bot., 82: 83-91.
21. Mascarenhas, M., Dighton, J., and Arbuckle, G.A. (2000) Characterization of plant carbohydrates and changes in leaf carbohydrate chemistry due to chemical and enzymatic degradation measured by microscopic ATR FT-IR spectroscopy. Appl. Spectros., 54: 681-686.
22. Schulz, H. and Baranska, M. (2007) Identification and quantification of valuable plant substances by IR and Raman spectroscopy. Vib. Spectros., 43: 13-25.
23. Cocciardi, R.A., Ismail, A.A., and Sedman, J. (2005) Investigation of the potential utility of single-bounce attenuated total reflectance Fourier transform infrared spectroscopy in the analysis of distilled liquors and wines. J. Agr. Food Chem., 53: 2803-2809.
24. Cowen, S. and Al-Abadleh, H.A. (2009) DRIFTS studies on the photodegradation of tannic acid as amodel for HULIS in atmospheric aerosols. Phys. Chem. Chem. Phys., 11: 7838-7847.
25. Falcão, L. and Araújo, M.E.M. (2013) Tannins characterization in historic leathers by complementary analytical techniques ATR-FTIR,UV-Vis and chemical tests. J. Cult. Herit., 14: 499-508.
26. Fernández, K. and Agosin, E. (2007) Quantitative analysis of red wine tannins using Fouriertransform mid-infrared spectrometry. J. Agr. Food Chem., 55: 7294-7300.
27. Kozlovskaya, V., Kharlampieva, E., Drachuk, I., Cheng, D., and Tsukruk, V.V. (2010) Responsive microcapsule reactors based on hydrogen-bonded tannic acid layer-by-layer assemblies. Soft Matter, 6: 3596-3608.
28. Laghi, L., Parpinello, G.P., del Rio, D., Calani, L., Mattioli, A.U., and Versari, A. (2010) Fingerprint of enological tannins by multiple techniques approach. Food Chem., 121, 783-788.
29. Nashy, E.H.A., Osman, O., Mahmoud, A.A., and Ibrahim, M. (2012) Molecular spectroscopic study for suggested mechanism of chrome tanned leather. Spectrochim. Acta A, 88: 171-176.
30. Saha, N., Zatloukal, M., and Saha, P. (2003) Modification of polymers by protein hydrolysate - A way to biodegradable materials. Polymer Adv. Technol., 14, 854-860.
31. Yuranova, T., Mosteo, R., Bandara, J., Laub, D., and Kiwi, J. (2006) Self-cleaning cotton textiles surfaces modified by photoactive SiO2/TiO2 coating. J. Mol. Catal. Chem., 244: 160-167.
32. Billes, F. and Mohammed-Ziegler, I. (2007) Vibrational spectroscopy of phenols and phenolic polymers. Theory, experiment, and applications. Appl. Spectros. Rev., 42: 369-441.
33. Cramer, C.J. (2004) Essentials of Computational Chemistry: Theory and Models. 2nd ed. John Wiley & Sons: Hoboken, NJ.
34. Bonacini, I., Prati, S., Quaranta,M., Sciutto, G., Ricci, A., Litti, L.,Meneghetti,M., andMazzeo, R. (2014) Use of nano gold obtained by laser ablation for SEIRA analyses of colorants. Proceedings of the VIII National Congress of Archeometry AIAr, Bologna, Italy, February 5-7.
35. Itoh, J., Sasaki, T., Seo, M., and Ishikawa, T. (1997) In situ simultaneous measurement with IR-RAS and QCM for investigation of corrosion of copper in a gaseous environment. Corros. Sci., 39: 193-197.
36. Khoshhesab, Z.M. (2012) Reflectance IR spectroscopy. In Infrared Spectroscopy - Materials Science, Engineering and Technology. Theophanides, T., Ed. InTech: Rijeka, Croatia, pp. 233-244.
37. Kubelka, P. and Munk, F. (1931) Ein beitrag zur optik der farbanstriche [A contribution to the optics of paints]. Zeitschrift für Technologie und Physik, 12: 593-601.
38. Johannes, D. (1972) Ultrarotspektroskopische Untersuchungen an Polymeren [Infrared Spectroscopy Analysis of Polymers]. Akademie-Verlag: Berlin.
39. Goos, F. and Hanchen, H. (1947) Ein neuer und fundamentaler versuch zur totalreflexion [A new and fundamental test for the total reflection]. Ann. Physik, 1: 333-346.
40. Valeika, V., Sirvaityte, J., and Beelska, K. (2010) Estimation of chrome-free tanning method suitability in conformity with physical and chemical properties of leather. Mater. Sci., 16: 330-336.
41. Versari, A., Laurie, V.F., Ricci, A., Laghi, L., and Parpinello, G.P. (2014) Progress in authentication, typification and traceability of grapes and wines by chemometric approaches. Food Res. Int., 60: 2-18.
42. Wu, Y., Lin, Q., Chen, Z., and Xiao, H. (2011) The interaction between tea polyphenols and rice starch during gelatinization. Food Sci. Technol. Int., 17: 1-9.
43. Brossaud, F., Cheynier, V., and Noble, A.C. (2001) Bitterness and astringency of grape and wine polyphenols. Aust. J. Grape Wine Res., 7: 33-39.
44. Edelmann, A. and Lendl, B. (2002) Toward the optical tongue: Flow-through sensing of tannin-protein interactions based on FTIR spectroscopy. J. Am. Chem. Soc., 124: 14741-14747.
45. Thorngate, J.H. and Noble, A.C. (1995) Sensory evaluation of bitterness and astringency of 3R (+)-epicatechin and 3S(C)-catechin. J. Sci. Food Agr., 67: 531-535.
46. Foo, L.Y. (1981) Proanthocyanidins: Gross chemical structures by infrared spectra. Phytochemistry, 20: 1397-1402.
47. Okuda, T. (2005) Systematics and health effects of chemically distinct tannins in medicinal plants. Phytochemistry, 66: 2012-2031.
48. Versari, A., du Toit, W., and Parpinello, G.P. (2013) Oenological tannins: A review. Aust. J. Grape Wine Res., 19: 1-10.
49. Nyquist, R.A. (2001) Alcohols and phenols. In Interpreting Infrared, Raman, and Nuclear Magnetic Resonance Spectra, 1st ed. Nyquist, R.A., Ed. Academic Press: San Diego, pp. 125-141.
50. Arakawa, H. and Watanabe, N. (1996) Chromium-binding ability of tannin in water-extracts from withered oak leaves. Bull. Chem. Soc. Jpn., 69: 1133-1137.
51. Kamal, S.S.K., Sahoo, P.K., Vimala, J., Premkumar, M., Ram, S., and Durai, L. (2010) A novel green chemical route for synthesis of silver nanoparticles using Camellia sinensis. Acta Chim. Slov., 57: 808-812.
52. Murugananthan,M., Bhaskar Raju, G., and Prabhakar, S. (2005) Removal of tannins and polyhydroxy phenols by electro-chemical techniques. J. Chem. Technol. Biotechnol., 80: 1188-1197.
53. Packialakshmi, N., Suganya, C., and Guru, V. (2014) Phytochemical and IR-spectrum analysis of Strychnos potatorum Linn. Int. J. Phytochem. Pharm., 4: 63-66.
54. Pardeshi, S., Dhodapkar, R., and Kumar, A. (2013) Quantum chemical density functional theory studies on the molecular structure and vibrational spectra of Gallic acid imprinted polymers. Spectrochim. Acta A, 116: 562-573.
55. Bulut, E. and Özacar, M. (2009) Rapid, facile synthesis of silver nanostructure using hydrolyzable tannin. Ind. Eng. Chem. Res., 48: 5686-5690.
56. Kassim, M.J., Hussin, M.H., Achmad, A., Dahon, M.H., Suan, T.K., and Hamdan, H.S. (2011) Determination of total phenols, condensed tannins and flavonoid contents and antioxidant activity of Uncaria gambir extract. J. Pharm., 22: 50-59.
57. Kim, S. and Kim, H.-J. (2003) Curing behavior and viscoelastic properties of pine and wattle tannin-based adhesives studied by dynamic mechanical thermal analysis and FT-IR-ATR spectroscopy. J. Adhes. Sci. Technol., 17: 1369-1383.
58. Costa, E., Coelho, M., Ilharco, L. M., Aguiar-Ricardo, A., and Hammond, P.T. (2011) Tannic acid mediated suppression of PNIPAAm microgels thermoresponsive behavior. Macromolecules, 44: 612-621.
59. Olejar, K.J., Ray, S., Ricci, A., and Kilmartin, P.A. (2014) Superior antioxidant polymer films created through the incorporation of grape tannins in ethyl cellulose. Cellulose, 21 (6): 4545-4556.
60. Nakamoto, K. (2009) Applications in coordination chemistry. In Infrared and Raman Spectra of Inorganic and Coordination Compounds. 6th ed. Nakamoto, K., Ed. John Wiley & Sons: Hoboken, NJ, pp. 1-273.
61. Silverstein, R.M. (1998) Infrared spectrometry. In Spectrometric Identification of Organic Compounds. 6th ed. Silverstein, R.M. and Webster, F.X., Eds. John Wiley & Sons: Chichester, UK, pp. 71-143.
62. Socrates, G. (2000) Infrared and Raman Characteristic Group Frequencies: Tables and Charts. 3rd ed. John Wiley & Sons: Chichester, UK.
63. Tsyganenko, A.A. and Filimonov, V.N. (1973) Infrared spectra of surface hydroxyl groups and crystalline structure of oxides. J. Mol. Struct., 19: 579-589.
64. Khedkar, J.K., Gobre, V.V., Pinjari, R.V., and Gejji, S.P. (2010) Electronic structure and normal vibrations in (C)-catechin and (+)-epicatechin encapsulated-cyclodextrin. J. Phys. Chem. A, 114: 7725-7732.
65. Hu, F., Zhang, Y., Zhang, H., Li, L., and Tian, A. (2010) Density functional theory study on hydrogen bonding interaction of catechin-(H2O)n. Chin. J. Chem., 28: 741-747.
66. Mohammed-Ziegler, I. and Billes, F. (2002) Vibrational spectroscopic calculations on pyrogallol and gallic acid. J. Mol. Struct., 618: 259-265.
67. Birch, A.J., Clark-Lewis, J.W., and Robertson, A.V. (1957). 711. The relative and absolute configurations of catechin and epicatechin. J. Chem. Soc., 1957: 3586-3594.
68. Colthup, N.B. (1964) Infrared spectrometry. In Introduction to Infrared and Raman Spectroscopy. Colthup, N.B., Daly, L.H., and Wiberley, S.E., Eds. Academic Press: New York, pp. 171-213.
69. Mendoza-Wilson, A.M. and Glossman-Mitnik, D. (2006) Theoretical study of the molecular properties and chemical reactivity of (C)-catechin and (+)-epicatechin related to their antioxidant ability. J. Mol. Struct., 761: 97-106.
70. Robb, C.S., Geldart, S.E., Seelenbinder, J.A., and Brown, P.R. (2002) Analysis of green tea constituents by HPLC-FTIR. J. Liq. Chrom. Relat. Technol., 25: 787-801.
71. Senvaitiene, J., Beganskiene, A., and Kareiva, A. (2005) Spectroscopic evaluation and characterization of different historical writing inks. Vib. Spectros., 37: 61-67.
72. Luo, C., Grigsby, W., Edmonds, N., Easteal, A., and Al-Hakkak, J. (2010) Synthesis, characterization, and thermal behaviors of tannin stearates prepared from quebracho and pine bark extracts. J. Appl. Polymer Sci., 117: 352-360.
73. Saayman, H.M. and Roux, D.G. (1965) The origins of tannins and flavonoids in black-wattle barks and heartwoods, and their associated "non-tannin" components. Biochem. J., 97: 794-801.
74. Lei, H., Pizzi, A., and Du, G. (2008) Environmentally friendly mixed tannin/lignin wood resins. J. Appl. Polymer Sci., 107: 203-209.
75. Kumar,G., Karthik, L., andRao, K.V.B. (2010) Antimicrobial activity of latex of Calotropis Gigantea against pathogenic microorganisms - An in vitro study. Pharmacologyonline, 3: 155-163.
76. Kumar, P., Selvi, S.S., Prabha, A.L., Kumar, K.P., Ganeshkumar, R.S., and Govindaraju, M. (2012) Synthesis of silver nanoparticles from Sargassum tenerrimum and screening phytochemicals for its antibacterial activity. Nano Biomed. Eng., 4: 12-16.
77. Ait Baddi, G., Antonio Alburquerque, J., Gonzálvez, J., Cegarra, J., and Hafidi, M. (2004) Chemical and spectroscopic analyses of organic matter transformations during composting of olive mill wastes. International Biodeterioration & Biodegradation, 54: 39-44.
78. Easton, C.D., Jacob, M.V., Shanks, R.A., and Bowden, B.F. (2009) Surface and chemical characterization of polyLA thin films fabricated using plasma polymerization. Chemical Vapor Deposition, 15: 179-185.
79. El Semary, N.A. (2012) The characterization of bioactive compounds from an Egyptian Leptolyngbya sp. strain. Ann. Microbiol., 62: 55-59.
80. Sirvaityte, J., Siugzdaite, J., and Valeika, V. (2011) Application of commercial essential oils of eucalyptus and lavender as natural preservative for leather tanning industry. Rev. Chim. Bucharest, 62: 884-893.
81. Jensen, J.S., Egebo, M., and Meyer, A.S. (2008) Identification of spectral regions for the quantification of red wine tannins with Fourier transform mid-infrared spectroscopy. J. Agr. Food Chem., 56: 3493-3499.
82. Kannan, R.R.R., Arumugam, R., and Anantharaman, P. (2011) Fourier transform infrared spectroscopy analysis of seagrass polyphenols. Current Bioactive Compounds, 7: 118-125.
83. Ogata, T. and Nakano, Y. (2005) Mechanisms of gold recovery from aqueous solutions using a novel tannin gel adsorbent synthesized from natural condensed tannin. Water Res., 39: 4281-4286.
84. Ping, L., Gambier, F., Pizzi, A., Guo, Z.D., and Brosse, N. (2012) Wood adhesives from agricultural by-products: Lignin and tannins for the elaboration of particleboards. Cellulose Chemistry and Technology, 46: 457-462.
85. Zhu, B., Li, J., He, Y., Yamane, H., Kimura, Y., Nishida, H., and Inoue, Y. (2004) Effect of steric hindrance on hydrogen-bonding interaction between polyesters and natural polyphenol catechin. J. Appl. Polymer Sci., 91: 3565-3573.
86. Torreggiani, A., Jurasekova, Z., Sanchez-Cortes, S., and Tamba, M. (2008) Spectroscopic and pulse radiolysis studies of the antioxidant properties of (C)catechin: Metal chelation and oxidizing radical scavenging. J. Raman Spectros., 39: 265-275.
87. Pantoja-Castroa, M.A. and González-Rodriguez, H. (2011) Study by infrared spectroscopy and thermogravimetric analysis of tannins and tannic acid. Rev. Latinoam. Qum., 39: 107-112.
88. Gonultas, O. and Ucar, M.B. (2012) Chemical composition of some commercial tannins produced in Turkey. Proceedings of the 55th International Convention of Society of Wood Science and Technology, Beijing, China, August 27-31.
89. Özacar, M., Şengil, I.A., and Türkmenler, H. (2008) Equilibrium and kinetic data, and adsorption mechanism for adsorption of lead onto valonia tannin resin. Chem. Eng. J., 143: 32-42.
90. Puicá, N.M., Pui, A., and Florescu, M. (2006) FTIR spectroscopy for the analysis of vegetable tanned ancient leather. Eur. J. Sci. Theol., 12: 49-53.
91. Ozgunay, H., Sari, O., and Tozan, M. (2007) Molecular investigation of Valonea tannin. Journal of the American Leather Chemists Association, 102: 154-157.
92. Albu, M.G., Ghica, M.V., Giurginca, M., Trandafir, V., Popa, L., and Cotrut, C. (2009) Spectral characteristics and antioxidant properties of tannic acid immobilized on collagen drugdelivery systems. Rev. Chim. Bucharest, 60: 666-672.
93. Chen, Y.M., Tsao, T.M., Liu, C.C., Huang, P.M., and Wang, M.K. (2010) Polymerization of catechin catalyzed by Mn-, Fe-and Al-oxides. Colloids and Surfaces B: Biointerfaces, 81: 217-223.
94. Araña, J., Tello Rendón, E., Doña Rodriguez, J.M., Herrera Melián, J.A., González Diaz, O., and Pérez Peña, J. (2001) Highly concentrated phenolic wastewater treatment by the photo-Fenton reaction, mechanism study by FTIR-ATR. Chemosphere, 44: 1017-1023.
95. Huang, X., Wu, H., Liao, X., and Shi, B. (2010) One-step, size-controlled synthesis of gold nanoparticles at room temperature using plant tannin. Green Chem., 12: 395-399.
96. Kim, Y.-H., Ogawara, Y., Ogata, T., and Nakano, Y. (2007) Adsorption mechanism of selenite (Se4 C) by redox within condensed-tannin gel under concentrated hydrochloric acid solution. Chem. Lett., 36: 1316-1317.
97. Lin, J.L., Li, C., and Tzeng, W.B. (2004) Mass-analyzed threshold ionization spectroscopy of p-methylphenol and p-ethylphenol cations and the alkyl substitution effect. J. Chem. Phys., 120 (22): 10513-10519.
98. Komal Kumar, J. and Devi Prasad, A.G. (2011) Identification and comparison of biomolecules in medicinal plants of Tephrosia tinctoria and Atylosia albicans by using FTIR. Rom J Biophys., 21 (1): 63-71.
99. Anderson, R.J., Bendell, D.J., and Groundwater, P.W. (2004) Infrared spectroscopy. In Organic Spectroscopic Analysis. Abel, E. W., Ed. Royal Society of Chemistry: Cambridge, UK, pp. 24-50.
100. Coates, J. (2000) Interpretation of infrared spectra, a practical approach. In Encyclopedia of Analytical Chemistry. Meyers, R.A., Ed. John Wiley & Sons: Chichester, UK, pp. 10815-10837.
101. Varsanyi, G. and Szöke, S. (1969) Normal vibrations of benzene and its derivatives. In Vibrational Spectra of Benzene Derivatives. Varsányi, G., Ed. Academic Press: New York, pp. 141-393.
102. Ehrhardt, S.M. (1984) An investigation of the vibrational spectra of lignin model compounds. Doctoral Dissertation, The Institute of Paper Chemistry, Appleton, Wisconsin.
103. Beg, M.A.A. and Siddiq, Z.A. (1969) Infrared spectroscopic investigation of tannins. Die Angew. Makromol. Ghem., 7 (63): 67-78.
104. Garcia, A., Toledano, A., Andrés, M.A., and Labidi, J. (2010) Study of the antioxidant capacity of Miscanthus sinensis lignins. Proc. Biochem., 45: 935-940.
105. Michalska, D., Bienko, D.C., Abkowicz-Bienko, A.J., and Latajka, Z. (1996) Density functional, Hartree-Fock, and MP2 studies on the vibrational spectrum of phenol. J. Phys. Chem., 100: 17786-17790.
106. Bist, H.D., Brand, J.C.D., and Williams, D.R. (1966) The 2750-A electronic band system of phenol. Part I. The in-plane vibrational spectrum. J. Mol. Spectros., 21: 76-98.
107. Stymnea, B., Sauvage, F.X., and Wettermark, G.A. (1979) Spectroscopic study of the complexation of phthalocyanines with water, ethanol and phenol. Spectrochim. Acta A, 35 (10): 1195-1201.
108. Lampert, H., Mikenda, W., and Karpfen, A. (1997) Molecular geometries and vibrational spectra of phenol, benzaldehyde, and salicylaldehyde: Experimental versus quantum chemical data. J. Phys. Chem. A, 101: 2254-2263.
109. Madhan, B., Muralidharan, C., and Jayakumar, R. (2002) Study on the stabilisation of collagen with vegetable tannins in the presence of acrylic polymer. Biomaterials, 23: 2841-2847.
110. Grishechko, L.I., Amaral-Laba, G., Szczureka, A., Fierroa, V., Kuznetsov, B.N., Pizzi, A., and Celzarda, A. (2013) New tannin-lignin aerogels. Ind. Crop. Prod., 41: 347-355.
111. Falcão, L. and Araújo, M.E.M. (2014) Application of ATR-FTIR spectroscopy to the analysis of tannins in historic leathers: The case study of the upholstery from the 19th century Portuguese Royal Train. Vib. Spectros., 74: 98-103.
112. Iglesias, J., Garcia de Saldana, E., and Jaén, J.A. (2001) On the tannic acid interaction with metallic iron. Hyperfine Interact., 134: 109-114.
113. Cappelli, C., Mennucci, B., and Monti, S. (2005) Environmental effects on the spectroscopic properties of gallic acid: A combined classical and quantum mechanical study. J. Phys. Chem. A, 109: 1933-1943.
114. Schnabel, T., Musso, M., and Tondi, G. (2014) Univariate and multivariate analysis of tanninimpregnated wood species using vibrational spectroscopy. Appl. Spectros., 68 (4): 488-494.
115. Arana, J., Tello Rendon, E., Dona Rodriguez, J.M., Herrera Melian, J.A., Gonzales Diaz, O., and Perez Pena, J. (2001) Highly concentrated phenolic wastewater treatment by the photo Fenton reaction, mechanism study by FTIR-ATR. Chemosphere, 44: 1017-1023.
116. Maoela, M.S., Arotiba, O.A., Baker, P.G.L., Mabusela, W.T., Jahed, N., Songa, E.A., and Iwuoha, E.I. (2009) Electroanalytical determination of catechin flavonoid in ethyl acetate extracts of medicinal plants. Int. J. Electrochem. Sci., 4: 1497-1510.
117. Rangel-Vázquez, N.A. and Félix, F.R. (2014) Computational Chemistry Applied in the Analyses of Chitosan/Polyvinylpyrrolidone/Mimosa tenuiflora. Science Publishing Group: New York.
118. Vedulla, S., Parameswari, S.A., and Gopinath, C. (2013) Isolation of active compound in Ficus religiosa Linn. Int. J. Pharmaceut. Phytochem. Res., 5 (1): 60-65.
119. Ahmad, L.O., Linh, L.H.M., Akimoto, M., Kaneki, Y., Honda, M., Suda, M., and Kunimoto, K.K. (2013) Persimmon tannin gel: Formation by autoxidation and caffeine adsorption properties. Food Sci. Technol. Res., 19 (4): 697-703.
120. Pervan, S., Prekrat, S., Gorisek, Z, Straze, A. and Humar,M. (2006) Effect of steaming on colour and chemistry of cherrywood (Prunus avium L.). Wood Structure and Properties, 6: 331-336.
121. Patil Daulat, G. and Nikam Shashikant, V. (2014) In-vitro antioxidant activity and biochemical analysis of Persicara glabra. Int. J. Adv. Pharmaceut. Res., 5 (2): 121-129.
122. Ankamwar, B. (2010) Biosynthesis of gold nanoparticles (green-gold) using leaf extract of Terminalia catappa. E-Journal of Chemistry, 7 (4): 1334-1339.
123. Iswantini, D., Ramdhani, T.H., and Darusman, L.K. (2012) In vitro inhibition of celery (Apium graveolens L.) extract on the activity of xanthine oxidase and determination of its active compound. Indo. J. Chem., 12 (3): 247-254.
124. Eddy, N.O. (2009) Inhibitive and adsorption properties of ethanol extract of Colocasia esculenta leaves for the corrosion of mild steel in H2SO4. Int. J. Phys. Sci., 4 (4): 165-171.
125. Agatonovic-Kustrin, S., Morton, D.W., and Yusof, A.P.M. (2013) The use of Fourier transform infrared (FTIR) spectroscopy and artificial neural networks (ANNs) to assess wine quality. Mod. Chem. Appl., 1 (4): 1-8.
126. Lee, Y.H. (2007) Dyeing, fastness, and deodorizing properties of cotton, silk, and wool fabrics dyed with coffee sludge (Coffea arabica L.) extract. J. Appl. Polymer Sci., 103 (1): 251-257.
127. Ahmada, A., Rafatullah, M., Sulaiman, O., Ibrahima, M.H., and Hashim, R. (2009) Scavenging behaviour of meranti sawdust in the removal of methylene blue from aqueous solution. J. Hazard. Mater., 170 (1): 357-365.
128. Verma, S.M. and Suresh, K.B. (2002) Phytochemical investigations of Indigofera tinctoria Linn leaves. Ancient Sci. Life, 21 (4): 235-239.
129. Dimitric-Markovic, J.M., Mioc, U.B., Baranac, J.M., and Nedic, Z.P. (2001) A study of the IR spectra of the copigments of malvin chloride with organic acids. J. Serb. Chem. Soc., 66 (7): 451-462.
130. Ashokkumar, R. and Ramaswamy, M. (2014) Phytochemical screening by FTIR spectroscopic analysis of leaf extracts of selected Indian medicinal plants. Int. J. Curr. Microbiol. Appl. Sci., 3 (1): 395-406.
131. Sawiñska, D., Polewski, K., Rolewski, P., and Sawiñski, J. (2007) Synthesis and properties of model humic substances derived from gallic acid. Int. Agrophys., 21: 199-208.
132. Sidirasa, D., Batziasa, F., Schroederb, E., Ranjanc, R., and Tsapatsisc, M. (2011) Dye adsorption on autohydrolyzed pine sawdust in batch and fixed-bed systems. Chem. Eng. J., 171 (3): 883-896.
133. Skudra, S., Shulga, G., and Reihmane, S. (2011) The study of birch lignin isolated from hydrolyzate imitating wastewater of veneer production. Scientific Journal of Riga Technical University, Material Science and Applied Chemistry, 22: 122-126.
134. Sheny, D.S., Philip, D., and Mathew, J. (2013) Synthesis of platinum nanoparticles using dried Anacardium occidentale leaf and its catalytic and thermal applications. Spectrochim. Acta A, 114: 267-271.
135. Anil Singh, S., Bora, T.C., and Rajmuhon Singh, N. (2012) Preliminary phytochemical analysis and antimicrobial potential of fermented Bambusa balcooa shoots. The Bioscan, 7 (3): 391-394.
136. Perez, M.G., Martin-Netoa, L., Saabb, S.C., Novotnya, E.H., Miloria, D.M.B.P., Bagnatod, V. S., Colnagoa, L.A., Meloe, W.J., and Knicker, H. (2004) Characterization of humic acids from a Brazilian oxisol under different tillage systems by EPR, 13C NMR, FTIR and fluorescence spectroscopy. Geoderma, 118: 181-190.
137. Suarez-Hernandez, R., Dominguez-Patiño, G., Tello, I., and Gonzalez-Rodriguez, J.G. (2014) Ganoderma lucidum extract as corrosion inhibitor for carbon steel in H2SO4. Chem. Sci. Rev. Lett., 3 (11): 425-435.
138. Bodrláu, R., Teacá, C.A., Roşu, D., Roşu, L., Varganici, C.D., and Coroabá, A. (2013) Physico-chemical properties investigation of softwood surface after treatment with organic anhydride. Cent. Eur. J. Chem., 11 (12): 2098-2106.
139. Flakus, H.T. and Chelmecki, M. (2002) Infrared spectra of the hydrogen bond in benzoic acid crystals: Temperature and polarization effects. Spectrochim. Acta A, 58: 179-196.
140. Odozi, T.O. and Agiri, G.O. (1986) Wood adhesives from modified red onion skin tannin extract. Agr. Waste., 17: 59-65.
141. Ugovs̈ek, A., Budija, F., Kariź, M., and ͆ernek, M. (2011) The influence of solvent content in liquefied wood and of the addition of condensed tannin on bonding quality. Drvna Industrija, 62 (2): 87-95.
142. da Costa, A.C.A., da Fonseca, N.F., de Carvalho, S.S., dos Santos, F.C.S.C., Barki, L., de Freitas, D.S., Herbst, M.H., and Lutterbach, M.T.S. (2013) Archaeometric investigations on naturally and thermally-aged iron-gall inks using different tannin sources. Cent. Eur. J. Chem., 11 (11): 1729-1739.
143. FreireHadija, O. and Spoljar, B. (1995) Quantitative determination of carboxylate by infrared spectroscopy: Application to humic acids. Fresen. J. Anal. Chem., 351: 692-693.
144. Argun, M.E. and Dursun, Ş. (2008) Cadmium removal using activated pine bark. J. Int. Environ. Appl. Sci., 3 (1): 37-42.
145. Carlborn, K. and Matuana, L.M. (2005) Composite materials manufactured from wood particles modified through a reactive extrusion process. Polymer Compos., 26 (4): 534-541.
146. Taddei, P., Monti, P., Freddi, G., Araic, T., and Tsukad, M. (2003) Binding of Co(II) and Cu (II) cations to chemically modified wool fibres: An IR investigation. J. Mol. Struct., 650: 105-113.
147. Lei, H., Pizzi, A., and Du, G. (2008) Environmentally friendly mixed tannin/lignin wood resins. J. Appl. Polymer Sci., 107 (1): 203-209.
148. Ooa, C.W., Kassima, M.J., and Pizzi, A. (2009) Characterization and performance of Rhizophora apiculata mangrove polyflavonoid tannins in the adsorption of copper (II) and lead (II). Ind. Crop. Prod., 30: 152-161.
149. Jastrzebska, M., Zalewska-Rejdak, J., Wrzalik, R., Kocot, A., Mroz, I., Barwinski, B., Turek, A., and Cwalina, B. (2006) Tannic acid-stabilized pericardium tissue: IR spectroscopy, atomic force microscopy, and dielectric spectroscopy investigations. J. Biomed. Mater. Res. A, 78A (1): 148-156.
150. He, L., Gao, S.Y., Wu, H., Liao, X.P., He, Q., and Shi, B. (2012) Antibacterial activity of silver nanoparticles stabilized on tannin-grafted collagen fiber. Mater. Sci. Eng. C, 32: 1050-1056.
151. Xiang, H., Li, L., Wang, S., Wang, R., Cheng, Y., Zhou, Z., and Zhu, M. (in press) Natural polyphenol tannic acid reinforced poly(3-hydroxybutyrate-co-3-hydroxyvalerate) composite films with enhanced tensile strength and fracture toughness. Polymer Compos.
152. Billes, F., Mohammed-Ziegler, I., and Bombicz, P. (2007) Vibrational spectroscopic study on the quantum chemical model and the X-ray structure of gallic acid, solvent effect on the structure and spectra. Vib. Spectros., 43: 193-202.
153. Bozić, M., Gorgieva, S., and Kokol, V. (2012) Homogeneous and heterogeneous methods for laccase-mediated functionalization of chitosan by tannic acid and quercetin. Carbohydr. Polymer., 89: 854-864.
154. Limaye, M.V., Bacsik, Z., Schütz, C., Dembelé, A., Pléa, M., Andersson, L., Salazar-Alvarez, G., and Bergstrm, L. (2012) On the role of tannins and iron in the Bogolan or mud cloth dyeing process. Textil. Res. J., 82: 1888-1896.