Investigation of electronic and optical properties of nano-Ag produced from heterocyclic compounds by green chemistry reactions
Year 2023,
Volume: 10 Issue: 4, 605 - 625, 01.12.2023
Aslı Öztürk Kiraz
,
Mine Sulak
,
Yeşim Kara
,
İzzet Kara
Abstract
The synthesis of nanoparticles using biological molecules has become one of the current research areas due to the high toxic content, poor stability, and expensive production technologies of nanoparticles synthesized by physical and chemical technologies. With the approach called green synthesis, nanoparticles that do not contain toxic substances have been produced in a method that does not harm the environment and human health. The number of polyphenol compounds in the ethyl alcohol/water extract of propolis collected from the Muğla-Türkiye region was determined. The synthesis and characterization of silver nanoparticles were carried out using the ethyl alcohol/water extract of propolis. The descriptions of the synthesized nanoparticles were made using ultraviolet-visible absorption and attenuated total reflection-Fourier transform infrared. Scanning electron microscopy, energy-dispersive X-ray, and X-ray diffraction methods were used for morphological examinations. Which polyphenol compound in the propolis content is effective in the synthesis of nanosilver particles was investigated with a Gaussian 16 package program. The electronic properties of the compounds were obtained by density functional theory using boundary orbitals theory, molecular electrostatic surface potential, and nonlinear optical properties. Epigallocatechin gallate, Kaempferol, and Quercetin are effective in obtaining nano-Ag and can be used as organic optical material in technology.
Project Number
2018FEBE002, 2020FEBE012
References
- Abegg, P.W., Ha, T.K. (1974). Ab initio calculation of spin-orbit-coupling constant from Gaussian lobe SCF molecular wavefunctions. Molecular Physics, 27, 763-767. https://doi.org/10.1080/00268977400100661
- Al-Fakeh, M.S., Osman, S.O.M., Gassoumi M., Rabhi M., Omer, M. (2021). Characterization, antimicrobial and anticancer properties of palladium nanoparticles biosynthesized optimally using Saudi propolis. Nanomaterials, 11, 2666. https://doi.org/10.3390/nano11102666
- Anklam, E. (1998). A review of the analytical methods to determine the geographical and botanical origin of honey. Food Chemistry, 63, 549–562. https://doi.org/10.1016/S0308-8146(98)00057-0
- Arivazhagan, M., Kavitha, R. (2012). Molecular structure, vibrational spectroscopic, NBO, HOMO-LUMO and Mulliken analysis of 4-methyl-3-nitro benzyl chloride. Journal of Molecular Structure, 1011, 111 120. https://doi.org/10.1016/j.molstruc.2011.12.006
- Benzie, I.F., Strain, J.J. (1999). Ferric reducing/antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods Enzymol., 299, 15–27. https://doi.org/10.1016/s0076-6879(99)99005-5
- Bhattacharya, R., Mukherjee, P. (2008). Biological properties of “naked” metal nanoparticles. Advanced Drug Delivery Reviews, 60(11), 1289 1306. https://doi.org/10.1016/j.addr.2008.03.013
- Das, R, Nath, S.S., Chakdar, D., Gope, G., Bhattacharjee, R. (2009). Preparation of silver nanoparticles and their characterization. Journal of Nanotechnology, 5, 1-6.
- Dege, N., Senyüz, N., Batı, H., Günay, N., Avcı, D., Tamer, Ö., Atalay, Y. (2014). The synthesis, characterization and theoretical study on nicotinic acid [1-(2,3-dihydroxyphenyl) methylidene)hydrazide. Spectrochim Acta A Mol. Biomol. Spectrosc., 120, 323–331. https://doi.org/10.1016/j.saa.2013.10.030
- Dehvari, M., Ghahghaei, A. (2018). The effect of green synthesis silver nanoparticles (AgNPs) from Pulicaria undulata on the amyloid formation in α-lactalbumin and the chaperon action of α-casein. International Journal of Biological Macromolecules, 108, 1128-1139. https://doi.org/10.1016/j.ijbiomac.2017.12.040
- Dennington, R., Keith, T.A., Millam, J.M. (2016). GaussView, Version 6. (Shawnee Mission KS, Semichem Inc.
- Eşme, A., Sağdınç, S.G. (2014). The linear, nonlinear optical properties and quantum chemical parameters of some sudan dyes. J BAUN Inst. Sci. Technol., 16(1), 47-75.
- Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., … & Fox, D.J. (2016). Gaussian 16, Revision C.01, Gaussian, Inc., Wallingford CT.
- Fukui, K. (1982). Role of frontier orbitals in chemical reactions. Science, 218, 747– 754. https://doi.org/10.1126/science.218.4574.747
- Fukumoto L.R., Mazza G. (2000) Assessing antioxidant and prooxidant activities of phenolic compounds. J. Agric. Food Chem., 48, 3597-3604. https://doi.org/10.1021/jf000220w
- Gautam, A, Singh, G.P., Ram, S. (2007). A simple polyol synthesis of silver metal nanopowder of uniform particles. Synth. Met., 157, 5-10. https://doi.org/10.1016/j.synthmet.2006.11.009
- Geethalakshmi, R., Sarada, D.V. (2012). Gold and silver nanoparticles from Trianthema decandra: synthesis, characterization, and antimicrobial properties. Int. J. Nanomedicine, 7, 5375-5384. https://doi.org/10.2147/IJN.S36516
- Govindarajan, M., Karabacak, M., Suvitha, A., Periandy, S. (2012). FT-IR, FT-Raman, ab initio, HF and DFT studies, NBO, HOMO-LUMO and electronic structure calculations on 4-chloro 3 nitrotoluene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 89, 137 148. https://doi.org/10.1016/j.saa.2011.12.067
- Hojat, V., Azizi, S., Mohammadi, P. (2018). Green synthesis of the silver nanoparticles mediated by thymbra spicata extract and its application as a heterogeneous and recyclable nanocatalyst for catalytic reduction of a variety of dyes in water. Journal of Cleaner Production. 170, 1536-1543. https://doi.org/10.1016/j.jclepro.2017.09.265
- Jain, S., Mehata, M.S. (2017). Medicinal plant leaf extract and pure flavonoid mediated green synthesis of silver nanoparticles and their enhanced antibacterial property. Scientific Reports, 7(1), 15867. https://doi.org/10.1038/s41598-017-15724-8
- Jasrotia, T., Chaudhary, S, Kaushik, A., Kumar, R., Chaudhary, G.R. (2020). Green chemistry-assisted synthesis of biocompatible Ag, Cu, and Fe2O3 nanoparticles. Materials Today Chemistry, 15, 100214. https://doi.org/10.1016/j.mtchem.2019.100214
- Karthick, T., Balachandran, V., Perumal, S., Nataraj, A. (2011). Rotational isomers, vibrational assignments, HOMO-LUMO, NLO properties and molecular electrostatic potential surface of N-(2 bromoethyl) phthalimide. Journal of Molecular Structure, 1005, 202–213. https://doi.org/10.1016/j.molstruc.2011.08.051.
- Kleinman, D.A. (1962) Nonlinear Dielectric Polarization in Optical Media. Physical Review, 126, 1977-1979. https://doi.org/10.1103/PhysRev.126.1977
- Krell, R. (1996). Value-Added Products from Beekeeping. Fao Agricultural Services Bulletin No. 124 Chapter 3, Pollen.
- Lakshman Kumar, D., Siva Sankar, S., Venkatesh, P., Hepcy Kalarani, D. (2016). Green synthesis of silver nanoparticles using aerial parts extract of Echinochloa colona and their characterization. European J. Pharm. Med. Res., 3(4), 325-328.
- Mason, S.E., Iceman, C.R., Trainor, T.P., Chaka, A.M. (2010). Molecular-level understanding of environmental interfaces using density functional theory modeling. Physics Procedia, 4, 67–83. https://doi.org/10.1016/j.phpro.2010.08.010
- Murray, J.S., & Sen, K. (1996). Molecular Electrostatic Potentials, Concepts and Applications. Elsevier.
- Oyaizu, M. (1986). Studies on product of browning reaction prepared from glucose amine. Jpn. J. Nutr. Diet., 44, 307-315. https://doi.org/10.5264/eiyogakuzashi.44.307
- Padil, V.V.T., Cernik, M. (2013). Green synthesis of copper oxide nanoparticles using gum karaya as a biotemplate and their antibacterial application. International Journal of Nanomedicine, 8, 889-898. https://doi.org/10.2147/IJN.S40599
- Petri, G., Lemberkovics, E., & Foldvari, M. (1988). Examination of Differences Between Propolis (Bee Glue) Produced from Different Floral Environments. In: Flavours and Fragrances: a world perspective. Lawrence, B.M., Mookherjee, B.D., Willis, B.J. (Eds.) Elsevier Sci. PubI., Amsterdam, pp 439-446.
- Pipek, J., Mezey, P.Z. (1989). A fast intrinsic localization procedure applicable for ab initio and semiempirical linear combination of atomic orbital wave functions. The Journal of Chemical Physics, 90, 4916. https://doi.org/10.1063/1.456588
- Prashanth, J., Ramesh, G., Naik, J., Ojha, J., Reddy, B., Rao, G. (2015). Molecular structure, vibrational analysis and first order hyperpolarizability of 4-Methyl-3-Nitrobenzoic Acid using density functional theory. Optics and Photonics Journal, 5, 91-107. https://doi.org/10.4236/opj.2015.53008
- Prior, R.L., Hoang, H., Gu, L., Wu, X., Bacchocca, M., Howard, L., Hampsch-Woodill, M., Huang, D., Ou, B., Jacob, R. (2003). Assays for hydrophilic and lipophilic antioxidant capacity (oxygen radical absorbance capacity (ORACFL)) of plasma and other biological and food samples. J. Agric. Food. Chem., 51, 3273-3279. https://doi.org/10.1021/jf0262256
- Ramnath, S. (2017). Synthesis of copper nanoparticles from bee propolis extract and its antibacterial property. European J. Pharm. Med. Res., 4, 684-688.
- Santhoshkumar, J., Venkat, Kumar, S., Rajeshkumar, S. (2017). Synthesis of zinc oxide nanoparticles using plant leaf extract against urinary tract infection pathogen. Resource- Efficient Technologies, 3(4), 459-465. https://doi.org/10.1016/j.reffit.2017.05.001
- Scrocco, E., Tomasi, J. (1978). Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials. Advances in Quantum Chemistry, 11, 115–121. https://doi.org/10.1016/S0065-3276(08)60236-1
- Siddiquee, M.A., Ud din Parray, M., Mehdi, S.H., Alzahrani, K.A., Alshehri, A.A., Malik, M.A., Patel, R. (2020). Green synthesis of silver nanoparticles from delonix regia leaf extracts: in-vitro cytotoxicity and interaction studies with bovine serum albumin. Materials Chemistry and Physics, 242, 122493. https://doi.org/10.1016/j.matchemphys.2019.122493
- Singleton, V.L., & Rossi, J.A. (1965) Colorimetry of Total Phenolics with Phosphomolybdic-Phosphotungstic Acid Reagent. American Journal of Enology and Viticulture, 16, 144-158.
- Singleton, V.L., Orthofer, R., Lamuela-Raventos, R.M. (1999). Analysis of total phenols and other oxidation substrates and antioxidants by means of folin-ciocalteu reagent. Methods in Enzymology, 299, 152-178. http://dx.doi.org/10.1016/S0076-6879(99)99017-1
- Slinkard, K., Singleton, V.L. (1977). Total phenol analysis: automation and comparison with manual methods. American Journal of Enology and Viticulture, 28(1), 49-55.
- Stevens, J. (2017). Virtually going green: The role of quantum computational chemistry in reducing pollution and toxicity in chemistry. Physical Sciences Reviews, 2(7), 20170005. https://doi.org/10.1515/psr-2017-0005
- Tejamaya, M., Roemer, I., Merrifield, R.C., Lead, J.R. (2012). Stability of citrate, PVP, and PEG coated silver nanoparticles in ecotoxicology media. Environ. Sci. Technol., 46, 7011-7017. https://doi.org/10.1021/es2038596
- Trindle, C., Crum, P., Douglass, K. (2003). G2(MP2) Characterization of Conformational Preferences in 2-Substituted Ethanols (XCH2CH2OH) and Related Systems. J. Phys. Chem. A, 107, 6236. https://doi.org/10.1021/jp034598j
- Tsipis, A.C. (2014). DFT flavor of coordination chemistry. Coordination Chemistry Reviews, 272, 1–29. https://doi.org/10.1016/j.ccr.2014.02.023
- Van Mourik, T., Bühl, M., Gaigeot, M.P. (2014). Density functional theory across chemistry, physics, and biology. Philosophical Transactions of the Royal Society A., 372, 20120488. https://doi.org/10.1098/rsta.2012.0488
- Velammal, S.P., Devi, T.A., Amaladhas, T.P. (2016). Antioxidant, antimicrobial and cytotoxic activities of silver and gold nanoparticles synthesized using Plumbago zeylanica bark. Journal of Nanostructure in Chemistry, 6, 247-260. https://doi.org/10.1007/s40097-016-0198-x
- Weinhold, F. (1998). Natural Bond Orbital Methods In: Encyclopedia of Computational Chemistry 3, John Wiley and Sons.
Investigation of electronic and optical properties of nano-Ag produced from heterocyclic compounds by green chemistry reactions
Year 2023,
Volume: 10 Issue: 4, 605 - 625, 01.12.2023
Aslı Öztürk Kiraz
,
Mine Sulak
,
Yeşim Kara
,
İzzet Kara
Abstract
The synthesis of nanoparticles using biological molecules has become one of the current research areas due to the high toxic content, poor stability, and expensive production technologies of nanoparticles synthesized by physical and chemical technologies. With the approach called green synthesis, nanoparticles that do not contain toxic substances have been produced in a method that does not harm the environment and human health. The number of polyphenol compounds in the ethyl alcohol/water extract of propolis collected from the Muğla-Türkiye region was determined. The synthesis and characterization of silver nanoparticles were carried out using the ethyl alcohol/water extract of propolis. The descriptions of the synthesized nanoparticles were made using ultraviolet-visible absorption and attenuated total reflection-Fourier transform infrared. Scanning electron microscopy, energy-dispersive X-ray, and X-ray diffraction methods were used for morphological examinations. Which polyphenol compound in the propolis content is effective in the synthesis of nanosilver particles was investigated with a Gaussian 16 package program. The electronic properties of the compounds were obtained by density functional theory using boundary orbitals theory, molecular electrostatic surface potential, and nonlinear optical properties. Epigallocatechin gallate, Kaempferol, and Quercetin are effective in obtaining nano-Ag and can be used as organic optical material in technology.
Supporting Institution
Pamukkale Üniversitesi
Project Number
2018FEBE002, 2020FEBE012
Thanks
TÜBİTAK ULAKBİM (TRUBA Resorces)
References
- Abegg, P.W., Ha, T.K. (1974). Ab initio calculation of spin-orbit-coupling constant from Gaussian lobe SCF molecular wavefunctions. Molecular Physics, 27, 763-767. https://doi.org/10.1080/00268977400100661
- Al-Fakeh, M.S., Osman, S.O.M., Gassoumi M., Rabhi M., Omer, M. (2021). Characterization, antimicrobial and anticancer properties of palladium nanoparticles biosynthesized optimally using Saudi propolis. Nanomaterials, 11, 2666. https://doi.org/10.3390/nano11102666
- Anklam, E. (1998). A review of the analytical methods to determine the geographical and botanical origin of honey. Food Chemistry, 63, 549–562. https://doi.org/10.1016/S0308-8146(98)00057-0
- Arivazhagan, M., Kavitha, R. (2012). Molecular structure, vibrational spectroscopic, NBO, HOMO-LUMO and Mulliken analysis of 4-methyl-3-nitro benzyl chloride. Journal of Molecular Structure, 1011, 111 120. https://doi.org/10.1016/j.molstruc.2011.12.006
- Benzie, I.F., Strain, J.J. (1999). Ferric reducing/antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods Enzymol., 299, 15–27. https://doi.org/10.1016/s0076-6879(99)99005-5
- Bhattacharya, R., Mukherjee, P. (2008). Biological properties of “naked” metal nanoparticles. Advanced Drug Delivery Reviews, 60(11), 1289 1306. https://doi.org/10.1016/j.addr.2008.03.013
- Das, R, Nath, S.S., Chakdar, D., Gope, G., Bhattacharjee, R. (2009). Preparation of silver nanoparticles and their characterization. Journal of Nanotechnology, 5, 1-6.
- Dege, N., Senyüz, N., Batı, H., Günay, N., Avcı, D., Tamer, Ö., Atalay, Y. (2014). The synthesis, characterization and theoretical study on nicotinic acid [1-(2,3-dihydroxyphenyl) methylidene)hydrazide. Spectrochim Acta A Mol. Biomol. Spectrosc., 120, 323–331. https://doi.org/10.1016/j.saa.2013.10.030
- Dehvari, M., Ghahghaei, A. (2018). The effect of green synthesis silver nanoparticles (AgNPs) from Pulicaria undulata on the amyloid formation in α-lactalbumin and the chaperon action of α-casein. International Journal of Biological Macromolecules, 108, 1128-1139. https://doi.org/10.1016/j.ijbiomac.2017.12.040
- Dennington, R., Keith, T.A., Millam, J.M. (2016). GaussView, Version 6. (Shawnee Mission KS, Semichem Inc.
- Eşme, A., Sağdınç, S.G. (2014). The linear, nonlinear optical properties and quantum chemical parameters of some sudan dyes. J BAUN Inst. Sci. Technol., 16(1), 47-75.
- Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., … & Fox, D.J. (2016). Gaussian 16, Revision C.01, Gaussian, Inc., Wallingford CT.
- Fukui, K. (1982). Role of frontier orbitals in chemical reactions. Science, 218, 747– 754. https://doi.org/10.1126/science.218.4574.747
- Fukumoto L.R., Mazza G. (2000) Assessing antioxidant and prooxidant activities of phenolic compounds. J. Agric. Food Chem., 48, 3597-3604. https://doi.org/10.1021/jf000220w
- Gautam, A, Singh, G.P., Ram, S. (2007). A simple polyol synthesis of silver metal nanopowder of uniform particles. Synth. Met., 157, 5-10. https://doi.org/10.1016/j.synthmet.2006.11.009
- Geethalakshmi, R., Sarada, D.V. (2012). Gold and silver nanoparticles from Trianthema decandra: synthesis, characterization, and antimicrobial properties. Int. J. Nanomedicine, 7, 5375-5384. https://doi.org/10.2147/IJN.S36516
- Govindarajan, M., Karabacak, M., Suvitha, A., Periandy, S. (2012). FT-IR, FT-Raman, ab initio, HF and DFT studies, NBO, HOMO-LUMO and electronic structure calculations on 4-chloro 3 nitrotoluene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 89, 137 148. https://doi.org/10.1016/j.saa.2011.12.067
- Hojat, V., Azizi, S., Mohammadi, P. (2018). Green synthesis of the silver nanoparticles mediated by thymbra spicata extract and its application as a heterogeneous and recyclable nanocatalyst for catalytic reduction of a variety of dyes in water. Journal of Cleaner Production. 170, 1536-1543. https://doi.org/10.1016/j.jclepro.2017.09.265
- Jain, S., Mehata, M.S. (2017). Medicinal plant leaf extract and pure flavonoid mediated green synthesis of silver nanoparticles and their enhanced antibacterial property. Scientific Reports, 7(1), 15867. https://doi.org/10.1038/s41598-017-15724-8
- Jasrotia, T., Chaudhary, S, Kaushik, A., Kumar, R., Chaudhary, G.R. (2020). Green chemistry-assisted synthesis of biocompatible Ag, Cu, and Fe2O3 nanoparticles. Materials Today Chemistry, 15, 100214. https://doi.org/10.1016/j.mtchem.2019.100214
- Karthick, T., Balachandran, V., Perumal, S., Nataraj, A. (2011). Rotational isomers, vibrational assignments, HOMO-LUMO, NLO properties and molecular electrostatic potential surface of N-(2 bromoethyl) phthalimide. Journal of Molecular Structure, 1005, 202–213. https://doi.org/10.1016/j.molstruc.2011.08.051.
- Kleinman, D.A. (1962) Nonlinear Dielectric Polarization in Optical Media. Physical Review, 126, 1977-1979. https://doi.org/10.1103/PhysRev.126.1977
- Krell, R. (1996). Value-Added Products from Beekeeping. Fao Agricultural Services Bulletin No. 124 Chapter 3, Pollen.
- Lakshman Kumar, D., Siva Sankar, S., Venkatesh, P., Hepcy Kalarani, D. (2016). Green synthesis of silver nanoparticles using aerial parts extract of Echinochloa colona and their characterization. European J. Pharm. Med. Res., 3(4), 325-328.
- Mason, S.E., Iceman, C.R., Trainor, T.P., Chaka, A.M. (2010). Molecular-level understanding of environmental interfaces using density functional theory modeling. Physics Procedia, 4, 67–83. https://doi.org/10.1016/j.phpro.2010.08.010
- Murray, J.S., & Sen, K. (1996). Molecular Electrostatic Potentials, Concepts and Applications. Elsevier.
- Oyaizu, M. (1986). Studies on product of browning reaction prepared from glucose amine. Jpn. J. Nutr. Diet., 44, 307-315. https://doi.org/10.5264/eiyogakuzashi.44.307
- Padil, V.V.T., Cernik, M. (2013). Green synthesis of copper oxide nanoparticles using gum karaya as a biotemplate and their antibacterial application. International Journal of Nanomedicine, 8, 889-898. https://doi.org/10.2147/IJN.S40599
- Petri, G., Lemberkovics, E., & Foldvari, M. (1988). Examination of Differences Between Propolis (Bee Glue) Produced from Different Floral Environments. In: Flavours and Fragrances: a world perspective. Lawrence, B.M., Mookherjee, B.D., Willis, B.J. (Eds.) Elsevier Sci. PubI., Amsterdam, pp 439-446.
- Pipek, J., Mezey, P.Z. (1989). A fast intrinsic localization procedure applicable for ab initio and semiempirical linear combination of atomic orbital wave functions. The Journal of Chemical Physics, 90, 4916. https://doi.org/10.1063/1.456588
- Prashanth, J., Ramesh, G., Naik, J., Ojha, J., Reddy, B., Rao, G. (2015). Molecular structure, vibrational analysis and first order hyperpolarizability of 4-Methyl-3-Nitrobenzoic Acid using density functional theory. Optics and Photonics Journal, 5, 91-107. https://doi.org/10.4236/opj.2015.53008
- Prior, R.L., Hoang, H., Gu, L., Wu, X., Bacchocca, M., Howard, L., Hampsch-Woodill, M., Huang, D., Ou, B., Jacob, R. (2003). Assays for hydrophilic and lipophilic antioxidant capacity (oxygen radical absorbance capacity (ORACFL)) of plasma and other biological and food samples. J. Agric. Food. Chem., 51, 3273-3279. https://doi.org/10.1021/jf0262256
- Ramnath, S. (2017). Synthesis of copper nanoparticles from bee propolis extract and its antibacterial property. European J. Pharm. Med. Res., 4, 684-688.
- Santhoshkumar, J., Venkat, Kumar, S., Rajeshkumar, S. (2017). Synthesis of zinc oxide nanoparticles using plant leaf extract against urinary tract infection pathogen. Resource- Efficient Technologies, 3(4), 459-465. https://doi.org/10.1016/j.reffit.2017.05.001
- Scrocco, E., Tomasi, J. (1978). Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials. Advances in Quantum Chemistry, 11, 115–121. https://doi.org/10.1016/S0065-3276(08)60236-1
- Siddiquee, M.A., Ud din Parray, M., Mehdi, S.H., Alzahrani, K.A., Alshehri, A.A., Malik, M.A., Patel, R. (2020). Green synthesis of silver nanoparticles from delonix regia leaf extracts: in-vitro cytotoxicity and interaction studies with bovine serum albumin. Materials Chemistry and Physics, 242, 122493. https://doi.org/10.1016/j.matchemphys.2019.122493
- Singleton, V.L., & Rossi, J.A. (1965) Colorimetry of Total Phenolics with Phosphomolybdic-Phosphotungstic Acid Reagent. American Journal of Enology and Viticulture, 16, 144-158.
- Singleton, V.L., Orthofer, R., Lamuela-Raventos, R.M. (1999). Analysis of total phenols and other oxidation substrates and antioxidants by means of folin-ciocalteu reagent. Methods in Enzymology, 299, 152-178. http://dx.doi.org/10.1016/S0076-6879(99)99017-1
- Slinkard, K., Singleton, V.L. (1977). Total phenol analysis: automation and comparison with manual methods. American Journal of Enology and Viticulture, 28(1), 49-55.
- Stevens, J. (2017). Virtually going green: The role of quantum computational chemistry in reducing pollution and toxicity in chemistry. Physical Sciences Reviews, 2(7), 20170005. https://doi.org/10.1515/psr-2017-0005
- Tejamaya, M., Roemer, I., Merrifield, R.C., Lead, J.R. (2012). Stability of citrate, PVP, and PEG coated silver nanoparticles in ecotoxicology media. Environ. Sci. Technol., 46, 7011-7017. https://doi.org/10.1021/es2038596
- Trindle, C., Crum, P., Douglass, K. (2003). G2(MP2) Characterization of Conformational Preferences in 2-Substituted Ethanols (XCH2CH2OH) and Related Systems. J. Phys. Chem. A, 107, 6236. https://doi.org/10.1021/jp034598j
- Tsipis, A.C. (2014). DFT flavor of coordination chemistry. Coordination Chemistry Reviews, 272, 1–29. https://doi.org/10.1016/j.ccr.2014.02.023
- Van Mourik, T., Bühl, M., Gaigeot, M.P. (2014). Density functional theory across chemistry, physics, and biology. Philosophical Transactions of the Royal Society A., 372, 20120488. https://doi.org/10.1098/rsta.2012.0488
- Velammal, S.P., Devi, T.A., Amaladhas, T.P. (2016). Antioxidant, antimicrobial and cytotoxic activities of silver and gold nanoparticles synthesized using Plumbago zeylanica bark. Journal of Nanostructure in Chemistry, 6, 247-260. https://doi.org/10.1007/s40097-016-0198-x
- Weinhold, F. (1998). Natural Bond Orbital Methods In: Encyclopedia of Computational Chemistry 3, John Wiley and Sons.