Density Functional Theory Study of Intermolecular Interactions between Amylum and Cellulose

Raynardthan Pontoh; Vania Edita Rarisavitri; Christine Charen Yang; Maximilliam Febriand Putra; Daru Seto Bagus Anugrah

doi:10.22146/ijc.69241

Density Functional Theory Study of Intermolecular Interactions between Amylum and Cellulose

https://doi.org/10.22146/ijc.69241

Raynardthan Pontoh⁽¹⁾, Vania Edita Rarisavitri⁽²⁾, Christine Charen Yang⁽³⁾, Maximilliam Febriand Putra⁽⁴⁾, Daru Seto Bagus Anugrah^(5*)

(1) Undergraduate Program, Biotechnology Study Program, Faculty of Biotechnology, Atma Jaya Catholic University of Indonesia, BSD Campus, Tangerang 15345, Indonesia
(2) Undergraduate Program, Biotechnology Study Program, Faculty of Biotechnology, Atma Jaya Catholic University of Indonesia, BSD Campus, Tangerang 15345, Indonesia
(3) Undergraduate Program, Biotechnology Study Program, Faculty of Biotechnology, Atma Jaya Catholic University of Indonesia, BSD Campus, Tangerang 15345, Indonesia
(4) Undergraduate Program, Food Technology Study Program, Faculty of Biotechnology, Atma Jaya Catholic University of Indonesia, BSD Campus, Tangerang 15345, Indonesia
(5) Undergraduate Program, Biotechnology Study Program, Faculty of Biotechnology, Atma Jaya Catholic University of Indonesia, BSD Campus, Tangerang 15345, Indonesia
(*) Corresponding Author

Abstract

Amylum is one of the polysaccharides developed into biodegradable plastic bags. However, amylum-based plastics are easily damaged due to their low mechanical strength and hydrophilic properties. Cellulose is used as a support material in amylum-based plastics to increase strength and reduce water damage. This study investigated the molecular interactions between amylum and cellulose computationally. The minimum interaction energy of amylum and cellulose was calculated using in silico modeling using the Density Functional Theory (DFT) method. The B3LYP function and the basis set 6-31++g** were used in the calculations. Simultaneously, D3 Grimme dispersion correction was used as the effect of water solvent in the measures. The results obtained from this study were the interaction energy of amylum and cellulose of –29.8 kcal/mol. The HOMO-LUMO energy gap of the cellulose-amylum complex was lower than cellulose, indicating that the cellulose-amylum complex was more reactive and bonded to each other. Analysis of Natural Bond Orbital (NBO), Quantum Theory Atom in Molecule (QTAIM), Reduced Density Gradient (RDG), Non-covalent Interaction Index (NCI), and Intrinsic Bond Strength Index (IBSI) showed that the cellulose-amylum complex had weak to medium intermolecular bonds. The hydrogen bond at O61···H48 was the strongest in the complex. All data show that cellulose and amylum could interact through non-covalent bonds.

Keywords

amylum; DFT; cellulose; computational chemistry; intermolecular bonds

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References

[1] Sahin, H.T., and Arslan, M.B., 2008, A study on physical and chemical properties of cellulose paper immersed in various solvent mixtures, Int. J. Mol. Sci., 9 (1), 78–88.

[2] Anugrah, D.S.B., Alexander, H., Pramitasari, R., Hudiyanti, D., and Sagita, C.P., 2020, A review of polysaccharide-zinc oxide nanocomposites as safe coating for fruits preservation, Coatings, 10 (10) 988.

[3] Bauer, C.A., Schneider, G., and Göller, A.H., 2019, Machine learning models for hydrogen bond donor and acceptor strengths using large and diverse training data generated by first-principles interaction free energies, J. Cheminf., 11 (1), 59.

[4] Osman, A.F., Ashafee, A.M.T.L., Adnan, S.A., and Alakrach, A., 2020, Influence of hybrid cellulose/bentonite fillers on structure, ambient, and low temperature tensile properties of thermoplastic starch composites, Polym. Eng. Sci., 60 (4), 810–822.

[5] Ketema, A., and Worku, A., 2020, Review on intermolecular forces between dyes used for polyester dyeing and polyester fiber, J. Chem., 2020, 6628404.

[6] Cai, W., Xiao, C., Qian, L., and Cui, S., 2019, Detecting van der Waals forces between a single polymer repeating unit and a solid surface in high vacuum, Nano Res., 12 (1), 57–61.

[7] Dong, M., Miao, K., Hu, Y., Wu, J., Li, J., Pang, P., Miao, X., and Deng, W., 2017, Cooperating dipole-dipole and van der Waals interactions driven 2D self-assembly of fluorenone derivatives: Ester chain length effect, Phys. Chem. Chem. Phys., 19 (46), 31113–31120.

[8] Santana, R.F., Bonomo, R.C.F., Gandolfi, O.R.R., Rodrigues, L.B., Santos, L.S., dos Santos Pires, A.C., de Oliveira, C.P., da Costa Ilhéu Fontan, R., and Veloso, C.M., 2018, Characterization of starch-based bioplastics from jackfruit seed plasticized with glycerol, J. Food Sci. Technol., 55 (1), 278–286.

[9] Hudiyanti, D., Hamidi, N.I., Anugrah, D.S.B., Salimah, S.N.M., and Siahaan, P., 2019, Encapsulation of vitamin C in sesame liposomes: computational and experimental studies, Open Chem., 17 (1), 537–543.

[10] Agustin, M.B., Ahmmad, B., Alonzo, S.M.M., and Patriana, F.M., 2014, Bioplastic Based on Starch and Cellulose Nanocrystals from Rice Straw, J. Reinf. Plast. Compos., 33 (24), 2205–2213.

[11] Rahmawati, S., Radiman, C.L., and Martoprawiro, M.A., 2018, Density functional theory (DFT) and natural bond orbital (NBO) analysis of intermolecular hydrogen bond interaction in "Phosphorylated nata de coco - water", Indones. J. Chem., 18 (1), 173–178.

[12] Costa, M.P.M., Prates, L.M., Baptista, L., Cruz, M.T.M., and Ferreira, I.L.M., 2018, Interaction of polyelectrolyte complex between sodium alginate and chitosan dimers with a single glyphosate molecule: A DFT and NBO study, Carbohydr. Polym., 198, 51–60.

[13] Hammami, F., Ghalla, H., and Nasr, S., 2015, Intermolecular hydrogen bonds in urea-water complexes: DFT, NBO, and AIM analysis, Comput. Theor. Chem., 1070, 40–47.

[14] Deka, B.C., and Bhattacharyya, P.K., 2017, DFT study on host-guest interaction in chitosan–amino acid complexes, Comput. Theor. Chem., 1110, 40–49.

[15] Cortes, E., Márquez, E., Mora, J.R., Puello, E., Rangel, N., De Moya, A., and Trilleras, J., 2019, Theoretical study of the adsorption process of antimalarial drugs into acrylamide-base hydrogel model using DFT methods: The first approach to the rational design of a controlled drug delivery system, Processes, 7 (7), 396.

[16] Uto, T., and Yui, T., 2018, DFT optimization of isolated molecular chain sheet models constituting native cellulose crystal structures, ACS Omega, 3 (7), 8050–8058.

[17] Junxi, L., Qiong, S., Yamin, Z., and Yanbin, W., 2016, Theoretical insights into three types of oxidized starch-based adhesives: Chemical stability, water resistance, and shearing viscosity from a molecular viewpoint, J. Chem., 2016, 2369739.

[18] Goerigk, L., 2014, How do DFT-DCP, DFT-NL, and DFT-D3 compare for the description of London-dispersion effects in conformers and general thermochemistry?, J. Chem. Theory Comput., 10 (3), 968–980.

[19] Grimme, S., Antony, J., Ehrlich, S., and Krieg, H., 2010, A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu, J. Chem. Phys., 132, 154104.

[20] Valiev, M., Bylaska, E.J., Govind, N., Kowalski, K., Straatsma, T.P., Van Dam, H.J.J., Wang, D., Nieplocha, J., Apra, E., Windus, T.L., and de Jong, W.A., 2010, NWChem: A comprehensive and scalable open-source solution for large scale molecular simulations, Comput. Phys. Commun., 181 (9), 1477–1489.

[21] Anugrah, D.S.B., Darmalim, L.V., Putro, P.A., Nuratikah, L.D., Sasongko, N.A., Siahaan, P., and Yulandi, A., 2021, Computational evaluation of intermolecular interaction in poly(styrene-maleic acid)-water complexes using density functional theory, Indones. J. Chem., 21 (6) 1537–1549.

[22] Lu, T., and Chen, F., 2012, Multiwfn: A multifunctional wavefunction analyzer, J. Comput. Chem., 33 (5), 580–592.

[23] Hidayat, Y., Armunanto, R., and Pranowo, H.D., 2018, QMCF-MD simulation and NBO analysis of K(I) ion in liquid ammonia, Indones. J. Chem., 18 (2), 203–210.

[24] Martins, J.B.L., Quintino, R.P., Politi, J.R.S., Sethio, D., Gargano, R., and Kraka, E., 2020, Computational analysis of vibrational frequencies and rovibrational spectroscopic constants of hydrogen sulfide dimer using MP2 and CCSD(T), Spectrochim. Acta, Part A, 239, 118540.

[25] Garces, V., García-Quintero, A., Lerma, T.A., Palencia, M., Combatt, E.M., and Arrieta, Á.A., 2021, Characterization of cassava starch and its structural changes resulting of thermal stress by functionally-enhanced derivative spectroscopy (FEDS), Polysaccharides, 2 (4), 866–877.

[26] Siahaan, P., Sasongko, N.A., Lusiana, R.A., Prasasty, V.D., and Martoprawiro, M.A., 2021, The validation of molecular interaction among dimer chitosan with urea and creatinine using density functional theory: In application for hemodyalisis membrane, Int. J. Biol. Macromol., 168, 339–349.

[27] Miar, M., Shiroudi, A., Pourshamsian, K., Oliaey, A.R., and Hatamjafari, F., 2021, Theoretical investigations on the HOMO–LUMO gap and global reactivity descriptor studies, natural bond orbital, and nucleus-independent chemical shifts analyses of 3-phenylbenzo[d]thiazole-2(3H)-imine and its para-substituted derivatives: Solvent and subs, J. Chem. Res., 45 (1-2), 147–158.

[28] Shabani, M., Ghiasi, R., Zare, K., and Fazaeli, R., 2020, Quantum chemical study of interaction between titanocene dichloride anticancer drug and Al₁₂N₁₂ nano-cluster, Russ. J. Inorg. Chem., 65 (11), 1726–1734.

[29] Ghiasi, R., Emami, R., and Vasfi Sofiyani, M., 2021, Interaction between carboplatin with B₁₂P₁₂ and Al₁₂P₁₂ nano-clusters: A computational investigation, Phosphorus, Sulfur Silicon Relat. Elem., 196 (8), 751–759.

[30] Klein, J., Khartabil, H., Boisson, J.C., Contreras-Garciá, J., Piquemal, J.P., and Hénon, E., 2020, New way for probing bond strength, J. Phys. Chem. A, 124 (9), 1850–1860.

[31] Lefebvre, C., Khartabil, H., Boisson, J.C., Contreras-García, J., Piquemal, J.P., and Hénon, E., 2018, The independent gradient model: A new approach for probing strong and weak interactions in molecules from wave function calculations, ChemPhysChem, 19 (6), 724–735.

[32] Jabłoński, M., 2020, A critical overview of current theoretical methods of estimating the energy of intramolecular interactions, Molecules, 25 (23), 5512.

[33] Rodrigues-Oliveira, A.F., Ribeiro, F.W.M., Cervi, G., and Correra, T.C., 2018, Evaluation of common theoretical methods for predicting infrared multiphotonic dissociation vibrational spectra of intramolecular hydrogen-bonded ions, ACS Omega, 3 (8), 9075–9085.

[34] Granda, L.A., Oliver-Ortega, H., Fabra, M.J., Tarrés, Q., Pèlach, M.À., Lagarón, J.M., and Méndez, J.A., 2020, Improved process to obtain nanofibrillated cellulose (CNF) reinforced starch films with upgraded mechanical properties and barrier character, Polymers, 12 (5), 1071.

DOI: https://doi.org/10.22146/ijc.69241