Biopolymers have become more and more attractive nowadays for both experimental and theoretical studies because of their importance in our daily life. In this contribution, the electronic properties and reactivity behavior of some biomonomers; chitin and chitosan have been thoroughly investigated theoretically using density functional theory (DFT) B3LYP/6-31G(d) level of theory. The regioselectivity of these molecules has been rationalized by using both Fukui and Parr indices in order to explain and show the most probable sites to be attacked towards nucleophiles and electrophiles. For the three studied monomers, the oxygen and nitrogen atoms were found to be the most reactive sites. Parr functions and Fukui functions found to be complementary while explaining the possible regioselectivity.
Ravi Kumar, MNV. A review of chitin and chitosan applications. React. Funct. Polym. 2000, 46, 1–27.
Tao, Y.; Zhang, H.L.; Hu, Y.M. et al. Preparation of chitosan and water-soluble chitosan microspheres via spray-drying method to lower blood lipids in rats fed with high-fat diets. Int. J. Mol. Sci. 2013, 14 (2), 4174-4184.
Roberts, G.A.F. Preparation of chitin and chitosan. Chitin chemistry. Red Globe Press Press: London, 1992.
Chang, K.L.B.; Tsai, G.; Lee, J. et al. Heterogeneous N-deacetylation of chitin in alkaline solution. Carbohydr. Res. 1997, 303 (3), 327-332.
Araki, Y.; Ito, E. A pathway of chitosan formation in Mucor rouxii (enzymatic deacetylation of chitin). Eur. J. Biochem. 1975, 55(1), 71-78.
Usami, Y.; Minami, S.; Okamoto, Y. et al. Carbohydr. Polym. 1997, 32 (2), 115-122.
Peniche, C.; Argüelles-Monal, W.; Goycoolea, F.M. Chitin and chitosan: major sources, properties and applications. In Monomers, polymers and composites from renewable resources. Elsevier: 2008.
Ravi Kumar, MNV. A review of chitin and chitosan applications. React. Funct. Polym. 2000, 46, 1–27.
Tao, Y.; Zhang, H.L.; Hu, Y.M. et al. Preparation of chitosan and water-soluble chitosan microspheres via spray-drying method to lower blood lipids in rats fed with high-fat diets. Int. J. Mol. Sci. 2013, 14 (2), 4174-4184.
Roberts, G.A.F. Preparation of chitin and chitosan. Chitin chemistry. Red Globe Press Press: London, 1992.
Chang, K.L.B.; Tsai, G.; Lee, J. et al. Heterogeneous N-deacetylation of chitin in alkaline solution. Carbohydr. Res. 1997, 303 (3), 327-332.
Araki, Y.; Ito, E. A pathway of chitosan formation in Mucor rouxii (enzymatic deacetylation of chitin). Eur. J. Biochem. 1975, 55(1), 71-78.
Usami, Y.; Minami, S.; Okamoto, Y. et al. Carbohydr. Polym. 1997, 32 (2), 115-122.
Peniche, C.; Argüelles-Monal, W.; Goycoolea, F.M. Chitin and chitosan: major sources, properties and applications. In Monomers, polymers and composites from renewable resources. Elsevier: 2008.
Samir Benykhlef
Ecole Supérieure en Sciences Appliquées de Tlemcen, ESSA-Tlemcen, BP 165 RP Bel Horizon, Tlemcen 13000, Algeria0009-0000-3118-658XAlgeria
Messaoudı, B., & Benykhlef, S. (2024). Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan. International Journal of Chemistry and Technology, 8(2), 164-169. https://doi.org/10.32571/ijct.1491250
AMA
Messaoudı B, Benykhlef S. Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan. Int. J. Chem. Technol. December 2024;8(2):164-169. doi:10.32571/ijct.1491250
Chicago
Messaoudı, Boulanouar, and Samir Benykhlef. “Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan”. International Journal of Chemistry and Technology 8, no. 2 (December 2024): 164-69. https://doi.org/10.32571/ijct.1491250.
EndNote
Messaoudı B, Benykhlef S (December 1, 2024) Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan. International Journal of Chemistry and Technology 8 2 164–169.
IEEE
B. Messaoudı and S. Benykhlef, “Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan”, Int. J. Chem. Technol., vol. 8, no. 2, pp. 164–169, 2024, doi: 10.32571/ijct.1491250.
ISNAD
Messaoudı, Boulanouar - Benykhlef, Samir. “Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan”. International Journal of Chemistry and Technology 8/2 (December 2024), 164-169. https://doi.org/10.32571/ijct.1491250.
JAMA
Messaoudı B, Benykhlef S. Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan. Int. J. Chem. Technol. 2024;8:164–169.
MLA
Messaoudı, Boulanouar and Samir Benykhlef. “Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan”. International Journal of Chemistry and Technology, vol. 8, no. 2, 2024, pp. 164-9, doi:10.32571/ijct.1491250.
Vancouver
Messaoudı B, Benykhlef S. Theoretical Study of the Regioselectivity of Some Monomers: Chitin and Chitosan. Int. J. Chem. Technol. 2024;8(2):164-9.