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Interactions of Cellulose Model Compound D‐Cellobiose with Selected Metal Chlorides in Water: Identification of Chelating Oxygen Atoms
Author(s) -
Fernando Harshica,
Amarasekara Ananda S.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100972
Subject(s) - cellobiose , chemistry , cellulose , metal , oxygen , chelation , chloride , metal ions in aqueous solution , inorganic chemistry , organic chemistry , cellulase
Understanding interactions of metal ions with cellulose is an important step in the development of efficient catalytic methods for processing cellulose. In this study, density functional theory methods were used to identify oxygen atoms interacting or chelating with selected metal chlorides of Li + , K + , Mg 2+ , Ca 2+ , Sn 2+ , Zn 2+ and La 3+ with cellulose model compound D‐cellobiose. Calculated metal‐oxygen distances of energy minimized D‐cellobiose : metal chloride 1 : 2 mixtures revealed that the metal ions approach between the two glucose rings in α/β‐D‐cellobiose, and O 4 , O 9 are the preferred interaction/chelation points. DFT study supported a previous 13 C NMR chemical shift change based experiments. ZnCl 2 showing the shortest metal‐oxygen distances in approach to α/β D‐cellobiose is known to produce the largest 13 C NMR chemical shift changes in D‐cellobiose. In α‐anomer, average closest metal‐oxygen distances and NMR shift changes co‐related at 95 % confidence interval with liner regression R 2 =0.8582 and Sy.x=0.5722.