Effect of structure of large aromatic molecules grafted onto cellulose on hydrolysis of the glycosidic linkages

David Karst, Yiqi Yang

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Molecular modeling is used to explain how grafting various molecules that contain large aromatic structures and different reactive groups onto cellulose dramatically increases the hydrolysis of the glycosidic linkages of cellulose. Hydrolysis is found to increase with the increasing size of the molecule grafted to cellulose, and experiments support this finding. A larger substituent on cellulose increases hydrolysis by causing the hydrolyzed cellulose structure to be more stable compared to hydrolyzed cellulose grafted to a smaller substituent. A larger substituent forms stronger interactions with cellulose and has a greater ability to reduce the mobility of the cleaved cellulose chain to which it is bonded, which allows the cleaved cellulose to form stronger cellulosecellulose interactions after hydrolysis. A substituent on the C6 position of cellulose increases hydrolysis to a greater extent than does the same substituent on the C 3 or C2 position.

Original languageEnglish (US)
Pages (from-to)784-791
Number of pages8
JournalMacromolecular Chemistry and Physics
Volume208
Issue number7
DOIs
StatePublished - Apr 3 2007

Keywords

  • Biopolymers
  • Cellulose
  • Dyes/pigments
  • Hydrolysis
  • Molecular modeling

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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