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  The Electronic Nature of the 1,4-β-Glycosidic Bond and Its Chemical Environment: DFT Insights into Cellulose Chemistry

Loerbroks, C., Rinaldi, R., & Thiel, W. (2013). The Electronic Nature of the 1,4-β-Glycosidic Bond and Its Chemical Environment: DFT Insights into Cellulose Chemistry. Chemistry - A European Journal, 19(48), 16282-16294. doi:10.1002/chem.201301366.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0014-C998-5 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0014-C999-3
Genre: Journal Article

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chem_201301366_sm_miscellaneous_information-1.pdf (Supplementary material), 6MB
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chem_201301366_sm_miscellaneous_information-1.pdf
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Supporting Information
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Copyright Date:
2013
Copyright Info:
Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
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 Creators:
Loerbroks, Claudia1, Author              
Rinaldi, Roberto2, Author              
Thiel, Walter1, Author              
Affiliations:
1Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              
2Research Group Rinaldi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445617              

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Free keywords: cellobiose · cellulose hydrolysis · computational chemistry · density functional calculations · NBO analysis
 Abstract: The molecular understanding of the chemistry of 1,4-β-glucans is essential for designing new approaches to the conversion of cellulose into platform chemicals and biofuels. In this endeavor, much attention has been paid to the role of hydrogen bonding occurring in the cellulose structure. So far, however, there has been little discussion about the implications of the electronic nature of the 1,4-β-glycosidic bond and its chemical environment for the activation of 1,4-β-glucans toward acid-catalyzed hydrolysis. This report sheds light on these central issues and addresses their influence on the acid hydrolysis of cellobiose and, by analogy, cellulose. The electronic structure of cellobiose was explored by DFT at the BB1 K/6-31++G(d,p) level. Natural bond orbital (NBO) analysis was performed to grasp the key bonding concepts. Conformations, protonation sites, and hydrolysis mechanisms were examined. The results for cellobiose indicate that cellulose is protected against hydrolysis not only by its supramolecular structure, as currently accepted, but also by its electronic structure, in which the anomeric effect plays a key role.

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Language(s): eng - English
 Dates: 2013-08-132013-04-112013-10-182013-11-25
 Publication Status: Published in print
 Pages: 13
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201301366
 Degree: -

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Title: Chemistry - A European Journal
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: 13 Volume / Issue: 19 (48) Sequence Number: - Start / End Page: 16282 - 16294 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058