Theoretical study of cellobiose hydrolysis to glucose in ionic liquids

Yoshifumi Nishimura; Daisuke Yokogawa; Stephan Irle

doi:10.1016/j.cplett.2014.04.014

Theoretical study of cellobiose hydrolysis to glucose in ionic liquids

Yoshifumi Nishimura
, Daisuke Yokogawa
, Stephan Irle

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

The S_N1-type hydrolysis reaction of cellobiose in ionic liquids (ILs) was theoretically investigated. First principles and ab initio quantum chemical methods were used in conjunction with the 'reference interaction site model self-consistent field with spatial electron density distribution' (RISM-SCF-SEDD) method. Reaction mechanism pathways are discussed and compared to calculations in gas phase and in aqueous solution. Analysis of solvation effects indicates strong interaction between hydrogen atoms of glucose hydroxyl groups and the anions in ILs, contributing to large stabilization of the reaction product. The calculated activation energy in ILs (24.5 kcal/mol) agrees quantitatively with the experimental value (26.5 kcal/mol).

Original language	English
Pages (from-to)	75-81
Number of pages	7
Journal	Chemical Physics Letters
Volume	603
DOIs	https://doi.org/10.1016/j.cplett.2014.04.014
State	Published - May 30 2014
Externally published	Yes

Funding

The work was funded by the Swedish Foundation for Strategic Research Framework Program RMA11–0037, the Formas project 229–2009-772, and the Swedish Research Council project 2010–4041. The authors also gratefully acknowledge the funding from the Knut and Alice Wallenberg Foundation and the Swedish Research Council for the advanced transmission electron microscopes and the Knut and Alice Wallenberg Foundation for their support of the -fab cleanroom infrastructure in Sweden.

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10.1016/j.cplett.2014.04.014

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title = "Theoretical study of cellobiose hydrolysis to glucose in ionic liquids",

abstract = "The SN1-type hydrolysis reaction of cellobiose in ionic liquids (ILs) was theoretically investigated. First principles and ab initio quantum chemical methods were used in conjunction with the 'reference interaction site model self-consistent field with spatial electron density distribution' (RISM-SCF-SEDD) method. Reaction mechanism pathways are discussed and compared to calculations in gas phase and in aqueous solution. Analysis of solvation effects indicates strong interaction between hydrogen atoms of glucose hydroxyl groups and the anions in ILs, contributing to large stabilization of the reaction product. The calculated activation energy in ILs (24.5 kcal/mol) agrees quantitatively with the experimental value (26.5 kcal/mol).",

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AU - Nishimura, Yoshifumi

AU - Yokogawa, Daisuke

AU - Irle, Stephan

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N2 - The SN1-type hydrolysis reaction of cellobiose in ionic liquids (ILs) was theoretically investigated. First principles and ab initio quantum chemical methods were used in conjunction with the 'reference interaction site model self-consistent field with spatial electron density distribution' (RISM-SCF-SEDD) method. Reaction mechanism pathways are discussed and compared to calculations in gas phase and in aqueous solution. Analysis of solvation effects indicates strong interaction between hydrogen atoms of glucose hydroxyl groups and the anions in ILs, contributing to large stabilization of the reaction product. The calculated activation energy in ILs (24.5 kcal/mol) agrees quantitatively with the experimental value (26.5 kcal/mol).

AB - The SN1-type hydrolysis reaction of cellobiose in ionic liquids (ILs) was theoretically investigated. First principles and ab initio quantum chemical methods were used in conjunction with the 'reference interaction site model self-consistent field with spatial electron density distribution' (RISM-SCF-SEDD) method. Reaction mechanism pathways are discussed and compared to calculations in gas phase and in aqueous solution. Analysis of solvation effects indicates strong interaction between hydrogen atoms of glucose hydroxyl groups and the anions in ILs, contributing to large stabilization of the reaction product. The calculated activation energy in ILs (24.5 kcal/mol) agrees quantitatively with the experimental value (26.5 kcal/mol).

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VL - 603

SP - 75

EP - 81

JO - Chemical Physics Letters

JF - Chemical Physics Letters

ER -

Theoretical study of cellobiose hydrolysis to glucose in ionic liquids

Abstract

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