The first dehydration and the competing reaction pathways of glucose homogeneously and heterogeneously catalyzed by acids

Literature Information

Publication Date 2013-01-03
DOI 10.1039/C2CP43644B
Impact Factor 3.676
Authors

David Lee Phillips


View Original

Abstract

The dehydration mechanisms for glucose in β-pyranose (BP) and in open-chain (OC) forms, catalyzed by acids homogeneously and heterogeneously, were investigated using density functional and two-layer ONIOM calculations. The first dehydration reaction and competing reaction pathways are the main focus of the present study. The energetics of five dehydration and two isomerization pathways were examined for the protonated form of BP in acidic aqueous solutions and the most favorable pathway of these was found to be the dehydration at the anomeric site. No dehydration pathway of OC glucose is favored over its isomerization to BP or to fructose. The relative ease of dehydration over isomerization depends on the selection of the reaction media for the protonated form of BP. These two reaction pathways catalyzed by a surface Brönsted acid site were then examined and the isomerization pathway was found to be more favorable than dehydration at the anomeric site on a surface acid site. These mechanistic insights provide an important guide for the catalyst design/selection of the reaction media for glucose dehydration.

Related Literature

Selective CO2 capture in an imine linked porphyrin porous polymer

Venkata S. Pavan K. Neti, Xiaofei Wu, Shuguang Deng, Luis Echegoyen

2013-07-03 Communication

DOI: 10.1039/C3PY00798G

Porous films based on a conjugated polymergelator for fluorescent detection of explosive vapors

Xiaofu Wu, Hui Tong, Lixiang Wang

2013-07-16 Communication

DOI: 10.1039/C3PY00806A

Comparing solution and melt-state association of hydrogen bonds in supramolecular polymers

Florian Herbst, Wolfgang H. Binder

2013-04-19 Paper

DOI: 10.1039/C3PY00362K

Characterization and assembly investigation of a dodecapeptide hydrolyzed from the crystalline domain of Bombyx mori silk fibroin

Ruiwen Hao, Jinming Zhang, Tao Xu, Lei Huang, Jinrong Yao, Xin Chen, Zhengzhong Shao

2013-02-07 Paper

DOI: 10.1039/C3PY21096K

A new method to make polymers with flexible main chains and photoelectric pendants for organic semiconductors

Yeli Fan, Baoping Lin, Ying Sun, Xiaohui Gong, Hong Yang, Xueqin Zhang

2013-05-22 Paper

DOI: 10.1039/C3PY00454F

Synthesis of random copolymer based pH-responsive nanoparticles as drug carriers for cancer therapeutics

Apiradee Honglawan, Houping Ni, Drew Weissman

2013-05-08 Paper

DOI: 10.1039/C3PY00390F

Polymerization of methyl methacrylate by latent pre-catalysts based on CO2-protected N-heterocyclic carbenes

Stefan Naumann, Friedrich Georg Schmidt, Roman Schowner, Wolfgang Frey

2013-02-19 Paper

DOI: 10.1039/C3PY00073G

Contents list

2021-02-24 Front/Back Matter

DOI: 10.1039/C3PY90042H

High Tg thermosetting resins from resveratrol

Jessica J. Cash, Matthew C. Davis, Michael D. Ford, Thomas J. Groshens, Andrew J. Guenthner, Benjamin G. Harvey, Kevin R. Lamison, Joseph M. Mabry, Heather A. Meylemans, Josiah T. Reams, Christopher M. Sahagun

2013-04-26 Paper

DOI: 10.1039/C3PY00438D

You might also like

Compound Q&A

Is 6-(3-Fluorophenyl)picolinic acid (CAS: 887982-40-3) safe?

6-(3-Fluorophenyl)picolinic acid is generally considered safe for laboratory use...

887982-40-36-(3-Fluorophenyl)pi...
Compound Q&A

What industries use (3R)-3-Pyrrolidinol (CAS: 2799-21-5)?

(3R)-3-Pyrrolidinol is used in the pharmaceutical industry as a precursor for dr...

2799-21-5(3R)-3-Pyrrolidinol
Compound Q&A

What precautions should be taken when handling (4R,5R)-4,5-Diethoxycarbonyl-2,2-dimethyldioxolane (CAS: 59779-75-8)?

When handling (4R,5R)-4,5-Diethoxycarbonyl-2,2-dimethyldioxolane (CAS: 59779-75-...

59779-75-8(4R,5R)-4,5-Diethoxy...
Compound Q&A

How is 1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)ethanone (CAS: 90734-71-7) typically synthesized?

1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)ethanone is often synthesized via a mult...

90734-71-71-(6-Chloroimidazo[1...
Compound Q&A

What is the market or research trend for N-Ethyl-3,4-dimethylbenzylamine (CAS: 39180-83-1)?

The market for N-Ethyl-3,4-dimethylbenzylamine (CAS: 39180-83-1) remains steady,...

39180-83-1N-Ethyl-3,4-dimethyl...
Compound Q&A

What is Tert-butyl 3-(pyrrolidin-1-yl)azetidine-1-carboxylate (CAS: 1019008-21-9)?

Tert-butyl 3-(pyrrolidin-1-yl)azetidine-1-carboxylate is a chemical compound wit...

1019008-21-9Tert-butyl 3-(pyrrol...
Compound Q&A

What regulatory guidelines apply to 1-Bromo-3-chloro-2,4-dimethoxybenzene (CAS: 1228956-93-1)?

1-Bromo-3-chloro-2,4-dimethoxybenzene (CAS: 1228956-93-1) falls under the classi...

1228956-93-11-Bromo-3-chloro-2,4...
Compound Q&A

Is 8-Bromo-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (CAS: 1368622-07-4) safe?

The safety of 8-Bromo-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (CAS: 1368622-07...

1368622-07-48-Bromo-2-methyl-3,4...
Compound Q&A

Is Benzyl [(3S)-2,6-dioxo-3-piperidinyl]carbamate (CAS: 22785-43-9) safe?

Benzyl [(3S)-2,6-dioxo-3-piperidinyl]carbamate is generally safe when handled wi...

22785-43-9Benzyl [(3S)-2,6-dio...
Compound Q&A

How should 1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonyl}pyrrolidine (CAS: 928657-21-0) be stored?

1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonyl}pyrrolidine s...

928657-21-01-{[4-(4,4,5,5-Tetra...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.