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DFT and experimental analysis of aluminium chloride as a Lewis acid proton carrier catalyst for dimethyl carbonate carboxymethylation of alcohols

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DFT and experimental analysis of aluminium chloride as a Lewis acid proton carrier catalyst for dimethyl carbonate carboxymethylation of alcohols. / Jin, Saimeng; Tian, Yin; McElroy, Con Robert; Wang, Dongqi; Clark, James H.; Hunt, Andrew J.

In: Catalysis Science and Technology, Vol. 7, No. 20, 28.09.2017, p. 4859-4865.

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Harvard

Jin, S, Tian, Y, McElroy, CR, Wang, D, Clark, JH & Hunt, AJ 2017, 'DFT and experimental analysis of aluminium chloride as a Lewis acid proton carrier catalyst for dimethyl carbonate carboxymethylation of alcohols', Catalysis Science and Technology, vol. 7, no. 20, pp. 4859-4865. https://doi.org/10.1039/C7CY01190C, https://doi.org/10.1039/c7cy01190c

APA

Jin, S., Tian, Y., McElroy, C. R., Wang, D., Clark, J. H., & Hunt, A. J. (2017). DFT and experimental analysis of aluminium chloride as a Lewis acid proton carrier catalyst for dimethyl carbonate carboxymethylation of alcohols. Catalysis Science and Technology, 7(20), 4859-4865. https://doi.org/10.1039/C7CY01190C, https://doi.org/10.1039/c7cy01190c

Vancouver

Jin S, Tian Y, McElroy CR, Wang D, Clark JH, Hunt AJ. DFT and experimental analysis of aluminium chloride as a Lewis acid proton carrier catalyst for dimethyl carbonate carboxymethylation of alcohols. Catalysis Science and Technology. 2017 Sep 28;7(20):4859-4865. https://doi.org/10.1039/C7CY01190C, https://doi.org/10.1039/c7cy01190c

Author

Jin, Saimeng ; Tian, Yin ; McElroy, Con Robert ; Wang, Dongqi ; Clark, James H. ; Hunt, Andrew J. / DFT and experimental analysis of aluminium chloride as a Lewis acid proton carrier catalyst for dimethyl carbonate carboxymethylation of alcohols. In: Catalysis Science and Technology. 2017 ; Vol. 7, No. 20. pp. 4859-4865.

Bibtex - Download

@article{4300d8cd8bff46289b031864d0a345c6,
title = "DFT and experimental analysis of aluminium chloride as a Lewis acid proton carrier catalyst for dimethyl carbonate carboxymethylation of alcohols",
abstract = "The Lewis acid catalysed mechanism of dimethyl carbonate (DMC) mediated carboxymethylation of alcohol was investigated experimentally and through computational chemistry methods including density functional theory (DFT). Experimental data showed that catalytic loading of AlCl3 enabled the quantitative carboxymethylation of octanol in less than 20 h, while in the absence of a catalyst only trace product was observed. The geometry of the identified transition states and related energy barriers indicate that the activation energies in AlCl3 catalysed pathways are significantly lower than those in catalyst-free pathways. Theoretical quantum chemistry methods were utilised to explore and analyse the complex of DMC with AlCl3. Natural bond orbital theory analysis and molecular orbital analysis demonstrated that the dipole present in Al-Cl covalent bonding plays a vital role in assisting the proton-transfer process. Most importantly, the reaction mechanism disclosed in this research can aid in the exploration of new Lewis acid catalysed processes in the field of dialkyl carbonate chemistry.",
author = "Saimeng Jin and Yin Tian and McElroy, {Con Robert} and Dongqi Wang and Clark, {James H.} and Hunt, {Andrew J.}",
note = "{\textcopyright} The Royal Society of Chemistry 2017. This is an author-produced version of a paper accepted for publication. Uploaded with permission of the publisher/copyright holder. Further copying may not be permitted; contact the publisher for details",
year = "2017",
month = sep,
day = "28",
doi = "10.1039/C7CY01190C",
language = "English",
volume = "7",
pages = "4859--4865",
journal = "Catalysis Science and Technology",
issn = "2044-4753",
publisher = "Royal Society of Chemistry",
number = "20",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - DFT and experimental analysis of aluminium chloride as a Lewis acid proton carrier catalyst for dimethyl carbonate carboxymethylation of alcohols

AU - Jin, Saimeng

AU - Tian, Yin

AU - McElroy, Con Robert

AU - Wang, Dongqi

AU - Clark, James H.

AU - Hunt, Andrew J.

N1 - © The Royal Society of Chemistry 2017. This is an author-produced version of a paper accepted for publication. Uploaded with permission of the publisher/copyright holder. Further copying may not be permitted; contact the publisher for details

PY - 2017/9/28

Y1 - 2017/9/28

N2 - The Lewis acid catalysed mechanism of dimethyl carbonate (DMC) mediated carboxymethylation of alcohol was investigated experimentally and through computational chemistry methods including density functional theory (DFT). Experimental data showed that catalytic loading of AlCl3 enabled the quantitative carboxymethylation of octanol in less than 20 h, while in the absence of a catalyst only trace product was observed. The geometry of the identified transition states and related energy barriers indicate that the activation energies in AlCl3 catalysed pathways are significantly lower than those in catalyst-free pathways. Theoretical quantum chemistry methods were utilised to explore and analyse the complex of DMC with AlCl3. Natural bond orbital theory analysis and molecular orbital analysis demonstrated that the dipole present in Al-Cl covalent bonding plays a vital role in assisting the proton-transfer process. Most importantly, the reaction mechanism disclosed in this research can aid in the exploration of new Lewis acid catalysed processes in the field of dialkyl carbonate chemistry.

AB - The Lewis acid catalysed mechanism of dimethyl carbonate (DMC) mediated carboxymethylation of alcohol was investigated experimentally and through computational chemistry methods including density functional theory (DFT). Experimental data showed that catalytic loading of AlCl3 enabled the quantitative carboxymethylation of octanol in less than 20 h, while in the absence of a catalyst only trace product was observed. The geometry of the identified transition states and related energy barriers indicate that the activation energies in AlCl3 catalysed pathways are significantly lower than those in catalyst-free pathways. Theoretical quantum chemistry methods were utilised to explore and analyse the complex of DMC with AlCl3. Natural bond orbital theory analysis and molecular orbital analysis demonstrated that the dipole present in Al-Cl covalent bonding plays a vital role in assisting the proton-transfer process. Most importantly, the reaction mechanism disclosed in this research can aid in the exploration of new Lewis acid catalysed processes in the field of dialkyl carbonate chemistry.

UR - http://www.scopus.com/inward/record.url?scp=85031323204&partnerID=8YFLogxK

U2 - 10.1039/C7CY01190C

DO - 10.1039/C7CY01190C

M3 - Article

AN - SCOPUS:85031323204

VL - 7

SP - 4859

EP - 4865

JO - Catalysis Science and Technology

JF - Catalysis Science and Technology

SN - 2044-4753

IS - 20

ER -