The sulfonic acid-functionalized ionic liquids with pyridinium cations: Acidities and their acidity-catalytic activity relationships

Huabin Xing; Tao Wang; Zhenhuan Zhou; Youyuan Dai

doi:10.1016/j.molcata.2006.08.080

The sulfonic acid-functionalized ionic liquids with pyridinium cations: Acidities and their acidity-catalytic activity relationships

Huabin Xing, Tao Wang^*, Zhenhuan Zhou, Youyuan Dai

^*Corresponding author for this work

Tsinghua University

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

182 Citations (Scopus)

Abstract

The Brønsted acidities of sulfonic acid-functionalized ionic liquids (SFILs) with pyridinium cations were investigated. The Hammett function values of SFILs are between -1.5 and -3.6 at 110 °C. The acidities of SFILs depend on the anions, and have the order as follows: [PSPy][BF₄] > [PSPy][HSO₄] > [PSPy][pTSA] > [PSPy][H₂PO₄] ([PSPy] = N-propane-sulfonic acid pyridinium). The acidity order of SFILs is consistent with their activity order observed in some acid-catalyzed reactions. The minimum-energy geometries of SFILs manifest that anions have strong interactions with the sulfonic acid proton. It is considered that in addition to the alkyl sulfonic acid group, the anion is likely to serve as available acid sites. Hence the acidities and catalytic activities of SFILs depend on the kinds of anions.

Original language	English
Pages (from-to)	53-59
Number of pages	7
Journal	Journal of Molecular Catalysis A: Chemical
Volume	264
Issue number	1-2
DOIs	https://doi.org/10.1016/j.molcata.2006.08.080
Publication status	Published - 1 Mar 2007
Externally published	Yes

Keywords

Ab initio calculation
Brønsted acidity
Pyridinium cation
Sulfonic acid-functionalized ionic liquid

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10.1016/j.molcata.2006.08.080

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title = "The sulfonic acid-functionalized ionic liquids with pyridinium cations: Acidities and their acidity-catalytic activity relationships",

abstract = "The Br{\o}nsted acidities of sulfonic acid-functionalized ionic liquids (SFILs) with pyridinium cations were investigated. The Hammett function values of SFILs are between -1.5 and -3.6 at 110 °C. The acidities of SFILs depend on the anions, and have the order as follows: [PSPy][BF4] > [PSPy][HSO4] > [PSPy][pTSA] > [PSPy][H2PO4] ([PSPy] = N-propane-sulfonic acid pyridinium). The acidity order of SFILs is consistent with their activity order observed in some acid-catalyzed reactions. The minimum-energy geometries of SFILs manifest that anions have strong interactions with the sulfonic acid proton. It is considered that in addition to the alkyl sulfonic acid group, the anion is likely to serve as available acid sites. Hence the acidities and catalytic activities of SFILs depend on the kinds of anions.",

keywords = "Ab initio calculation, Br{\o}nsted acidity, Pyridinium cation, Sulfonic acid-functionalized ionic liquid",

author = "Huabin Xing and Tao Wang and Zhenhuan Zhou and Youyuan Dai",

year = "2007",

month = mar,

day = "1",

doi = "10.1016/j.molcata.2006.08.080",

language = "English",

volume = "264",

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journal = "Journal of Molecular Catalysis A: Chemical",

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TY - JOUR

T1 - The sulfonic acid-functionalized ionic liquids with pyridinium cations

T2 - Acidities and their acidity-catalytic activity relationships

AU - Xing, Huabin

AU - Wang, Tao

AU - Zhou, Zhenhuan

AU - Dai, Youyuan

PY - 2007/3/1

Y1 - 2007/3/1

N2 - The Brønsted acidities of sulfonic acid-functionalized ionic liquids (SFILs) with pyridinium cations were investigated. The Hammett function values of SFILs are between -1.5 and -3.6 at 110 °C. The acidities of SFILs depend on the anions, and have the order as follows: [PSPy][BF4] > [PSPy][HSO4] > [PSPy][pTSA] > [PSPy][H2PO4] ([PSPy] = N-propane-sulfonic acid pyridinium). The acidity order of SFILs is consistent with their activity order observed in some acid-catalyzed reactions. The minimum-energy geometries of SFILs manifest that anions have strong interactions with the sulfonic acid proton. It is considered that in addition to the alkyl sulfonic acid group, the anion is likely to serve as available acid sites. Hence the acidities and catalytic activities of SFILs depend on the kinds of anions.

AB - The Brønsted acidities of sulfonic acid-functionalized ionic liquids (SFILs) with pyridinium cations were investigated. The Hammett function values of SFILs are between -1.5 and -3.6 at 110 °C. The acidities of SFILs depend on the anions, and have the order as follows: [PSPy][BF4] > [PSPy][HSO4] > [PSPy][pTSA] > [PSPy][H2PO4] ([PSPy] = N-propane-sulfonic acid pyridinium). The acidity order of SFILs is consistent with their activity order observed in some acid-catalyzed reactions. The minimum-energy geometries of SFILs manifest that anions have strong interactions with the sulfonic acid proton. It is considered that in addition to the alkyl sulfonic acid group, the anion is likely to serve as available acid sites. Hence the acidities and catalytic activities of SFILs depend on the kinds of anions.

KW - Ab initio calculation

KW - Brønsted acidity

KW - Pyridinium cation

KW - Sulfonic acid-functionalized ionic liquid

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U2 - 10.1016/j.molcata.2006.08.080

DO - 10.1016/j.molcata.2006.08.080

M3 - Article

AN - SCOPUS:33847290523

SN - 1381-1169

VL - 264

SP - 53

EP - 59

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

IS - 1-2

ER -

The sulfonic acid-functionalized ionic liquids with pyridinium cations: Acidities and their acidity-catalytic activity relationships

Abstract

Keywords

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