Nitrile functionalized methimazole-based ionic liquids

Amal I. Siriwardana; Angel A.J. Torriero; Juan M. Reyna-González; Iko M. Burgar; Noel F. Dunlop; Alan M. Bond; Glen B. Deacon; Douglas R. MacFarlane

doi:10.1021/jo101449q

Nitrile functionalized methimazole-based ionic liquids

Amal I. Siriwardana
, Angel A.J. Torriero
, Juan M. Reyna-González
, Iko M. Burgar
, Noel F. Dunlop
, Alan M. Bond
, Glen B. Deacon
, Douglas R. MacFarlane

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

22 Citations (Scopus)

Abstract

The alkylation reaction of 2-mercapto-1-methylimidazole 1b with 2-chloroacetonitrile and 2-chloropropionitrile produced S-alkyl methimazole chlorides 2a and 2b which were subjected to anion metathesis with lithium bis(trifluoromethanesulfonyl)amide, LiNTf₂, to afford nitrile functionalized methimazole-based room temperature ionic liquids 3a and 3b in 94% and 89% yields, respectively. Ionic liquids 3a and 3b have reasonably wide electrochemical windows. The efficient extraction of Ag⁺ from aqueous media into 3a and 3b is also reported.

Original language	English
Pages (from-to)	8376-8382
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	75
Issue number	24
DOIs	https://doi.org/10.1021/jo101449q
Publication status	Published - 17 Dec 2010
Externally published	Yes

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10.1021/jo101449q

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title = "Nitrile functionalized methimazole-based ionic liquids",

abstract = "The alkylation reaction of 2-mercapto-1-methylimidazole 1b with 2-chloroacetonitrile and 2-chloropropionitrile produced S-alkyl methimazole chlorides 2a and 2b which were subjected to anion metathesis with lithium bis(trifluoromethanesulfonyl)amide, LiNTf2, to afford nitrile functionalized methimazole-based room temperature ionic liquids 3a and 3b in 94\% and 89\% yields, respectively. Ionic liquids 3a and 3b have reasonably wide electrochemical windows. The efficient extraction of Ag+ from aqueous media into 3a and 3b is also reported.",

author = "Siriwardana, \{Amal I.\} and Torriero, \{Angel A.J.\} and Reyna-Gonz{\'a}lez, \{Juan M.\} and Burgar, \{Iko M.\} and Dunlop, \{Noel F.\} and Bond, \{Alan M.\} and Deacon, \{Glen B.\} and MacFarlane, \{Douglas R.\}",

year = "2010",

month = dec,

day = "17",

doi = "10.1021/jo101449q",

language = "English",

volume = "75",

pages = "8376--8382",

journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Nitrile functionalized methimazole-based ionic liquids

AU - Siriwardana, Amal I.

AU - Torriero, Angel A.J.

AU - Reyna-González, Juan M.

AU - Burgar, Iko M.

AU - Dunlop, Noel F.

AU - Bond, Alan M.

AU - Deacon, Glen B.

AU - MacFarlane, Douglas R.

PY - 2010/12/17

Y1 - 2010/12/17

N2 - The alkylation reaction of 2-mercapto-1-methylimidazole 1b with 2-chloroacetonitrile and 2-chloropropionitrile produced S-alkyl methimazole chlorides 2a and 2b which were subjected to anion metathesis with lithium bis(trifluoromethanesulfonyl)amide, LiNTf2, to afford nitrile functionalized methimazole-based room temperature ionic liquids 3a and 3b in 94% and 89% yields, respectively. Ionic liquids 3a and 3b have reasonably wide electrochemical windows. The efficient extraction of Ag+ from aqueous media into 3a and 3b is also reported.

AB - The alkylation reaction of 2-mercapto-1-methylimidazole 1b with 2-chloroacetonitrile and 2-chloropropionitrile produced S-alkyl methimazole chlorides 2a and 2b which were subjected to anion metathesis with lithium bis(trifluoromethanesulfonyl)amide, LiNTf2, to afford nitrile functionalized methimazole-based room temperature ionic liquids 3a and 3b in 94% and 89% yields, respectively. Ionic liquids 3a and 3b have reasonably wide electrochemical windows. The efficient extraction of Ag+ from aqueous media into 3a and 3b is also reported.

UR - https://www.scopus.com/pages/publications/78650407226

U2 - 10.1021/jo101449q

DO - 10.1021/jo101449q

M3 - Article

AN - SCOPUS:78650407226

SN - 0022-3263

VL - 75

SP - 8376

EP - 8382

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

Nitrile functionalized methimazole-based ionic liquids

Abstract

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