Selective colorimetric assay of cyanide ions using a thioamide-based probe containing phenol and pyridyl groups

Eun Joo Song; Soojin Kim; Gyeong Jin Park; Sol Ji Park; Ye Won Choi; Cheal Kim; Jinheung Kim

doi:10.1016/j.tetlet.2014.09.049

Selective colorimetric assay of cyanide ions using a thioamide-based probe containing phenol and pyridyl groups

Eun Joo Song, Soojin Kim, Gyeong Jin Park, Sol Ji Park, Ye Won Choi, Cheal Kim, Jinheung Kim

Department of Chemistry & Nanoscience

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

6 Scopus citations

Abstract

The selective assay of cyanide ions with a thioamide compound (HNPTU) containing phenol and pyridine as a chemosensor is reported using absorbance changes in a buffered aqueous solution (50 mM HEPES, pH 7.4) containing ethanol. Upon treatment with cyanide ions, the colorless solution of HNPTU turned yellow. No significant changes were observed with other comparable anions, such as F^-, Cl^-, Br^-, I^-, and CH₃COO^-. The color change of HNPTU upon treatment with CN^- was maintained even in the presence of the comparable monovalent anions. The complex stability constant (K_a = 2.6 × 10³) for the stoichiometric 1:1 complexation of HNPTU with cyanide ions was obtained based on absorbance titrations. The interaction of HNPTU with cyanide ions was proposed to be deprotonation, as shown by NMR and Cu(II) treatment experiments.

Original language	English
Pages (from-to)	6965-6968
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2014.09.049
State	Published - 17 Dec 2014

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea Grant funded by the Korea Government ( NRF-2013R1A2A2A03015101 , 2012001725 , and 2012008875 ).

Publisher Copyright:
©2014 Elsevier B.V. All rights reserved.

Keywords

Colorimetric sensor
Cyanide ion
Deprotonation
Phenol
Pyridyl

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10.1016/j.tetlet.2014.09.049

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title = "Selective colorimetric assay of cyanide ions using a thioamide-based probe containing phenol and pyridyl groups",

abstract = "The selective assay of cyanide ions with a thioamide compound (HNPTU) containing phenol and pyridine as a chemosensor is reported using absorbance changes in a buffered aqueous solution (50 mM HEPES, pH 7.4) containing ethanol. Upon treatment with cyanide ions, the colorless solution of HNPTU turned yellow. No significant changes were observed with other comparable anions, such as F-, Cl-, Br-, I-, and CH3COO-. The color change of HNPTU upon treatment with CN- was maintained even in the presence of the comparable monovalent anions. The complex stability constant (Ka = 2.6 × 103) for the stoichiometric 1:1 complexation of HNPTU with cyanide ions was obtained based on absorbance titrations. The interaction of HNPTU with cyanide ions was proposed to be deprotonation, as shown by NMR and Cu(II) treatment experiments.",

keywords = "Colorimetric sensor, Cyanide ion, Deprotonation, Phenol, Pyridyl",

author = "Song, {Eun Joo} and Soojin Kim and Park, {Gyeong Jin} and Park, {Sol Ji} and Choi, {Ye Won} and Cheal Kim and Jinheung Kim",

note = "Funding Information: This work was supported by the National Research Foundation of Korea Grant funded by the Korea Government ( NRF-2013R1A2A2A03015101 , 2012001725 , and 2012008875 ). Publisher Copyright: {\textcopyright}2014 Elsevier B.V. All rights reserved.",

year = "2014",

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doi = "10.1016/j.tetlet.2014.09.049",

language = "English",

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pages = "6965--6968",

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T1 - Selective colorimetric assay of cyanide ions using a thioamide-based probe containing phenol and pyridyl groups

AU - Song, Eun Joo

AU - Kim, Soojin

AU - Park, Gyeong Jin

AU - Park, Sol Ji

AU - Choi, Ye Won

AU - Kim, Cheal

AU - Kim, Jinheung

N1 - Funding Information: This work was supported by the National Research Foundation of Korea Grant funded by the Korea Government ( NRF-2013R1A2A2A03015101 , 2012001725 , and 2012008875 ). Publisher Copyright: ©2014 Elsevier B.V. All rights reserved.

PY - 2014/12/17

Y1 - 2014/12/17

N2 - The selective assay of cyanide ions with a thioamide compound (HNPTU) containing phenol and pyridine as a chemosensor is reported using absorbance changes in a buffered aqueous solution (50 mM HEPES, pH 7.4) containing ethanol. Upon treatment with cyanide ions, the colorless solution of HNPTU turned yellow. No significant changes were observed with other comparable anions, such as F-, Cl-, Br-, I-, and CH3COO-. The color change of HNPTU upon treatment with CN- was maintained even in the presence of the comparable monovalent anions. The complex stability constant (Ka = 2.6 × 103) for the stoichiometric 1:1 complexation of HNPTU with cyanide ions was obtained based on absorbance titrations. The interaction of HNPTU with cyanide ions was proposed to be deprotonation, as shown by NMR and Cu(II) treatment experiments.

AB - The selective assay of cyanide ions with a thioamide compound (HNPTU) containing phenol and pyridine as a chemosensor is reported using absorbance changes in a buffered aqueous solution (50 mM HEPES, pH 7.4) containing ethanol. Upon treatment with cyanide ions, the colorless solution of HNPTU turned yellow. No significant changes were observed with other comparable anions, such as F-, Cl-, Br-, I-, and CH3COO-. The color change of HNPTU upon treatment with CN- was maintained even in the presence of the comparable monovalent anions. The complex stability constant (Ka = 2.6 × 103) for the stoichiometric 1:1 complexation of HNPTU with cyanide ions was obtained based on absorbance titrations. The interaction of HNPTU with cyanide ions was proposed to be deprotonation, as shown by NMR and Cu(II) treatment experiments.

KW - Colorimetric sensor

KW - Cyanide ion

KW - Deprotonation

KW - Phenol

KW - Pyridyl

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U2 - 10.1016/j.tetlet.2014.09.049

DO - 10.1016/j.tetlet.2014.09.049

M3 - Article

AN - SCOPUS:84911884355

SN - 0040-4039

VL - 55

SP - 6965

EP - 6968

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Selective colorimetric assay of cyanide ions using a thioamide-based probe containing phenol and pyridyl groups

Abstract

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Keywords

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