European Journal of Chemistry

Selective colorimetric molecular probe for cyanide ion detection in aqueous solution

Article Sidebar

PDF
Published: Dec 31, 2018
DOI: https://doi.org/10.5155/eurjchem.9.4.338-346.1777
Keywords:
DFT, Cyanide, Cyanohydrin, UV-vis spectroscopy, Visual molecular probe, 5-Nitro-2-hydroxybenzaldehyde
Section
Research Article
Issue
Vol. 9 No. 4 (2018): December 2018
Dates
Received 2018-07-28
Accepted 2018-09-12
Published 2018-12-31
Crossmark


Main Article Content

Yousef Mohammad Hijji
Department of Chemistry and Earth Sciences, Qatar University, Doha, 2713, Qatar
http://orcid.org/0000-0002-4116-1746
Hani Darwish Tabba
Department of Chemistry and Earth Sciences, Qatar University, Doha, 2713, Qatar
http://orcid.org/0000-0002-5313-6951
Rajeesha Rajan
Department of Chemistry and Earth Sciences, Qatar University, Doha, 2713, Qatar
http://orcid.org/0000-0002-8798-8992
Hamzeh Mohammad Abdel-Halim
Department of Chemistry, The Hashemite University, Zarqa 13133, Jordan
http://orcid.org/0000-0003-0564-7922
Musa Ibrahim El-Barghouthi
Department of Chemistry, The Hashemite University, Zarqa 13133, Jordan
http://orcid.org/0000-0003-1961-796X
Hutaf Mustafa Baker
Department of Chemistry, Al Al-Bayt University, Mafraq 25113, Jordan
http://orcid.org/0000-0002-0690-0726

Abstract

5-Nitro-2-hydroxybenzaldehyde (1) demonstrated to be a sensitive, and a selective molecular probe for cyanide ion (CN-) in aqueous media. In acetonitrile, compound 1 shows sensitivity and selectivity for cyanide, acetate and fluoride, in comparison to other investigated anions using both visual and spectroscopic means. In aqueous solution, the color becomes intense yellow upon addition of cyanide, while acetate showed this effect to a much lower extent. Significant spectral changes were also detected with the appearance of two new absorption bands at 358 and 387 nm. This was accompanied by concomitant intensity decrease for the band at 314 nm. Fluoride, dihydrogen phosphate, chloride, bromide, perchlorate, and azide showed negligible color and spectral changes for the probe in aqueous solutions. On the other hand, hydrogen sulfate caused fainting of the yellow color and gave a spectrum similar to that of the sensor in polar aprotic solvents. The cyanide ion was detected at micro molar levels in aqueous solutions with a stoichiometry of 1:1 for CN: probe in acetonitrile as the solvent. Cyanide, hydroxide, acetate, fluoride and dihydrogen phosphate showed identical changes to color and spectra, indicating a hydrogen bonding and a deprotonation mechanism.


icon graph This Abstract was viewed 2388 times | icon graph Article PDF downloaded 729 times

How to Cite
(1)
Hijji, Y. M.; Tabba, H. D.; Rajan, R.; Abdel-Halim, H. M.; El-Barghouthi, M. I.; Baker, H. M. Selective Colorimetric Molecular Probe for Cyanide Ion Detection in Aqueous Solution. Eur. J. Chem. 2018, 9, 338-346.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Gotor, R.; Costero, A. M.; Gil, S.; Parra, M.; Martinez-Manez, R.; Sancenon, F. Chem. A Eur. J. 2011, 17, 11994-11997.
https://doi.org/10.1002/chem.201102241

[2]. Sun, W.; Guo, S.; Hu, C.; Fan, J.; Peng, X. Chem. Rev. 2016, 116, 7768-7817.
https://doi.org/10.1021/acs.chemrev.6b00001

[3]. Moragues, M. E.; Martinez-Manez, R.; Sancenon, F. Chem. Soc. Rev. 2011, 40, 2593-2643.
https://doi.org/10.1039/c0cs00015a

[4]. Zang, L.; Wei, D.; Wang, S.; Jiang, S. Tetrahedron 2012, 68, 636-641.
https://doi.org/10.1016/j.tet.2011.10.105

[5]. Sun, Y.; Wang, G.; Guo, W. Tetrahedron 2009, 65, 3480-3485.
https://doi.org/10.1016/j.tet.2009.02.023

[6]. Duke, R. M.; Veale, E. B.; Pfeffer, F. M.; Kruger, P. E.; Gunnlaugsson, T. Chem. Soc. Rev. 2010, 39, 3936-3953.
https://doi.org/10.1039/b910560n

[7]. Garcia, J. M.; Garcia, F. C.; Serna, F.; De La Pena, J. L. Polymer Rev. 2011, 51, 341-390.
https://doi.org/10.1080/15583724.2011.616084

[8]. Gunnlaugsson, T.; Glynn, M.; Tocci, G. M.; Kruger, P. E.; Pfeffer, F. M. Coord. Chem. Rev. 2006, 250, 3094-3117.
https://doi.org/10.1016/j.ccr.2006.08.017

[9]. Chang, K. C.; Sun, S. S.; Odago, M. O.; Lees, A. J. Coord. Chem. Rev. 2015, 284, 111-123.
https://doi.org/10.1016/j.ccr.2014.09.009

[10]. Wu, J.; Kwon, B.; Liu, W.; Anslyn, E. V.; Wang, P.; Kim, J. S. Chem. Rev. 2015, 115(15) 7893-7943.
https://doi.org/10.1021/cr500553d

[11]. Udhayakumari, D. Sensors Actuators B: Chem. 2018, 259, 1022-1057.
https://doi.org/10.1016/j.snb.2017.12.006

[12]. Bhattacharya, R.; Flora, S. J. S. In Handbook of Toxicology of Chemical Warfare Agents (Second Edition); Gupta, R. C., Ed.; Academic Press: Boston, 2015, 301-314.
https://doi.org/10.1016/B978-0-12-800159-2.00023-3

[13]. Gilley, C.; MacDonald, M.; Nachon, F.; Schopfer, L. M.; Zhang, J.; Cashman, J. R.; Lockridge, O. Chem. Res. Toxicol. 2009, 22, 1680-1688.
https://doi.org/10.1021/tx900090m

[14]. Rhee, J.; Jung, J.; Yeom, H.; Lee, H.; Lee, S.; Park, Y.; Chung, H. Forensic Sci. Inter. 2011, 210, e12-e15.
https://doi.org/10.1016/j.forsciint.2011.04.014

[15]. Xu, Z.; Chen, X.; Kim, H. N.; Yoon, J. Chem. Soc. Rev. 2010, 39, 127-137.
https://doi.org/10.1039/B907368J

[16]. Hijji, Y. M.; Barare, B.; Kennedy, A. P.; Butcher, R. Sensors Actuators B: Chem. 2009, 136, 297-302.
https://doi.org/10.1016/j.snb.2008.11.045

[17]. Odago, M. O.; Colabello, D. M.; Lees, A. J. Tetrahedron 2010, 66, 7465-7471.
https://doi.org/10.1016/j.tet.2010.07.006

[18]. Jo, H. Y.; Lee, S. A.; Na, Y. J.; Park, G. J.; Kim, C. Inorg. Chem. Commun. 2015, 54, 73-76.
https://doi.org/10.1016/j.inoche.2015.02.014

[19]. Elsafy, A.; Al-Easa, H.; Hijji, Y. Sensors 2018, 18, 2219-2230.
https://doi.org/10.3390/s18072219

[20]. Wei, T.; Li, H.; Wang, Q.; Yan, G.; Zhu, Y.; Lu, T.; Shi, B.; Lin, Q.; Zhang, Y. Supramol. Chem. 2016, 28, 314-320.
https://doi.org/10.1080/10610278.2015.1108419

[21]. Lee, E. M.; Gwon, S. Y.; Son, Y. A.; Kim, S. H. Spectrochim. Acta A 2012, 95, 25-28.
https://doi.org/10.1016/j.saa.2012.04.080

[22]. Yu, Y.; Shu, T.; Yu, B.; Deng, Y.; Fu, C.; Gao, Y.; Dong, C.; Ruan, Y. Sensors Actuators B: Chem. 2018, 255, 3170-3178.
https://doi.org/10.1016/j.snb.2017.09.142

[23]. Zhou, C.; Sun, M.; Yan, C.; Yang, Q.; Li, Y.; Song, Y. Sensors Actuators B: Chem. 2014, 203, 382-387.
https://doi.org/10.1016/j.snb.2014.07.002

[24]. Lou, X.; Ou, D.; Li, Q.; Li, Z. Chem. Commun. 2012, 48, 8462-8477.
https://doi.org/10.1039/c2cc33158f

[25]. Tang, Y. H.; Qu, Y.; Song, Z.; He, X. P.; Xie, J.; Hua, J.; Chen, G. R. Org. Biomol. Chem. 2012, 10, 555-560.
https://doi.org/10.1039/C1OB06242E

[26]. Jung, H. S.; Han, J. H.; Kim, Z. H.; Kang, C.; Kim, J. S. Org. Lett. 2011, 13, 5056-5059.
https://doi.org/10.1021/ol2018856

[27]. Chen, H.; Liu, Z.; Cao, D.; Lu, S.; Pang, J.; Sun, Y. Sensors Actuators B: Chem. 2014, 199, 115-120.
https://doi.org/10.1016/j.snb.2014.03.106

[28]. Isaad, J.; El Achari, A. Tetrahedron 2011, 67, 4939-4947.
https://doi.org/10.1016/j.tet.2011.04.061

[29]. Lee, J. H.; Jeong, A. R.; Shin, I. S.; Kim, H. J.; Hong, J. I. Org. Lett. 2010, 12, 764-767.
https://doi.org/10.1021/ol902852g

[30]. Dong, X.; Zhou, Y.; Song, Y.; Qu, J. J. Fluor. Chem. 2015, 178, 61-67.
https://doi.org/10.1016/j.jfluchem.2015.06.025

[31]. Dong, Y. M.; Peng, Y.; Dong, M.; Wang, Y. W. J. Org. Chem. 2011, 76, 6962-6966.
https://doi.org/10.1021/jo201269e

[32]. Lin, Y. D.; Peng, Y. S.; Su, W.; Tu, C. H.; Sun, C. H.; Chow, T. J. Tetrahedron 2012, 68, 2523-2526.
https://doi.org/10.1016/j.tet.2012.01.026

[33]. Park, S.; Kim, H. J. Sensors Actuators B: Chem. 2012, 161, 317-321.
https://doi.org/10.1016/j.snb.2011.10.038

[34]. Fu, G. L.; Zhao, C. H. Tetrahedron 2013, 69, 1700-1704.
https://doi.org/10.1016/j.tet.2012.12.034

[35]. Niamnont, N.; Khumsri, A.; Promchat, A.; Tumcharern, G.; Sukwattanasinitt, M. J. Hazard. Mater. 2014, 280, 458-463.
https://doi.org/10.1016/j.jhazmat.2014.08.028

[36]. Bejoymohandas, K. S.; Kumar, A.; Sreenadh, S.; Varathan, E.; Varughese, S.; Subramanian, V.; Reddy, M. L. P. Inorg. Chem. 2016, 55, 3448-3461.
https://doi.org/10.1021/acs.inorgchem.5b02885

[37]. Huo, F.; Zhang, Y.; Yue, Y.; Chao, J.; Zhang, Y.; Yin, C. Dyes Pigments 2017, 143, 270-275.
https://doi.org/10.1016/j.dyepig.2017.04.050

[38]. Kim, D. S.; Chung, Y. M.; Jun, M.; Ahn, K. H. J. Org. Chem. 2009, 74, 4849-4854.
https://doi.org/10.1021/jo900573v

[39]. Isaad, J.; Perwuelz, A. Tetrahedron Lett. 2010, 51, 5810-5814.
https://doi.org/10.1016/j.tetlet.2010.08.098

[40]. Ding, Y.; Li, T.; Zhu, W.; Xie, Y. Org. Biomol. Chem. 2012, 10, 4201-4207.
https://doi.org/10.1039/c2ob25297j

[41]. Isaad, J.; Achari, A. E. Anal. Chim. Acta 2011, 694, 120-127.
https://doi.org/10.1016/j.aca.2011.03.032

[42]. Isaad, J.; El Achari, A. Tetrahedron 2011, 67, 4196-4201.
https://doi.org/10.1016/j.tet.2011.04.059

[43]. Goswami, S.; Manna, A.; Paul, S.; Aich, K.; Das, A. K.; Chakraborty, S. Tetrahedron Lett. 2013, 54, 1785-1789.
https://doi.org/10.1016/j.tetlet.2012.12.092

[44]. Saravanakumar, D.; Devaraj, S.; Iyyampillai, S.; Mohandoss, K.; Kandaswamy, M. Tetrahedron Lett. 2008, 49, 127-132.
https://doi.org/10.1016/j.tetlet.2007.11.006

[45]. Hijji, Y. M.; Barare, B.; Zhang, Y. Sensors Actuators, B: Chem. 2012, 169, 106-112.
https://doi.org/10.1016/j.snb.2012.03.067

[46]. Kumar, S.; Singh, P.; Hundal, G.; Singh Hundal, M. Chem. Commun. 2013, 49, 2667-2669.
https://doi.org/10.1039/c3cc40435h

[47]. Lin, Y. S.; Zheng, J. X.; Tsui, Y. K.; Yen, Y. P. Spectrochim. Acta A 2011, 79, 1552-1558.
https://doi.org/10.1016/j.saa.2011.04.087

[48]. Kang, J.; Song, E. J.; Kim, H.; Kim, Y. H.; Kim, Y.; Kim, S. J.; Kim, C. Tetrahedron Lett. 2013, 54, 1015-1019.
https://doi.org/10.1016/j.tetlet.2012.12.053

[49]. Niu, H. T.; Su, D.; Jiang, X.; Yang, W.; Yin, Z.; He, J.; Cheng, J. P. Org. Biomol. Chem. 2008, 6, 3038-3040.
https://doi.org/10.1039/b808589g

[50]. Jang, H. J.; Kang, J. H.; Lee, M.; Lim, M. H.; Kim, C. Ind. Eng. Chem. Res. 2018, 57, 54-62.
https://doi.org/10.1021/acs.iecr.7b03826

[51]. Li, H.; Li, B.; Jin, L. Y.; Kan, Y.; Yin, B. Tetrahedron 2011, 67, 7348-7353.
https://doi.org/10.1016/j.tet.2011.07.023

[52]. Yang, Y. K.; Tae, J. Organic Lett. 2006, 8, 5721-5723.
https://doi.org/10.1021/ol062323r

[53]. Guo, Y. Y.; Tang, X. L.; Hou, F. P.; Wu, J.; Dou, W.; Qin, W. W.; Ru, J. X.; Zhang, G. L.; Liu, W. S.; Yao, X. J. Sensors Actuators B: Chem. 2013, 181, 202-208.
https://doi.org/10.1016/j.snb.2013.01.053

[54]. Gaussian 03. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.;. Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T. Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh PA, 2003.

[55]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
https://doi.org/10.1063/1.464913

[56]. Lee, C.; Yang, W.; Parr, R. G. Physical Rev. B 1988, 37, 785-789.
https://doi.org/10.1103/PhysRevB.37.785

[57]. Runge, E.; Gross, E. K. U. Phys. Rev. Lett. 1984, 52, 997-1000.
https://doi.org/10.1103/PhysRevLett.52.997

[58]. Casida, M. K.; Chong, D. P., Ed.; Recent advances in density and functional methods, World Scientific, Singapore 1995; Vol. 1, pp. 155-192.
https://doi.org/10.1142/9789812830586_0005

[59]. O'Boyle, N. M.; Tenderholt, A. L.; Langner, K. M. J. Comp. Chem. 2008, 29, 839-645.
https://doi.org/10.1002/jcc.20823

[60]. Jana, S.; Dalapati, S.; Alam, M. A.; Guchhait, N. Spectrochim. Acta A 2012, 92, 131-136.
https://doi.org/10.1016/j.saa.2012.02.028

[61]. Pati, P. B.; Zade, S. S. Eur. J. Org. Chem. 2012, 2012, 6555-6561.

Supporting Agencies

National Priority Research Program (NPRP) award [NPRP-7-495-01-094] from the Qatar National Research Fund (a member of The Qatar Foundation), Qatar
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).