RESEARCH PAPERSNo Access

Quantum chemical insight into the molecular structure of L-chemosensor 1,3-dimethyl-5-(thien-2-ylmethylene)-pyrimidine-2,4,6-(1H,3H,5H)-trione: Naked-eye colorimetric detection of copper(II) anions

Assem Barakat

Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia

Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt

E-mail Address: ambarakat@ksu.edu.sa

Corresponding authors.

Search for more papers by this author

Mohammad Shahidul Islam

Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia

Search for more papers by this author

Abdullah Mohammed Al-Majid

Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia

Search for more papers by this author

Hazem A. Ghabbour

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia

Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt

Search for more papers by this author

Saleh Atef

Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia

Search for more papers by this author

Abdelkader Zarrouk

LCAE-URAC18, Faculté des Sciences d’Oujda, Université Mohammed Premier, BP 4808, 60046 Oujda, Morocco

Search for more papers by this author

, and

Ismail Warad

Department of Chemistry, Science College, An-Najah National University, P. O. Box 7, Nablus, Palestine

E-mail Address: warad@najah.edu

Corresponding authors.

Search for more papers by this author

https://doi.org/10.1142/S0219633618500050Cited by:11 (Source: Crossref)

Abstract

A sensitive colorimetric L-chemosensor 1,3-dimethyl-5-(thien-2-ylmethylene)-pyrimidine-2,4,6-(1 $H, 3 H, 5 H)$ -trione was developed by Knoevenagel combination of barbituric acid with thiophene aldehyde chelating moiety. The sensor displayed a high colorimetric Cu(II)X₂ response; a dramatic methanol color change was recorded depending on anion type ( $X = {Br}^{- 1}$ , Cl $^{- 1}$ , ClO $_{4}^{- 1}$ , NO $_{3}^{- 1}$ , OAc $^{- 1}$ , and SO $_{4}^{- 2})$ . Off-on-off decolorized halochromism of the L-chemosensor/CuBr₂ was recorded in an acidic medium. The structure of the L-chemosensor was confirmed by single-crystal X-ray diffraction, elemental analysis, and molecular spectroscopic tools such as UV–Vis, Fourier transform infra-red, ¹H, and $^{13}$ C nuclear magnetic resonance (NMR) spectroscopy. The thermal stability of the L-chemosensor was experimentally evaluated by thermogravimetric analysis. The structural optimized parameters of the ligand matched the crystallographic data, and the intermolecular forces were computed by Hirshfeld surface analysis. Electronic absorption in several solvents and ¹H NMR were correlated with the computed spectra in the gaseous state. The HOMO/LUMO, global reactivity descriptor quantum parameters, Mulliken charge population, and molecular electrostatic potential of the L-chemosensor were also computed.

Keywords:

References

1. Barakat A, Soliman SM, Ghabbour HA, Ali M, Al-Majid AM, Zarrouk A, Warad I, Intermolecular interactions in crystal structure, Hirshfeld surface, characterization, DFT and thermal analysis of 5-((5-bromo-1 $H$ -indol-3-yl)methylene)-1,3-dimethylpyrimidine-2,4,6- (1 $H$ ,3 $H$ ,5 $H)$ -trione indole, J Mol Struct 1137 :354–361, 2017. Crossref, Web of Science, Google Scholar
2. Ziarani GM, Aleali F, Lashgari N, Recent applications of barbituric acid in multicomponent reactions, RSC Adv 6 :50895–50922, 2016. Crossref, Web of Science, Google Scholar
3. Pagé D, Yang H, Brown W, Walpole C, Fleurent M, Fyfe M, Gaudreault F, St-Onge S, New 1,2,3,4-tetrahydropyrrolo [3, 4- $b$ ] indole derivatives as selective CB2 receptor agonists, Bioorg Med Chem Lett 17 :6183–6187, 2007. Crossref, Web of Science, Google Scholar
4. Radwan MA, Ragab EA, Sabry NM, El-Shenawy SM, Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents, Bioorg Med Chem 15 :3832–3841, 2007. Crossref, Web of Science, Google Scholar
5. Golchoubian H, Moayyedi G, Reisi N, Halochromism, ionochromism, solvatochromism and density functional study of a synthesized copper(II) complex containing hemilabile amide derivative ligand, Spectrochimica Acta A 138 :913–924, 2015. Crossref, Web of Science, Google Scholar
6. Patra GK, Chandra R, Ghorai A, Shrivas KK, A highly selective benzildihydrazone based Schiff base chromogenic chemosensor for rapid detection of Cu $^{2+}$ in aqueous solution, Inorg Chim Acta 462 :315–322, 2017. Crossref, Web of Science, Google Scholar
7. Meinershagen JL, Bein T, Solvatochromism of a copper (ii)(tetramethylethylenediamine) − (acetylacetonate) $+$ complex encapsulated in EMT zeolite cages. Adv Mater 13 (3): 208–211, 2001. Crossref, Web of Science, Google Scholar
8. Gou M, Guo G, Zhang J, Men K, Song J, Luo F, Zhi XZ, Qian Y, Wei, Y, Time–temperature chromatic sensor based on polydiacetylene (PDA) vesicle and amphiphilic copolymer. Sens Actuat B: Chem 150 :406–411, 2010. Crossref, Web of Science, Google Scholar
9. Fegadea U, Sahoo SK, Attarde S, Singh N, Kuwar A, Colorimetric and fluorescent “on–off” chemosensor for Cu $^{2+}$ in semi-aqueous medium, Sensor Actuat B-Chem 202 :924–928, 2014. Crossref, Web of Science, Google Scholar
10. Barakat A, Islam MS, Al-Majid AM, Ghabbour HA, Yousuf S, Ashraf M, Shaikh NN, Choudhary MI, Khalil R, Ul-Haq Z, Synthesis of pyrimidine-2,4,6-trione derivatives: Anti-oxidant, anti-cancer, $α$ -glucosidase, $β$ -glucuronidase inhibition and their molecular docking studies, Bioorg Chem 68 :72–79, 2016. Crossref, Web of Science, Google Scholar
11. Biradar JS, Sasidhar BS, Parveen R, Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives, Eur J Med Chem 45 :4074–4078, 2010. Crossref, Web of Science, Google Scholar
12. Ye D, Zhang Y, Wang F, Zheng M, Zhang X, Luo X, Shen X, Jiang H, Liu H, Novel thiophene derivatives as PTP1B inhibitors with selectivity and cellular activity, Bioorg Med Chem 18 :1773–1782, 2010. Crossref, Web of Science, Google Scholar
13. Saad HA, Youssef MM, Mosselhi MA, Microwave assisted synthesis of some new fused 1,2,4-triazines bearing thiophene moieties with expected pharmacological activity, Molecules 16 :4937–4957, 2011. Crossref, Web of Science, Google Scholar
14. Kulandasamy R, Adhikari AV, Stables JP, A new class of anticonvulsants possessing 6Hz activity: 3,4-dialkyloxy thiophene bishydrazones, Eur J Med Chem 44 :4376–4384, 2009. Crossref, Web of Science, Google Scholar
15. Frisch M, Trucks GW, Schlegel H, Scuseria GE, Robb MA, Cheeseman JR, Millam JM, Gaussian 03, Revision c. 02, Gaussian Inc., Wallingford, CT, 4, 2004. Google Scholar
16. Ennington R, Keith T, Millam J, Semichem Inc., Shawnee Mission KS, GaussView, Version, 5, 2009. Google Scholar
17. Wolff SK, Grimwood DJ, McKinnon JJ, Jayatilaka D, Spackman MA, Crystal Explorer 2.1. University of Western Australia, Perth, 2007. Google Scholar
18. Sheldrick GM, A short history of SHELX, Acta Cryst 64 :112–122, 2008. Crossref, Web of Science, Google Scholar
19. Spek AL, Structure validation in chemical crystallography, Acta Cryst 65 :148–155, 2009. Crossref, Web of Science, Google Scholar
20. Spackman MA, Jayatilaka D, Hirshfeld surface analysis, CrystEngComm 11 :19–32, 2009. Crossref, Web of Science, Google Scholar
21. Spackman MA, McKinnon JJ, Fingerprinting intermolecular interactions in molecular crystals, CrystEngComm 4 :378–392, 2002. Crossref, Web of Science, Google Scholar
22. Warad I, Barakat A, Synthesis, physicochemical analysis of two new hemilabile ether-phosphine ligands and their first stable bis-ether-phosphine/cobalt(II) tetrahedral complexes, J Mol Struct 1134 :17–24, 2017. Crossref, Web of Science, Google Scholar
23. Saleemh FA, Musameh S, Sawafta A, Brandao P, Tavares CJ, Ferdov S, Barakat A, Al Ali A, Al-Noaimi M, Warad I, Diethylenetriamine/diamines/copper (II) complexes [Cu(dien)(NN)]Br2: Synthesis, solvatochromism, thermal, electrochemistry, single crystal, Hirshfeld surface analysis and antibacterial activity, Arab J Chem 10 :845–854, 2017. Crossref, Web of Science, Google Scholar
24. Banfi D, Patiny L, www.nmrdb.org: Resurrecting and processing NMR spectra on-line, Chimia 62 :280–281, 2008. Crossref, Web of Science, Google Scholar
25. Thirunarayanan S, Arjunan V, Marchewka MK, Mohan S, Atalay Y, Characterization of 1,3-diammonium propylselenate monohydrate by XRD, FT-IR, FT-Raman, DSC and DFT studies, J Mol Struct 1107 :220–230, 2016. Crossref, Web of Science, Google Scholar
26. Jasmine NJ, Arunagiri C, Stanley AS, Muthiah P, Synthesis, X-ray structure analysis, thermodynamic and electronic properties of 4-acetamido benzaldehyde using vibrational spectroscopy and DFT calculations, J Mol Struct 1130 :244–250, 2017. Crossref, Web of Science, Google Scholar
27. Asadi Z, Esrafili MD, Vessally E, Asnaashariisfahani M, Yahyaei S, Khani A, A structural study of fentanyl by DFT calculations, NMR and IR spectroscopy, J Mol Struct 1128 :552–562, 2017. Crossref, Web of Science, Google Scholar
28. Mulliken RS, Electronic population analysis on LCAO-MO molecular wave functions, J Chem Phys 23 :1833–1840, 1955. Crossref, Web of Science, Google Scholar