Journal of Multidisciplinary Applied Natural Science
an Open Access Journal
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2.1
Calculated on 05 May, 2025
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0.25
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an Open Access Journal
2.1
Calculated on 05 May, 2025
0.25
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https://doi.org/10.47352/jmans.2774-3047.460
Venty Suryanti
Laras Ayu Wijayanti
Yoga Royandana Firdaus
Fajar Rakhman Wibowo
Ahmad Marzuki
The compound N-(3-aminopropyl)-2-(4-allyl-2-methoxyphenoxy)acetamide (4) was synthesized from eugenol through a three-step reaction. Possessing both amide and amine groups, the molecule provides effective hydrogen-bond donor sites suitable for anion recognition. The binding behaviour of compound 4 toward F⁻, CN⁻, AcO⁻, SO₄²⁻, and H₂PO₄⁻ was examined using 1H-NMR spectroscopy. No significant spectral changes were observed upon addition of F⁻, AcO⁻, or SO₄²⁻, indicating minimal or no interaction. In contrast, the introduction of CN⁻ and H₂PO₄⁻ produced notable chemical shift variations, consistent with hydrogen-bond formation and host-guest complexation. To further elucidate these interactions, density functional theory (DFT) calculations were performed at the aug-cc-pVDZ level. Computational models revealed that F⁻ and AcO⁻ induce cleavage of the amide N–H bond through strong hydrogen bonding and partial covalent character, whereas CN⁻ and H₂PO₄⁻ primarily engage in hydrogen-bonding interactions without bond cleavage. Gauge-independent atomic orbital (GIAO) calculations predicted substantial downfield shifts of the amide proton, from 4.72 ppm in the free receptor to 15.5, 10.89, 16.54, and 12.27 ppm for F⁻, CN⁻, AcO⁻, and H₂PO₄⁻, respectively. Overall, both experimental and computational findings demonstrate that compound 4 functions as an effective receptor for CN⁻ and H₂PO₄⁻, with strong theoretical binding responses also observed for F⁻ and AcO⁻.
[1] L. Chen, S. N. Berry, X. Wu, E. N. W. Howe, and P. A. Gale. (2020). "Advances in Anion Receptor Chemistry". Chem. 6 (1): 61–141. 10.1016/j.chempr.2019.12.002.
DOI: https://doi.org/10.1016/j.chempr.2019.12.002[2] K. Maslowska-Jarzyna, E. York, E. Feo, R. M. Maklad, G. Bao, M. Fares, and P. A. Gale. (2025). "Recent Discoveries in Anion Receptor Chemistry". Chem. 11 (8): 102695. 10.1016/j.chempr.2025.102695.
DOI: https://doi.org/10.1016/j.chempr.2025.102695[3] H. Narkhede, A. Tupe, M. Kumbhare, A. Surana, and K. Khedkar. (2025). "Molecular Recognition for Anion Detection: Progress and Environmental Significance". Intelligent Pharmacy. 3 (6): 387–400. 10.1016/j.ipha.2025.07.001.
DOI: https://doi.org/10.1016/j.ipha.2025.07.001[4] T. S. Pandian, S. J. Cho, and J. Kang. (2013). "Dihydrogen Phosphate as a Hydrogen-Bonding Donor Element: Anion Receptors Based on Acylhydrazone". Journal of Organic Chemistry. 78 (23): 12121–12127. 10.1021/jo402103d.
DOI: https://doi.org/10.1021/jo402103d[5] A. Berkinbayeva, B. Kenzhaliyev, K. Smailov, A. Aimagambetov, B. Kamenov, S. Saulebekkyzy, N. Tolegenova, and P. S. R. Putri. (2025). "An Overview of Biological Cyanide Elimination from Tailing Wastewater as a Promising Tool for Sustainable Utilization". Water Research X. 29 : 100400. 10.1016/j.wroa.2025.100400.
DOI: https://doi.org/10.1016/j.wroa.2025.100400[6] K. Nagaraj, A. N. Shetty, and D. R. Trivedi. (2021). "Recent Advances in the Fluorescent and Colorimetric Detection of Dihydrogen Phosphate". Supramolecular Chemistry. 33 (8): 408–441. 10.1080/10610278.2022.2035387.
DOI: https://doi.org/10.1080/10610278.2022.2035387[7] B. Barare, I. Babahan, Y. M. Hijji, E. Bonyi, S. Tadesse, and K. Aslan. (2016). "A Highly Selective Sensor for Cyanide in Organic Media and on Solid Surfaces". Sensors. 16 (3): 271. 10.3390/s16030271.
DOI: https://doi.org/10.3390/s16030271[8] S. Ramesh and S. Kumaresan. (2021). "A Highly Selective Coumarin-Based Chemosensor for Naked-Eye Detection of Cyanide Anions via Nucleophilic Addition in Pure Aqueous Environment". Microchemical Journal. 169 : 106584. 10.1016/j.microc.2021.106584.
DOI: https://doi.org/10.1016/j.microc.2021.106584[9] V. Suryanti, H. A. Setyono, Y. Hidayat, D. S. Black, and N. Kumar. (2025). "Synthesis, Spectroscopic Studies and Computational Modelling of Anthracene-bis-N-Acetylglyoxylic Amide Derivative for Anion Recognition". RSC Advances. 15 : 27772–27781. 10.1039/D5RA03382A.
DOI: https://doi.org/10.1039/D5RA03382A[10] A. A. Veettil and S. M. Basheer. (2025). "Novel Colorimetric Anthracene-Based Thiosemicarbazone Probe for Selective Cyanide Ion Detection: From Synthesis to Real-Time Applications". ACS Omega. 10 (44): 52730–52744. 10.1021/acsomega.5c06461.
DOI: https://doi.org/10.1021/acsomega.5c06461[11] V. Suryanti, M. Bhadbhade, H. M. Chawla, E. Howe, P. Thordarson, D. S. Black, and N. Kumar. (2014). "Novel Colorimetric Anion Sensors Based on N-Acetylglyoxylic Amides Containing Nitrophenyl Signaling Units". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 121 : 662–669. 10.1016/j.saa.2013.11.108.
DOI: https://doi.org/10.1016/j.saa.2013.11.108[12] V. Suryanti, M. Bhadbhade, D. S. Black, and N. Kumar. (2017). "N-Acetylglyoxylic Amide Bearing a Nitrophenyl Group as Anion Receptors: NMR and X-Ray Investigations on Anion Binding and Selectivity". Journal of Molecular Structure. 1146 : 571–576. 10.1016/j.molstruc.2017.05.133.
DOI: https://doi.org/10.1016/j.molstruc.2017.05.133[13] P. D. Beer and P. A. Gale. (2001). "Anion Recognition and Sensing: The State of the Art and Future Perspectives". Angewandte Chemie International Edition. 40 (3): 486–516. 10.1002/1521-3773(20010202)40:3.
DOI: https://doi.org/10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P[14] J. Gomez-Vega, A. Vasquez-Cornejo, O. Juárez-Sánchez, D. O. Corona-Martínez, A. Ochoa-Terán, K. A. López-Gastelum, R. R. Sotelo-Mundo, H. Santacruz-Ortega, J. C. Gálvez-Ruiz, R. Pérez-González, and K. O. Lara. (2024). "Thiourea-Based Receptors for Anion Recognition and Signaling". ACS Omega. 9 (4): 4412–4422. 10.1021/acsomega.3c06861.
DOI: https://doi.org/10.1021/acsomega.3c06861[15] N. Kaur, G. Kaur, U. A. Fegade, A. Singh, S. K. Sahoo, A. S. Kuwar, and N. Singh. (2017). "Anion Sensing with Chemosensors Having Multiple NH Recognition Units". TrAC Trends in Analytical Chemistry. 95 : 86–109. 10.1016/j.trac.2017.08.003.
DOI: https://doi.org/10.1016/j.trac.2017.08.003[16] F. A. Mohammed, T. Xiao, L. Wang, and R. B. P. Elmes. (2024). "Macrocyclic Receptors for Anion Recognition". Chemical Communications. 60 : 11812–11836. 10.1039/D4CC04521A.
DOI: https://doi.org/10.1039/D4CC04521A[17] D. Barišić, F. Lešić, M. T. Vlašić, K. Užarević, N. Bregović, and V. Tomišić. (2022). "Anion Binding by Receptors Containing NH Donating Groups: What Do Anions Prefer?". Tetrahedron. 120 : 132875. 10.1016/j.tet.2022.132875.
DOI: https://doi.org/10.1016/j.tet.2022.132875[18] I. Ravikumar, P. S. Lakshminarayanan, and P. Ghosh. (2010). "Anion Binding Studies of Tris(2-aminoethyl)amine Based Amide Receptors with Nitro Functionalized Aryl Substitutions: A Positional Isomeric Effect". Inorganica Chimica Acta. 363 (12): 2886–2895. 10.1016/j.ica.2010.02.030.
DOI: https://doi.org/10.1016/j.ica.2010.02.030[19] R. Biswas, S. Ghorai, B. Paul, S. Maji, and R. Natarajan. (2023). "Cleft Receptor for the Recognition and Extraction of Tetrahedral Oxyanions". Crystal Growth & Design. 23 (6): 4384–4394. 10.1021/acs.cgd.3c00167.
DOI: https://doi.org/10.1021/acs.cgd.3c00167[20] Q. Li, Y. Yue, Y. Guo, and S. Shao. (2012). "Fluoride Anions Triggered "OFF-ON" Fluorescent Sensor for Hydrogen Sulfate Anions Based on a BODIPY Scaffold That Works As a Molecular Keypad Lock". Sensors and Actuators B: Chemical. 173 : 797–801. 10.1016/j.snb.2012.07.105.
DOI: https://doi.org/10.1016/j.snb.2012.07.105[21] F. M. Pfeffer, A. M. Buschgens, N. W. Barnett, T. Gunnlaugsson, and P. E. Kruger. (2005). "4-Amino-1,8-Naphthalimide-Based Anion Receptors: Employing the Naphthalimide N-H Moiety in the Cooperative Binding of Dihydrogenphosphate". Tetrahedron Letters. 46 (38): 6579–6584. 10.1016/j.tetlet.2005.07.067.
DOI: https://doi.org/10.1016/j.tetlet.2005.07.067[22] J. R. A. Coelho, A. R. F. Pacheco, D. C. Domingues, A. R. O. Rodrigues, A. A. Temitope, P. J. G. Coutinho, M. J. G. Fernandes, E. M. S. Castanheira, and M. S. T. Gonçalves. (2025). "New Cation Sensors Based on Eugenol-Derived Azo Dyes". Molecules. 30 (13): 2788. 10.3390/molecules30132788.
DOI: https://doi.org/10.3390/molecules30132788[23] M. Khatun, A. Sanphui, S. Malik, S. G. Chowdhury, P. Karmakar, and A. Saha. (2025). "An Eugenol-Sulfonyl Based Fluorescent Probe for Recognition of Al3+ in Real Sample Analysis and Biological Application". Journal of Photochemistry and Photobiology A: Chemistry. 459 : 116023. 10.1016/j.jphotochem.2024.116023.
DOI: https://doi.org/10.1016/j.jphotochem.2024.116023[24] M. Khatun, J. Mandal, R. Ganguly, A. Barui, S. Banerjee, and A. Saha. (2025). "Derivative of Clove Oil Used as a Chemosensor for the Colorimetric and Fluorometric Detection of Al3+: Crystal Structure Description and Live Cell Imaging". New Journal of Chemistry. 49 : 3724–3735. 10.1039/D4NJ04724A.
DOI: https://doi.org/10.1039/D4NJ04724A[25] M. J. Priya, H. D. Revanasiddappa, B. Jayalakshmi, A. Swamynayaka, M. Madegowda, M. Iqbal, C. Shivamallu, K. S. Abass, R. G. Amachawadi, E. Silina, V. Stupin, and S. P. Kollur. (2025). "A Reversible Eugenol Derived Colorimetric and Fluorescence "Turn-Off" Probe for Fe2+ and Pb2+ Ions Detection". Scientific Reports. 15 (1): 31264. 10.1038/s41598-025-14725-2.
DOI: https://doi.org/10.1038/s41598-025-14725-2[26] V. Suryanti, F. R. Wibowo, and S. Handayani. (2020). "Methyl-3-(2-hydroxy-5-nitrophenyl amino)-3-phenylpropanoate Based Colorimetric Sensor for Oxyanions". Indonesian Journal of Chemistry. 20 (2): 257–263. 10.22146/ijc.39559.
DOI: https://doi.org/10.22146/ijc.39559[27] V. Suryanti, F. R. Wibowo, A. Marzuki, and M. R. K. Sari. (2020). "Cation Sensing Capabilities of a Nitrophenyl Cinnamaldehyde Derivative". Molekul. 15 (3): 191–198. 10.20884/1.jm.2020.15.3.654.
DOI: https://doi.org/10.20884/1.jm.2020.15.3.654[28] V. Suryanti, F. R. Wibowo, T. Kusumaningsih, A. H. Wibowo, S. A. Khumaidah, and L. A. Wijayanti. (2016). "Amidation Reaction of Eugenyl Oxyacetate Ethyl Ester with 1,3 Diaminopropane". 1725 : 020085. 10.1063/1.4945539.
DOI: https://doi.org/10.1063/1.4945539[29] H. Agarwalla, K. Jana, A. Maity, M. K. Kesharwani, B. Ganguly, and A. Das. (2014). "Hydrogen Bonding Interaction between Active Methylene Hydrogen Atoms and an Anion as a Binding Motif for Anion Recognition: Experimental Studies and Theoretical Rationalization". The Journal of Physical Chemistry A. 118 (14): 2656–2666. 10.1021/jp501769y.
DOI: https://doi.org/10.1021/jp501769y[30] X. F. Sun, Z. X. Zhang, W. Li, F. Q. Bai, J. Wang, R. Jia, C. P. Kong, and H. X. Zhang. (2016). "DFT/TD-DFT Calculations on the Sensing Mechanism of a Dual Response Near-Infrared Fluorescent Chemosensor for Superoxide Anion and Hydrogen Polysulfides: Photoinduced Electron Transfer". RSC Advances. 6 : 104735–104741. 10.1039/C6RA23724J.
DOI: https://doi.org/10.1039/C6RA23724J[31] G. M. Gholam, M. A. Dwicesaria, I. M. Artika, V. D. Kharisma, A. A. A. Murtadlo, S. Sahadewa, F. D. Durry, A. A. Parikesit, H. Purnobasuki, E. Volnova, Y. Lysenko, M. Rebezov, D. D. R. Turista, A. N. M. Ansori, and T. H. Sucipto. (2025). "Indonesian Herbal Compounds as Potential Inhibitors of Plasmodium falciparum CDPK2: Insights from Docking, Molecular Dynamics, and DFT Analysis". Journal of Pharmacy and Pharmacognosy Research. 13 (Supplement 1): S289–S302. 10.56499/jppres25.2336_13.s1.289.
DOI: https://doi.org/10.56499/jppres25.2336_13.s1.289[32] M. F. Maahury, M. R. Sohilait, M. A. Martoprawiro, V. D. Kharisma, P. Listiyani, A. N. M. Ansori, S. L. Utami, A. P. Nugraha, I. Rosadi, R. S. Mandeli, M. A. Ghiffari, M. T. Albari, M. R. Ghiffari, and R. Zainul. (2023). "DFT and Molecular Docking Investigations of Curcuminoid on Tribolium castaneum Telomerase Enzyme". Research Journal of Pharmacy and Technology. 16 (10): 4817–4824. 10.52711/0974-360X.2023.00781.
DOI: https://doi.org/10.52711/0974-360X.2023.00781[33] G. M. Gholam, R. A. P. Irsal, F. R. Mahendra, M. A. Dwicesaria, J. E. Siregar, A. N. M. Ansori, and R. Zainul. (2024). "In Silico Computational Prediction of Saussurea pulchella Compounds with Inhibitory Effects on Plasmepsin X in Plasmodium falciparum". Informatics in Medicine Unlocked. 49 : 101549. 10.1016/j.imu.2024.101549.
DOI: https://doi.org/10.1016/j.imu.2024.101549[34] M. A. Hossain, P. Dewan, S. M. Kawsar, A. Dangwal, K. Kalra, J. M. Kalra, P. K. Ashok, T. Parashar, V. Jakhmola, S. Saha, and A. N. M. Ansori. (2025). "Chemical Descriptors, ADMET, Molecular Docking, and Molecular Dynamics Simulation of Mannopyranoside Derivatives Against Smallpox Virus Proteins". Advanced Journal of Chemistry, Section A. 8 (1): 1–16. 10.48309/ajca.2025.459071.1531.
[35] S. Kundu, T. K. Egboluche, and M. A. Hossain. (2023). "Urea- and Thiourea-Based Receptors for Anion Binding". Accounts of Chemical Research. 56 (11): 1320–1329. 10.1021/acs.accounts.2c00701.
DOI: https://doi.org/10.1021/acs.accounts.2c00701[36] Y. W. Liu, M. X. Kao, and A. T. Wu. (2015). "Discriminating Detection Between F− and CN− by Naked Eye from Schiff Base Sensor". Sensors and Actuators B: Chemical. 208 429–435. 10.1016/j.snb.2014.11.039.
DOI: https://doi.org/10.1016/j.snb.2014.11.039[37] M. O. Odago, D. M. Colabello, and A. J. Lees. (2010). "A Simple Thiourea-Based Colorimetric Sensor for Cyanide Anion". Tetrahedron. 66 (38): 7465–7471. 10.1016/j.tet.2010.07.006.
DOI: https://doi.org/10.1016/j.tet.2010.07.006[38] S. Goswami, S. Maity, A. K. Das, A. C. Maity, T. K. Mandal, and S. Samanta. (2013). "Remarkable ESIPT-Induced NIR Emission by a Selective Colorimetric Dibenzimidazolo Diimine Sensor for Acetate". Tetrahedron Letters. 54 (38): 5232–5235. 10.1016/j.tetlet.2013.07.078.
DOI: https://doi.org/10.1016/j.tetlet.2013.07.078[39] W. Huang, H. Su, J. Li, H. Lin, and H. Lin. (2010). "An Acetate Sensor Based on Azo in Aqueous Media". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 77 (1): 146–149. 10.1016/j.saa.2010.04.042.
DOI: https://doi.org/10.1016/j.saa.2010.04.042[40] J. Shao, H. Lin, and H. K. Lin. (2008). "A Simple and Efficient Colorimetric Anion Receptor for H2PO4". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 70 (3): 682–685. 10.1016/j.saa.2007.08.018.
DOI: https://doi.org/10.1016/j.saa.2007.08.018[41] N. J. Na, G. Jin-Park, H. Y. Jo, S. A. Lee, and C. Kim. (2014). "A Colorimetric Chemosensor Based on a Schiff Base for Highly Selective Sensing of Cyanide in Aqueous Solution: The Influence of Solvents". New Journal of Chemistry. 38 (12): 5769–5776. 10.1039/C4NJ01199F.
DOI: https://doi.org/10.1039/C4NJ01199F