Studi Teoritis Senyawa Turunan Kalkon Hidroksi Sebagai Sensor Kimia Berbagai Anion
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Studi secara teoritis telah dilakukan untuk mempelajari interaksi senyawa turunan kalkon hidroksi (CH) sebagai sensor kimia dengan anion F-, Cl-, Br-, CN-, CH3COO-, dan NO3-. Penelitian ini bertujuan untuk memodelkan struktur molekul senyawa turunan kalkon hidroksi (CH) dan sifat sensornya serta model interaksinya dengan anion dengan metode DFT. Hasil optimasi geometri menunjukkan terjadinya pemanjangan ikatan O-H sebesar 0,63-0,85 í… dengan adanya anion F-, CN-, and CH3COO-. Hal ini mengindikasikan terjadinya deprotonasi sensor kalkon hidroksi (CH) oleh anion. Sedangkan interaksi sensor kalkon hidroksi (CH) dengan anion Cl-, Br-, dan NO3- hanya berupa ikatan hidrogen dengan pemanjangan ikatan O-H sebesar 0,08-0,46 í…. Sensor kalkon hidroksi (CH) yang mengalami deprotonasi memiliki energi interaksi yang lebih besar yaitu -209,37 – -424,06 kJ/mol dibandingkan sensor yang hanya membentuk ikatan hidrogen yaitu -98,60 – -125,59 kJ/mol. Sensor yang mengalami deprotonasi mengakibatkan turunnya selisih energi HOMO-LUMO dari -3,94 – -4,06 eV menjadi -2,62 – -2,75 eV.
Kata kunci: sensor kimia, kalkon hidroksi, anion, DFT
Abstract
Theoretical study had been carried out to investigate interaction between hydroxy chalcone derivatives (CH) as chemosensors with F-, Cl-, Br-, CN-, CH3COO-, and NO3- anions. This study was aimed to design molecular structures of chemosensor hydroxy chalcone (CH) properties for the anions and their interaction models with DFT method. The result of geometry optimization showed 0,63-0,85 í… O-H bond elongation of the hydroxy chalcone was occured by F-, CN-, and CH3COO-. It was indicated deprotonation of sensor hydroxy chalcone (CH) by anions. Where as the interaction of the hydroxy chalcone (CH) with Cl-, Br-, and NO3- just formed an hydrogen bond with 0,08-0,46 í… O-H bond elongation. Deprotonized sensor hydroxy chalcone (CH) had more energy change of interaction -209,37– -424,06 kJ/mol than sensor which just formed the hydrogen bond -98,60 – -125,59 kJ/mol. Deprotonized sensor caused reduction of the difference of HOMO-LUMO energy from - 3,94 – -4,06 eV to -2,62 – -2,75 eV.
Keywords: chemosensor, hydroxy chalcone, anion, DFT
Cornard JP, and Lapouge C., 2006, Absorption Spectra of Caffeic Acid, Caffeate and Their 1:1 Complex with Al(III): Density Functional Theory and Time-Dependent Density Functional Theory Investigations, J. Phys. Chem. A., 110; 7159–7166.
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar S S, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas í–, Foresman JB, Ortiz JV, Cioslowski J, Fox D J., 2009, Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT.
Jin R, and Zhang J., 2009, Theoretical Investigation of Chemosensor for Fluoride Anion Based on Amidophthalimide Derivatives, Theor. Chem. Acc., 124(3); 225-234.
Jin R., 2011, Theoretical Study of Thiazole Derivatives as Chemosensors for Fluoride Anion, J. Fluor. Chem., 132; 907–914.
Jin R., 2012, Theoretical Study of Chemosensor for Fluoride Anion and Optical Properties of The Derivatives of Diketopyrrolopyrrole, Theor. Chem. Acc., 131; 1–10.
Li G, Zhao G, Han K, He G., 2010, A TD-DFT Study on The Cyanide- Chemosensing Mechanism of 8- Formyl-7-hydroxycoumarin, J. Comput Chem., 32(4); 668-674.
Reisi-Vanani A, and Alihoseini L., 2014, Computational Investigation of The Adsorption of Molecular Hydrogen on The Nitrogen-Doped Corannulene as A Carbon Nano-Structure, Surface Science., 621; 146-151.
Shan Y, Liu Z, Cao D, Liu G, Guan R, Sun N, Wang C, Wang K., 2015, Coumarinic Chalcone Derivatives as Chemosensors for Cyanide Anions and Copper Ions, Sens. Actuators B Chem., 221; 63-469.
Shan Y, Liu Z, Cao D, Sun Y, Wang K, Chen H., 2014, Nitro Substituted Chalcone Derivatives as Quick- Response Chemosensors for Cyanide Anions, Sensors and Actuators B: Chemical, 198; 15–19.
Steiner T, and Desiraju GR., 1998, Distinction Between The Weak Hydrogen Bond and The Van der Waals Interaction, Chem. Commun., 8; 891-892.
Steiner T., 2002, The Hydrogen Bond in The Solid State, Angew. Chem. Int. Ed., 41; 48-76.
Wang G, Xue Y, An L, Zheng Y, Dou Y, Zhang L, Liu Y., 2015, Theoretical Study on The Structural and Antioxidant Properties of Some Recently Synthesised 2,4,5- Trimethoxy Chalcones. Food Chem., 171; 89-97.
Zhang Y, Scanlon LG, Balbuena PB., 2007, Hydrogen Adsorption in Corannulene-Based Materials, Theo. Comput. Chem., 18; 127-166.
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