Araştırma Makalesi
Synthesis and Theoretical Analyses of Novel 5-mercapto-2-(5-methyl-furan-2-ylmethylidenamino)-1,3,4-thiadiazole Molecule
Öz
In this study, the novel 5 Mercapto 2--(5 methyl furan 2 yl 1,3,4 thiadiazole molecule was synthesized from the reaction of 2 amino 5 mercapto 1,3,4 thiadiazole with 5 methyl furan 2 carbaldehyde. The 5 Mercapto 2--(5 methyl furan 2 yl 1,3,4 thiadiazole was optimized by using DFT( HF methods. The mulliken charges, HOMO LUMO energy, ELUMO EHOMO energy gap (ΔEg), dipole moments, electron affinity (A), ionization potential (I), chemical softness (σ), chemical hardness (η), electronegativity (χ), bond angles, total energy and bond lengths of the molecule were calculated by using 6 31G(d,p) basis set with DFT (B3LYP) and HF methods. Otherwise, the 1H NMR and 13C NMR isotropic shift values were calculated by using GIAO methods with GaussianG09W package program. The experimental/theoretical values were compared and the regression analysis were found. Defining IR values were used the veda4f program. The theoretical infrared spectrums are visualised.
Anahtar Kelimeler
Kaynakça
- Dani RK, Bharty MK, Kushawaha SK, Prakash O, Singh RK, Singh NK, 2013. Hydration process as an activation of transand cisplatin complexes in anticancer treatment DFT and ab initio computational study of thermodynamic and kinetic parameters. Journal of Computational Chemistry, 26 (9): 907-914.
- Dennington R, Keith T, Millam J, 2009. GaussView, Version 5, Semichem Inc., Shawnee Mission KS.
- El-Gohary NS, Shaaban MI, 2013. Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles. European Journal of Medicinal Chemistry, 63: 185-195.
- Fukui K, Yonezawa T, Shingu HJ, 1952. A molecular orbital theory of reactivity in aromatic hydrocarbons. The Journal of Chemical Physics. 20: 722-725.
- Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X et al, 2009. Gaussian 09, Revision C.01, Gaussian, Inc. Wallingford, CT.
- Gür M, Muğlu H, Çavuş MS, Güder A, Sayıner HS, Kandemirli F, 2017. Synthesis, characterization, quantum chemical and evaluation of antioxidant properties of 1,3,4-thiadiazole derivatives including 2- and 3-methoxy cinnamic acids. Journal of Molecular Structure, 1134: 40-50. Jamróz MH, 2004. Vibrational Energy Distribution Analysis, VEDA 4 program, Warsaw.
- Kotan G, Özdemir G, Yüksek H, 2018. Investigation of Spectroscopic, Electronic and Geometric Properties of 2-(3-Methyl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethine)-benzoic acid Using B3lyp and Hf Basis Sets. Der Pharma Chemica, 10(10): 66-72.
- Li P, Shi L, Gao MN, Yang X, Xue W, Jin LH, Hu DY, Song BA, 2015. Antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives. Bioorganic & Medicinal Chemistry Letters, 25 (3): 481-484.
- Luszczki JJ, Karpińska M, Matysiak J, Niewiadomy A, 2015. Characterization and preliminary anticonvulsant assessment of some 1,3,4-thiadiazole derivatives. Density Functional Theory Study. Pharmacological Reports, 67 (3): 588-592.
- Merrick JP, Moran D, Radom L, 2007. An Evaluation of Harmonic Vibrational Frequency Scale Factors. Journal of Physical Chemistry, 111(45): 11683-11700.
- Mulliken RS, 1955. Electronic Population Analysis on LCAO–MO Molecular Wave Functions I. The Journal of Chemical Physics, 23; 1833-1840.
- Ocak N, Çoruh U, Kahveci B, Şaşmaz S, Vazquez-Lopez EM, Erdönmez A, 2003. 1- Acetyl-3-(p-chlorobenzyl)-4-(p-chlorobenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one. Acta Crystallographica Section E, 59(6): 750-752.
- Polkam N, Kummari B, Rayam P, Brahma U, Naidu VGM, Balasubramanian S, Anireddy JS, 2017. Synthesis of 2,5-Disubstituted-1,3,4-oxadiazole Derivatives and Their Evaluation as Anticancer and Antimycobacterial Agents. Medicinal Chemistry & Drug Discovery, 2: 5492-5496.
- Ragab FA, Heiba HI, El-Gazzar MG, Abou-Seri SM, El-Sabbagh WA, El-Hazek RM, 2016. Anti-inflammatory, analgesic and COX-2 inhibitory activity of novel thiadiazoles in irradiated rats. Journal of Photochemistry and Photobiology B, 166: 285-300.
- Romano E, Ladetto MF, Brandán SA, 2013. Structural and vibrational studies of the potential anticancer agent, 5-difluoromethyl-1,3,4-thiadiazole-2-amino by DFT calculations. Computational and Theoretical Chemistry, 1011: 57-64.
- Shahcheragh SM, Habibi A, Khosravi S, 2017. Straight forward synthesis of novel substituted 1,3,4-thiadiazole derivatives in choline chloride-based deep eutectic solvent. Tetrahedron Letters, 58, 855-859.
- Ustabaş R, Çoruh U, Sancak K, Ünver Y, Vazquez-Lopez EM, 2007. 1-(benzoylmethyl)-4-[(2,4-dichlorobenzylidene)amino]-3-(2-thienylmethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one. Acta Crystallographica Section E, 63: 2982-3051.
- Wolinski K, Hilton JF, Pulay PJ, 1990. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112, 512.
- Zarei M, 2017. One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent. Tetrahedron, 73: 1867-1872.
Yeni 5-Merkapto-2-(5-metil-furan-2-il-metilidenamino)-1,3,4-tiyadiazol Molekülün Sentezi ve Teorik Analizi
Öz
Bu çalışmada, yeni 5-Merkapto-2-(5-metil-furan-2-il-metilidenamino)-1,3,4-tiyadiazol molekülü 5-metil-furan-2-karbaldehid ile 2-amino-5-merkapto-1,3,4- tiyadiazolün reaksiyonundan sentezlenmiştir. 5-Merkapto-2-(5-metil-furan-2-il-metilidenamino)-1,3,4-tiyadiazol DFT(B3LYP)-HF metodları kullanılarak optimize edilmiştir. Molekülün mulliken yükleri, HOMO-LUMO enerjisi, ELUMO-EHOMO enerji farkı(ΔEg), dipol moment, elektron ilgisi (A), iyonizasyon potansiyeli (I), kimyasal yumuşaklık (σ), kimyasal sertlik (η), elektronegativite (χ), bağ açıları, toplam enerjisi ve bağ uzunlukları DFT(B3LYP)-HF metodları ile 6-31G(d,p) temel seti kullanılarak hesaplanmıştır. Ayrıca, 1H-NMR ve 13C-NMR isotropik kayma değerleri GaussianG09W programı ile GIAO metodları kullanılarak hesaplanmıştır. Deneysel ve hesaplanan teorik değerler karşılaştırılmış ve regrasyon analizi yapılmıştır. IR değerlerini belirlemek için veda4f programı kullanılmıştır. DFT-HF metodlarına göre elde edilen IR verileri uygun skala faktörleri ile çarpılmış ve teorik infrared spektrumları çizilmiştir.
Anahtar Kelimeler
Kaynakça
- Dani RK, Bharty MK, Kushawaha SK, Prakash O, Singh RK, Singh NK, 2013. Hydration process as an activation of transand cisplatin complexes in anticancer treatment DFT and ab initio computational study of thermodynamic and kinetic parameters. Journal of Computational Chemistry, 26 (9): 907-914.
- Dennington R, Keith T, Millam J, 2009. GaussView, Version 5, Semichem Inc., Shawnee Mission KS.
- El-Gohary NS, Shaaban MI, 2013. Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles. European Journal of Medicinal Chemistry, 63: 185-195.
- Fukui K, Yonezawa T, Shingu HJ, 1952. A molecular orbital theory of reactivity in aromatic hydrocarbons. The Journal of Chemical Physics. 20: 722-725.
- Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X et al, 2009. Gaussian 09, Revision C.01, Gaussian, Inc. Wallingford, CT.
- Gür M, Muğlu H, Çavuş MS, Güder A, Sayıner HS, Kandemirli F, 2017. Synthesis, characterization, quantum chemical and evaluation of antioxidant properties of 1,3,4-thiadiazole derivatives including 2- and 3-methoxy cinnamic acids. Journal of Molecular Structure, 1134: 40-50. Jamróz MH, 2004. Vibrational Energy Distribution Analysis, VEDA 4 program, Warsaw.
- Kotan G, Özdemir G, Yüksek H, 2018. Investigation of Spectroscopic, Electronic and Geometric Properties of 2-(3-Methyl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethine)-benzoic acid Using B3lyp and Hf Basis Sets. Der Pharma Chemica, 10(10): 66-72.
- Li P, Shi L, Gao MN, Yang X, Xue W, Jin LH, Hu DY, Song BA, 2015. Antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives. Bioorganic & Medicinal Chemistry Letters, 25 (3): 481-484.
- Luszczki JJ, Karpińska M, Matysiak J, Niewiadomy A, 2015. Characterization and preliminary anticonvulsant assessment of some 1,3,4-thiadiazole derivatives. Density Functional Theory Study. Pharmacological Reports, 67 (3): 588-592.
- Merrick JP, Moran D, Radom L, 2007. An Evaluation of Harmonic Vibrational Frequency Scale Factors. Journal of Physical Chemistry, 111(45): 11683-11700.
- Mulliken RS, 1955. Electronic Population Analysis on LCAO–MO Molecular Wave Functions I. The Journal of Chemical Physics, 23; 1833-1840.
- Ocak N, Çoruh U, Kahveci B, Şaşmaz S, Vazquez-Lopez EM, Erdönmez A, 2003. 1- Acetyl-3-(p-chlorobenzyl)-4-(p-chlorobenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one. Acta Crystallographica Section E, 59(6): 750-752.
- Polkam N, Kummari B, Rayam P, Brahma U, Naidu VGM, Balasubramanian S, Anireddy JS, 2017. Synthesis of 2,5-Disubstituted-1,3,4-oxadiazole Derivatives and Their Evaluation as Anticancer and Antimycobacterial Agents. Medicinal Chemistry & Drug Discovery, 2: 5492-5496.
- Ragab FA, Heiba HI, El-Gazzar MG, Abou-Seri SM, El-Sabbagh WA, El-Hazek RM, 2016. Anti-inflammatory, analgesic and COX-2 inhibitory activity of novel thiadiazoles in irradiated rats. Journal of Photochemistry and Photobiology B, 166: 285-300.
- Romano E, Ladetto MF, Brandán SA, 2013. Structural and vibrational studies of the potential anticancer agent, 5-difluoromethyl-1,3,4-thiadiazole-2-amino by DFT calculations. Computational and Theoretical Chemistry, 1011: 57-64.
- Shahcheragh SM, Habibi A, Khosravi S, 2017. Straight forward synthesis of novel substituted 1,3,4-thiadiazole derivatives in choline chloride-based deep eutectic solvent. Tetrahedron Letters, 58, 855-859.
- Ustabaş R, Çoruh U, Sancak K, Ünver Y, Vazquez-Lopez EM, 2007. 1-(benzoylmethyl)-4-[(2,4-dichlorobenzylidene)amino]-3-(2-thienylmethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one. Acta Crystallographica Section E, 63: 2982-3051.
- Wolinski K, Hilton JF, Pulay PJ, 1990. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112, 512.
- Zarei M, 2017. One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent. Tetrahedron, 73: 1867-1872.
Toplam 19 adet kaynakça vardır.
Ayrıntılar
| Birincil Dil | İngilizce |
|---|---|
| Konular | Kimya Mühendisliği |
| Bölüm | Kimya / Chemistry |
| Yazarlar | |
| Yayımlanma Tarihi | 1 Haziran 2019 |
| Gönderilme Tarihi | 19 Mart 2019 |
| Kabul Tarihi | 2 Nisan 2019 |
| Yayımlandığı Sayı | Yıl 2019 Cilt: 9 Sayı: 2 |