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Synthesis, Molecular Structure, Spectral and Electronic Properties of 2-(3-Hydroxy-4-methoxybenzylideneamino)-5-mercapto-1,3,4- thiadiazole Compound

Yıl 2018, Cilt: 8 Sayı: 4, 229 - 238, 30.12.2018
https://doi.org/10.21597/jist.426556

Öz

In this theoretical and experimental study, the geometric parameters (bond lengths and ligand angles), vibrational frequencies, 1H-NMR and 13C-NMR spectral values and nonlinear optical (NLO) properties of the molecule of 2-(3-hydroxy-4-methoxybenzylideneamino)-5-mercapto-1,3,4-thiadiazole have been carried out. Firstly, the 2- (3-hydroxy-4-methoxybenzylideneamino) -5-mercapto-1,3,4-thiadiazole molecule was optimized using the B3LYP/HF 6-311G+(d,p) basic sets. The 1H-NMR and 13C-NMR chemical shift values of the GIAO method were calculated using the Gaussian G09W program package in DMSO phase starting from the optimized structure. Molecular vibration wave numbers were examined by using the basic set of 6-311G+(d,p) according to density function theories using HF and B3LYP standard. FT-IR (100-4000 cm-1) vibration frequencies of the relevant compound were recorded. Vibration frequencies obtained in B3LYP and HF methods were compared with experimental values and it has been observed that the closest results to experimental values were B3LYP data. Additionally, electronic properties such as HOMO and LUMO energies, molecular electrostatic potential, electron affinity, ionization potential, molecular softness, molecular stiffness, electronegativity, dipole moments and total energies of the synthesized new compound were calculated using the same set and methods.

Kaynakça

  • Apaydın F, 1991. Magnetik Rezonans. Hacettepe Üniversitesi, 3: 6-8.
  • Atalay Y, Avcı D, 2007. Theoretical studies of molecular structure and vibrational spectra of melaminium citrate. Spectrochimica Acta Part A, 67: 327–333.
  • Becke AD, 1988. Density-functional exchangeenergy approximation with correct asymptotic behavior. Physical Review A, 3098-3100.
  • Beytur M, 2014. Bazı yeni beş üyeli heterosiklik bileşiklerin sentezi ve bazı özelliklerinin incelenmesi, Kafkas Üniversitesi Fen Bilimleri Enstitüsü, Doktora Tezi, 709s.
  • Boechat, N., Ferreira, S. B., Glidewell, C., Low, J. N., Skakle, J. M., Wardell, S. M. 2006. 2-Amino-5-trifluoromethyl-1,3,4-thiadiazole and a redetermination of 2-amino-1,3,4-thiadiazole, both at 120 K: chains of edge-fused R(2)(2)(8) and R(4)(4)(10) rings, and sheets of R(2)(2)(8) and R(6)(6)(20) rings, Acta Crystallographica Section C, 62: 42-44.
  • Burda JV, Zeizinger M, Leszczynski J, 2005. Hydration process as an activation of trans- and cisplatin complexes in anticancer treatment. DFT and ab initio computational study of thermodynamic and kinetic parameters. Journal of Computational Chemistry, 26 (9): 907-914.
  • Dani RK, Bharty MK, Kushawaha, SK, Prakash O, Singh RK, Singh NK, 2013. Hydration process as an activation of trans- and 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.
  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson G A, 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 J A, Vreven TJ., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin N, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, 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 CJ, Ochterski W, Martin LR, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox D J, 2009. Gaussian Inc., (Wallingford, CT).
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  • Fukui K. 1982, Role of frontier orbitals in chemical reactions, Science, 747-754.
  • Gans P, 1971. Vibrating molecules. Chapman and Hall, 18-59.
  • Gökçe H, Akyıldırım O, Bahçeli S, Yüksek H, Gürsoy Kol O, 2014. The 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]–4,5–dihydro–1H–1,2,4–triazol–5–one molecule investigated by a joint spectroscopic and quantum chemical calculations. Journal of Molecular Structure, 1056-1057: 273–284.
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  • Gür M, Muğlu H, Çavuş MS, Güder A, Sayıner HS, Kandemirli F, 2017. Synthesis, characterization, quantum chemical calculations 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.
  • İkizler AA, 1996. Organik Kimyaya Giriş, Dördüncü Baskı, KTÜ Basımevi, Trabzon, Türkiye, 398s.
  • Jamróz MH, 2004. Vibrational energy distribution analysis: VEDA 4 program, Warsaw.
  • Kadi AA, Al-Abdullah ES, Shehata IA, Habib EE, Ibrahim TM, El-Emam AA, 2010. Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1, 3, 4-thiadiazole derivatives, European journal of medicinal chemistry, 45 (11): 5006-5011.
  • Kaczor AA, Pitucha M, Karczmarzyk Z, Wysocki W, Rzymowska J, Matosiuk D, 2013. Structural and molecular docking studies of 4-benzyl-3-[(1-methylpyrrol- 2-yl)methyl]-4,5-dihydro-1h-1,2,4-triazol-5-one with anticancer activity. Medicinal Chemistry, 9 (3): 313-328.
  • Kaczor AA, Tomasz T, Karczmarzyk Z, Wysocki W, Fruzinski A, Brodacka M, Matosiuk D, Monika M, 2014. Structural Studies on N-(1-naphthyl)-3-amino-5-oxo-4-phenyl-1Hpyrazole- 1-carboxamide with Antibacterial Activity. Letters in Organic Chemistry, 11(1): 40-48.
  • Kurowska A, Kostyuchenko AS, Zassowski P, Skorka L, Yurpalov VL, Fisyuk AS, Pron A, Domagala W, 2014. Symmetrically Disubstituted Bithiophene Derivatives of 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, and 1,2,4-Triazole Spectroscopic, Electrochemical, and Spectroelectrochemical Properties, Journal of Physical Chemistry, 18: 25176-25189.
  • Lee C, Yang W, R. Parr G, 1998. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical Review B, 785-789.
  • Lee SY, 1998. Molecular structure and vibrational spectra of biphenyl in the ground and the lowest triplet states. Density Functional Theory Study, Bulletin of the Korean Chemical Society, 19(1): 93-98.
  • 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.
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  • Mulliken RS, 1955. Electronic population analysis on LCAO–MO molecular wave functions. Journal of Chemical Physics, 23: 1833–1840.
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  • 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.
  • Preat J, Jacquemin D, Wathelet V, Andre JM, Parpete EA, 2006. TD-DFT Investigation of the UV Spectra of Pyranone Derivatives, The Journal of Physical Chemistry A, 110 (26): 8144-8150.
  • 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.
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  • Shahcheragh, S. M., Habibi, A., Khosravi, S. 2017. Straightforward synthesis of novel substituted 1,3,4-thiadiazole derivatives in choline chloride-based deep eutectic solvent, Tetrahedron Letters 58, 855-859.
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2-(3-Hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4- tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral ve Elektronik Özelliklerinin İncelenmesi

Yıl 2018, Cilt: 8 Sayı: 4, 229 - 238, 30.12.2018
https://doi.org/10.21597/jist.426556

Öz

Bu çalışmada, 2-(3-hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4-tiyadiazol molekülünün geometrik parametreleri (bağ uzunlukları ve bağ açıları), titreşim frekansları, 1H-NMR ve 13C-NMR spektral değerleri ve doğrusal olmayan optik (NLO) özellikleri üzerine teorik ve deneysel bir çalışma gerçekleştirilmiştir. Öncelikle, 2-(3-hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4-tiyadiazol B3LYP/HF 6-311G+(d,p) temel setleri kullanılarak optimize edilmiştir. GIAO yöntemine göre 1H-NMR ve 13C-NMR kimyasal kayma değerleri optimize edilmiş yapıdan başlanarak DMSO fazında Gaussian G09W program paketi kullanılarak hesaplanmıştır. Molekülün titreşim dalga sayıları HF ve B3LYP standardı kullanılarak yoğunluk fonksiyonu teorilerine göre 6-311G+(d,p) temel seti vasıtasıyla incelenmiştir. İlgili bileşiğin FT-IR (100-4000 cm-1) titreşim frekansları kaydedilmiştir. B3LYP ve HF yöntemlerinde elde edilen titreşim frekansları deneysel değerler ile mukayese edilmiş ve deneysel değerlere en yakın sonuçların B3LYP verilerinin olduğu gözlemlenmiştir. Ek olarak, sentezlenmiş yeni bileşiğin HOMO ve LUMO enerjileri, moleküler elektrostatik potansiyeli, elektron ilgisi, iyonlaşma potansiyeli, moleküler yumuşaklık, moleküler sertlik, elektronegatiflik, dipol momentleri ve toplam enerjileri gibi elektronik özellikleri aynı set ve yöntemler kullanılarak hesaplanmıştır.

Kaynakça

  • Apaydın F, 1991. Magnetik Rezonans. Hacettepe Üniversitesi, 3: 6-8.
  • Atalay Y, Avcı D, 2007. Theoretical studies of molecular structure and vibrational spectra of melaminium citrate. Spectrochimica Acta Part A, 67: 327–333.
  • Becke AD, 1988. Density-functional exchangeenergy approximation with correct asymptotic behavior. Physical Review A, 3098-3100.
  • Beytur M, 2014. Bazı yeni beş üyeli heterosiklik bileşiklerin sentezi ve bazı özelliklerinin incelenmesi, Kafkas Üniversitesi Fen Bilimleri Enstitüsü, Doktora Tezi, 709s.
  • Boechat, N., Ferreira, S. B., Glidewell, C., Low, J. N., Skakle, J. M., Wardell, S. M. 2006. 2-Amino-5-trifluoromethyl-1,3,4-thiadiazole and a redetermination of 2-amino-1,3,4-thiadiazole, both at 120 K: chains of edge-fused R(2)(2)(8) and R(4)(4)(10) rings, and sheets of R(2)(2)(8) and R(6)(6)(20) rings, Acta Crystallographica Section C, 62: 42-44.
  • Burda JV, Zeizinger M, Leszczynski J, 2005. Hydration process as an activation of trans- and cisplatin complexes in anticancer treatment. DFT and ab initio computational study of thermodynamic and kinetic parameters. Journal of Computational Chemistry, 26 (9): 907-914.
  • Dani RK, Bharty MK, Kushawaha, SK, Prakash O, Singh RK, Singh NK, 2013. Hydration process as an activation of trans- and 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.
  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson G A, 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 J A, Vreven TJ., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin N, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, 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 CJ, Ochterski W, Martin LR, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox D J, 2009. Gaussian Inc., (Wallingford, CT).
  • Fessenden RJ, Fessenden JS, 1986. “Organic Chemistry”, Third Edition, Brooks, Cole Publishing Company, California.
  • Fukui K. 1982, Role of frontier orbitals in chemical reactions, Science, 747-754.
  • Gans P, 1971. Vibrating molecules. Chapman and Hall, 18-59.
  • Gökçe H, Akyıldırım O, Bahçeli S, Yüksek H, Gürsoy Kol O, 2014. The 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]–4,5–dihydro–1H–1,2,4–triazol–5–one molecule investigated by a joint spectroscopic and quantum chemical calculations. Journal of Molecular Structure, 1056-1057: 273–284.
  • Grykien R, Luszczynska B, Glowacki I, Kurach E, Rybakiewicz R, Kotwica K, Zagorska M, Pron A, Tassini P, Maglione MG, Del Mauro AG, Fasolino T, Rega R, Pandolfi G, Minarini C, Aprano S. 2014. Photo- and electroluminescent properties of bithiophene disubstituted 1,3,4-thiadiazoles and their application as active components in organic light emitting diodes, Optical Materials, 37: 193-199.
  • Gümüş PH, Tamer Ö, Avcı D, Atalay Y, 2015. 4-(Metoksimetil)-1,6-dimetil-2-okso-1,2-dihidropiridin-3-karbonitril molekülünün teorik olarak incelenmesi. Sakarya Üniversitesi Fen Bilimleri Dergisi, 3: 303-311.
  • Gündüz B, Al-Ghamdi AA, Hendi AA, Gafer ZH, El-Gazzar S, El-Tantawy F, Yakuphanoglu F, 2014. New Schottky diode based entirely on nickel aluminate spinel/p-silicon using the sol-gel spin coating approach, Superlattices and Microstructures, 64: 167-177.
  • Gür M, Muğlu H, Çavuş MS, Güder A, Sayıner HS, Kandemirli F, 2017. Synthesis, characterization, quantum chemical calculations 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.
  • İkizler AA, 1996. Organik Kimyaya Giriş, Dördüncü Baskı, KTÜ Basımevi, Trabzon, Türkiye, 398s.
  • Jamróz MH, 2004. Vibrational energy distribution analysis: VEDA 4 program, Warsaw.
  • Kadi AA, Al-Abdullah ES, Shehata IA, Habib EE, Ibrahim TM, El-Emam AA, 2010. Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1, 3, 4-thiadiazole derivatives, European journal of medicinal chemistry, 45 (11): 5006-5011.
  • Kaczor AA, Pitucha M, Karczmarzyk Z, Wysocki W, Rzymowska J, Matosiuk D, 2013. Structural and molecular docking studies of 4-benzyl-3-[(1-methylpyrrol- 2-yl)methyl]-4,5-dihydro-1h-1,2,4-triazol-5-one with anticancer activity. Medicinal Chemistry, 9 (3): 313-328.
  • Kaczor AA, Tomasz T, Karczmarzyk Z, Wysocki W, Fruzinski A, Brodacka M, Matosiuk D, Monika M, 2014. Structural Studies on N-(1-naphthyl)-3-amino-5-oxo-4-phenyl-1Hpyrazole- 1-carboxamide with Antibacterial Activity. Letters in Organic Chemistry, 11(1): 40-48.
  • Kurowska A, Kostyuchenko AS, Zassowski P, Skorka L, Yurpalov VL, Fisyuk AS, Pron A, Domagala W, 2014. Symmetrically Disubstituted Bithiophene Derivatives of 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, and 1,2,4-Triazole Spectroscopic, Electrochemical, and Spectroelectrochemical Properties, Journal of Physical Chemistry, 18: 25176-25189.
  • Lee C, Yang W, R. Parr G, 1998. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical Review B, 785-789.
  • Lee SY, 1998. Molecular structure and vibrational spectra of biphenyl in the ground and the lowest triplet states. Density Functional Theory Study, Bulletin of the Korean Chemical Society, 19(1): 93-98.
  • 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 A, 111(45): 11683-11700.
  • Mulliken RS, 1955. Electronic population analysis on LCAO–MO molecular wave functions. Journal of Chemical Physics, 23: 1833–1840.
  • Pitucha, M., Karczmarzyk, Z., Wysocki, W., Kaczor, A. A., Matosiuk, D. 2011. Experimental and theoretical investigations on the keto–enol tautomerism of 4-substituted 3-[1-methylpyrrol-2-yl)methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Journal of Molecular Structure, 994: 313-320.
  • 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.
  • Preat J, Jacquemin D, Wathelet V, Andre JM, Parpete EA, 2006. TD-DFT Investigation of the UV Spectra of Pyranone Derivatives, The Journal of Physical Chemistry A, 110 (26): 8144-8150.
  • 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, S. M., Habibi, A., Khosravi, S. 2017. Straightforward synthesis of novel substituted 1,3,4-thiadiazole derivatives in choline chloride-based deep eutectic solvent, Tetrahedron Letters 58, 855-859.
  • Shokhmkar M, Raissi H, Mollania F, 2014. Molecular structure, conformational stability, energetic and intramolecular hydrogen bonding in ground, and electronic excited state of 3-mercapto propeneselenal. Structural Chemistry, 25 (4): 1153-1164.
  • Tamer Ö, Avcı D, Atalay Y, 2015. The effects of electronegative substituent atoms on structural, vibrational, electronic and NLO properties of some 4-nitrostilbene derivates. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 136: 644–650.
  • Thanigaimani K, Khalib NC, Temel E, Arshad S, Razak IA, 2015. Hydration process as an activation of trans- and cisplatin complexes in anticancer treatment. DFT and ab initio computational study of thermodynamic and kinetic parameters. Journal of Molecular Structure, 1099: 246-256.
  • Toledo TA, Costa RC, Silva LE, Teixeira AMR, Lima VN, Sena DM, Coutinho HDM, Freire PTCR, Pizani PS, 2016. Thermal and biological properties of the Schiff base N,N0-bis(salicylidene)-1,2-phenylenediamine, a potential adjuvant to antibiotic therapy. Journal of Molecular Structure, 1115: 105-108.
  • Toledo TA, Costa RC, Al-Maqtari HM, Jamalis J, Pizani PS, 2017. Temperature dependence of the Raman spectrum of 1-(4-chlorophenyl)-3-(2-thienyl)prop-2-en-1-one. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 180: 9-17.
  • Turhan Irak Z, Gümüş S, (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7):80-89.
  • Uğurlu G, Yüksek H, Beytur M, Necefoğlu H, 2016. Theoretical molecular structure, NLO, NMR and HOMO-LUMO analysis of isonicotinic acid (ortho-, meta- and para-hydroxy-benzylidene)-hydrazides. International Journal of Thales Natural Sciences, 1(2) :1-9.
  • Wolinski K, Hilton JF, Pulay P, 1990. Journal of the American Chemical Society, 112; 8251.
  • Yusuf M, Khan RA, Ahmed B, 2008. Syntheses and anti-depressant activity of 5-amino-1,3,4-thiadiazole-2-thiol imines and thiobenzyl derivatives. Bioorganic & Medicinal Chemistry Letters, 16: 8029-8034.
  • Yüksek H, Çakmak İ, Sadi S, Alkan M, 2005. Synthesis and GIAO NMR Calculations for Some Novel 4-Heteroarylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1H and 13C Chemical Shifts. International Journal of Molecular Sciences, 6; 219-229.
  • Zarei M, 2017. One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent, Tetrahedron, 73: 1867-1872.
  • Zou XJ, Lai LH, Jin GY, Zhang ZX, 2002. Synthesis, fungicidal activity, and 3D-QSAR of pyridazinone-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles, Journal of Agricultural and Food Chemistry, 50 (13): 3757-3760.
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  • Zyss J, 1994. Molecular Non linear Optics: materials, physics and devices, Academic Press, Boston.
Toplam 50 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Kimya / Chemistry
Yazarlar

Murat Beytur 0000-0002-7098-5592

Onur Akyıldırım 0000-0003-1090-695X

Sevda Manap 0000-0002-5025-9622

Haydar Yüksek Bu kişi benim 0000-0003-1289-1800

Yayımlanma Tarihi 30 Aralık 2018
Gönderilme Tarihi 23 Mayıs 2018
Kabul Tarihi 5 Eylül 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 8 Sayı: 4

Kaynak Göster

APA Beytur, M., Akyıldırım, O., Manap, S., Yüksek, H. (2018). 2-(3-Hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4- tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral ve Elektronik Özelliklerinin İncelenmesi. Journal of the Institute of Science and Technology, 8(4), 229-238. https://doi.org/10.21597/jist.426556
AMA Beytur M, Akyıldırım O, Manap S, Yüksek H. 2-(3-Hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4- tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral ve Elektronik Özelliklerinin İncelenmesi. Iğdır Üniv. Fen Bil Enst. Der. Aralık 2018;8(4):229-238. doi:10.21597/jist.426556
Chicago Beytur, Murat, Onur Akyıldırım, Sevda Manap, ve Haydar Yüksek. “2-(3-Hidroksi-4-Metoksibenzilidenamino)-5-Merkapto-1,3,4- Tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral Ve Elektronik Özelliklerinin İncelenmesi”. Journal of the Institute of Science and Technology 8, sy. 4 (Aralık 2018): 229-38. https://doi.org/10.21597/jist.426556.
EndNote Beytur M, Akyıldırım O, Manap S, Yüksek H (01 Aralık 2018) 2-(3-Hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4- tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral ve Elektronik Özelliklerinin İncelenmesi. Journal of the Institute of Science and Technology 8 4 229–238.
IEEE M. Beytur, O. Akyıldırım, S. Manap, ve H. Yüksek, “2-(3-Hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4- tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral ve Elektronik Özelliklerinin İncelenmesi”, Iğdır Üniv. Fen Bil Enst. Der., c. 8, sy. 4, ss. 229–238, 2018, doi: 10.21597/jist.426556.
ISNAD Beytur, Murat vd. “2-(3-Hidroksi-4-Metoksibenzilidenamino)-5-Merkapto-1,3,4- Tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral Ve Elektronik Özelliklerinin İncelenmesi”. Journal of the Institute of Science and Technology 8/4 (Aralık 2018), 229-238. https://doi.org/10.21597/jist.426556.
JAMA Beytur M, Akyıldırım O, Manap S, Yüksek H. 2-(3-Hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4- tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral ve Elektronik Özelliklerinin İncelenmesi. Iğdır Üniv. Fen Bil Enst. Der. 2018;8:229–238.
MLA Beytur, Murat vd. “2-(3-Hidroksi-4-Metoksibenzilidenamino)-5-Merkapto-1,3,4- Tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral Ve Elektronik Özelliklerinin İncelenmesi”. Journal of the Institute of Science and Technology, c. 8, sy. 4, 2018, ss. 229-38, doi:10.21597/jist.426556.
Vancouver Beytur M, Akyıldırım O, Manap S, Yüksek H. 2-(3-Hidroksi-4-metoksibenzilidenamino)-5-merkapto-1,3,4- tiyadiazol Bileşiğinin Sentezi, Moleküler Yapısı, Spektral ve Elektronik Özelliklerinin İncelenmesi. Iğdır Üniv. Fen Bil Enst. Der. 2018;8(4):229-38.