Theoretical investigation on the structural and electronic properties of (1-naphthylmethylidene)isonicotinohydrazide molecule

Year 2018, , 167 - 177, 30.06.2018

Güventürk Uğurlu , Hacali Necefoğlu

https://doi.org/10.21597/jist.428365

Abstract

In this paper, in order to determine the stable conformers of (1-naphthylmethylidene)

isonicotinohydrazide molecule (I), the conformational analysis of the molecule studied was investigated by Density

Functional Theory (DFT/B3LYP) levels of theory using 6-311++G (d,p) basis set. The two stable states conformers

(C-I and C-II) of the this molecule have been found and these conformers were optimized HF/ 6-311++G(d,p)

and B3LYP/ 6-311++G(d,p) levels of theory and basis set. The computational results have shown that the most

stable conformer of molekülünün I was as the C-I form. The dipole moment (µ), polarizability (α) and first order

hyperpolarizability (β), the highest occupied molecular orbital energies (), the lowest unoccupied molecular orbital

energies (ELUMO) and energy gap () of C-I and C-II conformers have been calculated by using 6-311++G (d, p)

basis set for both models at the ground state. The hardness (η) and electronegativity (χ) parameters were determined

taking into account these energy values. Besides, 1H-NMR and 13C-NMR chemical shift values according to the

method GIAO by obtained the optimized structure were calculated using B3LYP/311++G (2d,p) and HF/6-31G

levels of theory. The dipole moment values for C-I and C-II conformers are calculated at 2.05 and 2.32 with

DFT/B3LYP level of the theory 6-311++G (d, p) basis set and at the HF/6-311++G(d,p) 1.94, and 2.32 Debye,

respectively. The structural parameters of molekülünün I compared with data in the literature.

Keywords

DFT/B3LYP, HF, hyperpolarizability, (1-naphthylmethylidene)isonicotinohydrazide, polarizability

(1-naftilmetiliden)izonikotinohidrazid molekülünün yapısal ve elektronik özelliklerinin teorik olarak incelenmesi

Abstract

Bu çalışmada, (1-naftilmetiliden)izonikotinohidrazid molekülünün (I) kararlı konformerlerini belirlemek

için, çalışılan molekülün konformasyon analizi Yoğunluk Fonksiyonel Teorisi (DFT/B3LYP) metodu ile

6-311++G(d,p) temel seti kullanılarak incelendi. Bu molekülün iki kararlı durum konformerleri (C-I ve C-II)

bulundu ve bu konformerler Hartree Fock HF/6-311++G(d,p) ve B3LYP/6-311++G(d,p) teori düzeyinde ve temel

seti ile optimize edildi. Hesaplama sonuçları, I molekülünün en kararlı konformerinin C-I olduğunu gösterdi. Taban

durumundaki C-I ve C-II konformerler için, dipol moment (μ), polarizebilite (α), birinci-derece hiperpolarizebilite

(β), en yüksek dolu molekül orbital enerjileri (), en düşük boş molekül orbital enerjileri () ve enerji farkı () her

iki modelde 6-311++G (d,p) taban seti kullanılarak hesaplanmıştır. Bu enerjiler dikkate alınarak sertlik (η) ve

elektronegatiflik (χ) parametreleri hesaplandı. Ayrıca, elde edilen optimize yapı ile GIAO yöntemine göre 1H-NMR

ve 13C-NMR kimyasal kayma değerleri B3LYP / 311 + + G (2d, p) ve Hartree Fock HF / 6-31G teori düzeyinde

hesaplandı. C-I ve C-II konformerleri için dipol moment değerleri, sırasıyla B3LYP / 6-311 ++ G (d, p) ile 2.05

ve 2.32 ve HF / 6-311 ++ G (d, p) 1.94 ve 2.32 Debye bulundu. I molekülünün yapısal parametreleri, literatürdeki

verilerle karşılaştırıldı.

Keywords

DFT/B3LYP, HF, hiperpolarizebilite, (1-naftilmetiliden)izonikotinohidrazid, polarizebilite.

References

• Bayrak H, Demirbaş A, Demirbaş N, Karaoğlu SA, 2009. Synthesis of some new 1, 2, 4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. European Journal of Medicinal Chemistry, 44: 4362-4366.
• Becke AD, 1988. Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6):3098–310
• Becke AD, 1993 Density-functional thermochemistry 3. the role of exact exchange. The Journal of Chemical Physics, 98 (7): 5648-5652.
• Bhat MA, Abdel-Aziz HA, Ghabbour HA, Hemamalini M, Fun HK, 2012. (E)-N′-(4-Iso­propyl­benzyl­idene)isonicotinohydrazide monohydrate. Acta Crystallographica, 68: 1002.
• Bloom BR, Murray CJL, 1992. Tuberculosis: Commentary on a reemergent killer. Science, 257: 1055-1064.
• Bottari B, Maccari R, Monforte F, Ottanà R, Vigorita MG, Bruno G, Nicolò F, Rotondo A, Rotondo E, 2001. Nickel (II) 2, 6-diacetylpyridine bis (isonicotinoylhydrazonate) and bis (benzoylhydrazonate) complexes: structure and antimycobacterial evaluation. Part XI. Bioorganic & Medicinal Chemistry, 9: 2203–2211.
• Dennington R, Keith T, Millam J, 2009. Semichem Inc., GaussView, Version 5, Shawnee Mission KS,
• Francl MM, Pietro WJ, Hehre WJ, Binkley JS, Gordon, MS, DeFrees DJ, Pople, JA, 1982. Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements. Chemical Physics, 77: 3654-3665
• 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 JA, 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, 2010. Gaussian Inc., (Wallingford, CT).
• Johnson K, Schultz PG, 1994. Mechanistic studies of the oxidation of isoniazid by the catalase peroxidase from Mycobacterium tuberculosis. Journal of the American Chemical Society, 116: 7425-7426.
• Judge V, Narasimhan B, Ahuja M, Sriram D, Yogeeswari P, De Clercq E, Pannecouque C, Balzarni J, 2012. Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity, and QSAR studies. Medicinal Chemistry Research, 21: 1451-1470.
• Kelode SR, 2013. Thermal and antibacterial studies of cobalt(II), nickel(II), copper(II) and zinc(II) complexes of hydrazone Schiff base. Journal of Chemical and Pharmaceutical Research, 5(6): 60-63.
• Krishnan R, Binkley JS, Seeger R, Pople JA, 1980. Self-consistent molecular-orbital methods. basis set for correlated wave-functions, The Journal of Chemical Physics, 72: 650–654.
• Kriza A, Ababei LV, Cioatera N, Rău I, Stănică N, 2010. Synthesis and structural studies of complexes of Cu, Co, Ni and Zn with isonicotinic acid hydrazide and isonicotinic acid (1-naphthylmethylene)hydrazide. Journal of the Serbian Chemical Society, 75(2): 229–242.
• Lee CT, Yang WT, Parr RG, 1988. Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37: 785-789.
• Maccari R, Ottanà R, Monforte F, Vigorita MG, 2002. In-Vitro antimycobacterial activities of 2-monosubstituted isonicotinohydrazides and their cyanoborane adducts. Antimicrobial Agents and Chemotherapy, 46: 294-299.
• McLean AD, Chandler GS, 1980. Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18. The Journal of Chemical Physics, 72: 5639–5648.
• Moller C, Plesset MS, 1934. Note on an approximation treatment for many- electron systems. Physical Review, 46: 618-622.
• Naveenkumar HS, Sadikun A, Ibrahim P, Loh WS, Fun HK, 2009. (E)-N'-(2,4,5-Trimethoxy­benzyl­idene)isonicotinohydrazide dihydrate. Acta Crystallographica, 65: 2540-2541.
• Prasad S, Agarwal RK, 2009. Synthesis, physico-chemical and biological Properties of complexes of cobalt(II) derived from hydrazones of isonicotinic acid hydrazide Journal of the Korean Chemical Society, 53: 17-26.
• Qurban SW, 2011. Synthesis and characterization of some transition metal complexes of Schiff base derived from isonicotinic hydrazide and O-Vanillin. Diyala Journal for Pure Sciences, 7(2): 94-104.
• Rassolov VA, Ratner MA, Pople JA, Redfern PC, Curtiss LA, 2001. 6–31G* basis set for third-row atoms. Journal of Computational Chemistry, 22: 976–984.
• Sangeetha CC, Madivanane R, Pouchaname V, Vijaya Prasath R, 2014. Experimental (FT-IR & FT - Raman) and theoretical investigation, electronic properties of quinoxaline. International Journal of ChemTech Research, 6 (5): 2854–2865.
• Sbarbaro JA, 1997. Multidrug-resistant tuberculosis. It is time to focus on the private sector of medicine. Chest, 111: 1149-1151.
• Slayden RA, Barry CE, 2000. The genetics and biochemistry of isoniazid resistance in mycobacterium tuberculosis. Microbes and Infection, 2: 659–669.
• Shoeb HA, Bowman BU, Ottoleghi AC, Merola AJ, 1985. Peroxidase-mediated oxidatıon of isoniazıd. Antimicrobial Agents and Chemotherapy, 27: 399-403.
• Sriram D, Yogeeswari P, Priya DY, 2009. Antimycobacterial activity of novel N-(substituted)-2-isonicotinoylhydrazinocarbothioamide endowed with high activity towards isoniazid resistant tuberculosis. Biomedicine & Pharmacotherapy, 63: 36-39.
• Tajudeen SS, Kannappan G, 2013. Synthetic, structural and pharmacological studies on some isonicotinohydrazide and benzohydrazide analogues. Journal of Pharmacy Research, 7: 534-539.
• Yu M, Chen X, Jing ZL, 2005. Isonicotinic acid (2-hydroxy-3-meth­oxybenzyl­idene) hydrazide. Acta Crystallographica, 61: 1345-1346.
• Wahab HA, Choong YS, Ibrahim P, Sadikun A, Scior T, 2009. Elucidating Isoniazid Resistance Using Molecular Modeling. Journal of Chemical Information and Modeling, 49: 97–107.
• Zhang Y, Heym B, Allen B, Young D, Cole S, 1992. The catalase-peroxidase gene and isoniazid resistance of Mycobacterium tuberculosis. Nature, 358: 591-593.