THEORETICAL CONFORMATIONAL ANALYSIS OF 8-(P-TOLYL)NAPHTHALEN-1-OL

Yıl 2013, Sayı: 030, 1 - 8, 15.04.2013

Mahir Tursun , Nesrin Emir İmren Sivrikaya Barış Can Palas

Öz

Theoretical conformational analysis of 8-(p-tolyl)naphthalen-1-ol (8tn) has been performed in terms of

semiempirical (AM1, PM3 and PM6), ab-initio Hartree Fock (HF) and density functional theory (DFT:

B-LYP, B-P86, B3-PW91, B3-LYP) methods with the 6-31G(d) and 6-31++G(d) basis sets. Regarding all

the calculations, C1 form of 8tn (C17H14O) seems energetically more favorable and the lowest energy case

for the optimized structures have been obtained with B3LYP/6-31++G(d) level.

Anahtar Kelimeler

8-(p-tolyl)naphthalen-1-ol, Naphthalene derivatives, Molecular structure, DFT

8-(P-TOLYL)NAFTALİN-1-OL MOLEKÜLÜNÜN KURAMSAL KONFORMASYON ANALİZİ

Öz

8-(P-Tolyl)Naftalin-1-Ol (8tn) molekülünün kuramsal konformasyon analizi 6-31G(d) ve 6-31++G(d) baz

setleri kullanılarak yarı deneysel (AM1, PM3 ve PM6), ab-initio Hartree Fock (HF) ve yoğunluk

fonksiyonel teori (DFT: B-LYP, B-P86, B3-PW91, B3-LYP) yöntemleri ile incelenmektedir. Tüm

hesaplamalara göre 8tn (C17H14O) molekülünün enerji olarak en tercih edilebilir formu C1 olarak

görülmekte ve optimize yapı için en düşük enerji B3LYP/6-31++G(d) yöntemi ile elde edilmektedir.

Anahtar Kelimeler

8-(p-tolyl)naftalin-1-ol, Naftalin türevleri, Moleküler yapı, DFT

Kaynakça

• [1] M. Talukder, C.R. Kates, ‘‘Naphthalene Derivatives’’, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley - Sons, New York, (2001).
• [2] Y.B. Rokade, R.Z. Sayyed, ‘‘Naphthalene derivatives: A new range of antimicrobials with high therapeutic value’’, Rasayan J. Chem. 2: 972, (2009).
• [3] R.S. Upadhayaya, J.K. Vandavasi, R.A. Kardile, S.V. Lahore, S.S. Dixit, H.S. Deokar, P.D. Shinde, M.P. Sarmah, J. Chattopadhyaya, ‘‘Novel quinoline and naphthalene derivatives as potent antimycobacterial agents’’, Eur. J. Med. Chem. 45: 1854, (2010).
• [4] J.C. Cadman, S. J. Coles, A.K. Croft, J.G. Frey, G.J. Tizzard, University of Southampton, Crystal Structure Report Archive, doi:10.3737/ecrystals.chem.soton.ac.uk/1343, (2010).
• [5] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, ‘‘Gaussian 09 Revision A.01’’, (2009).
• [6] R.D. Dennington, T. A. Keith, J. M. Millam, GaussView 5.0.8, Gaussian Inc., (2008).
• [7] C. Parlak, “Theoretical and experimental vibrational spectroscopic study of 4-(1-Pyrrolidinyl)piperidine”, J. Mol. Struct. 966: 1, (2010).
• [8] Ö. Alver, C. Parlak, ‘‘Vibrational spectroscopic investigation and conformational analysis of 1- cyclohexylpiperazine’’, J. Mol. Struct., 975: 85, (2010).z
• [9] Ö. Alver, C. Parlak, ‘‘Vibrational spectroscopic investigation and conformational analysis of 1- pentylamine: A comparative density functional study’’, Journal of Theoretical and Computational Chemistry, 9: 667, (2010).
• [10] Ö. Alver, C. Parlak, ‘‘DFT, FT-Raman, FT-IR, liquid and solid state NMR studies of 2,6- dimethoxyphenyl-boronic acid’’, Vibrational Spectroscopy, 54: 1, (2010).