Abstract
The Schiff base compound, 2-[(4-Fluorophenylimino)methyl]-3,5-dimethoxyphenol, has been synthesized and characterized by IR, electronic spectroscopy, and X-ray single-crystal determination. Molecular geometry from X-ray experiment of the title compound in the ground state have been compared using the Hartree-Fock (HF) and density functional method (B3LYP) with 6–31G(d) basis set. Calculated results show that density functional theory (DFT) and HF can well reproduce the structure of the title compound. The energetic behavior of the title compound in solvent media has been examined using B3LYP method with the 6–31G(d) basis set by applying the polarizable continuum model (PCM). The total energy of the title compound decrease with the increasing polarity of the solvent. By using TD-DFT and TD-HF methods, electronic absorption spectra of the title compound have been predicted and a good agreement with the TD-DFT method and the experimental ones is determined. In addition, DFT calculations of the title compound, molecular electrostatic potential (MEP), natural bond orbital (NBO), and thermodynamic properties were performed at B3LYP/6–31G(d) level of theory.
Similar content being viewed by others
References
Barton D, Ollis WD (1979) Comprehensive Organic Chemistry, vol 2. Pergamon, Oxford
Layer RW (1963) Chem Rev 63:489–510
Ingold CK (1969) Structure and Mechanism in Organic Chemistry, 2nd edn. Cornell Univ, Ithaca
Taggi AE, Hafez AM, Wack H, Young B, Ferraris D, Lectka T (2002) J Am Chem Soc 124:6626–6635
Novopoltseva OM (1995) Cand Sci (Chem). Dissertation, Volgograd
Cohen MD, Schmidt GMJ, Flavian S (1964) J Chem Soc 2041–2051
Hadjoudis E, Vitterakis M, Mavridis IM (1987) Tetrahedron 43:1345–1360
Xu XX, You XZ, Sun ZF, Wang X, Liu HX (1994) Acta Crystallogr A C50:1169–1171
Alarcon SH, Pagani D, Bacigalupo J, Olivieri AC (1999) J Mol Struct 475:233–240
Köysal Y, Işık Ş, Ağar E (2007) Acta Crystallogr E63:o4916
Özek A, Büyükgüngör O, Albayrak Ç, Odabaşoğlu M (2009) Acta Crystallogr E65:o791
Kılıç I, Ağar E, Erşahin F, Işık Ş (2009) Acta Crystallogr E65:o934
Temel E, Albayrak Ç, Odabaşoğlu M, Büyükgüngör O (2007) Acta Crystallogr E63:o374–376
Özek A, Albayrak Ç, Odabaşoğlu M, Büyükgüngör O (2007) Acta Crystallogr C63:o177–o180
Karabıyık H, Ocak İskeleli N, Petek H, Albayrak Ç, Ağar E (2008) J Mol Struct 873:130–136
Koşar B, Büyükgüngör O, Albayrak Ç, Odabaşoğlu M (2004) Acta Crystallogr C60:o458–o460
Tanak H, Erşahin F, Ağar E, Büyükgüngör O, Yavuz M (2008) Anal Sci 24:237–238
Zhang Y, Guo ZJ, You XZ (2001) J Am Chem Soc 123:9378–9387
Proft FD, Geerlings P (2001) Chem Rev 101:1451–1464
Fitzgerald G, Andzelm J (1991) J Phys Chem 95:10531–10534
Ziegler T (1991) Pure Appl Chem 63:873–878
Andzelm J, Wimmer E (1992) J Chem Phys 96:1280–1303
Scuseria GE (1992) J Chem Phys 97:7528–7530
Dickson RM, Becke AD (1993) J Chem Phys 99:3898–3905
Johnson BG, Gill PMW, Pople JA (1993) J Chem Phys 98:5612–5626
Jian FF, Zhao PS, Bai ZS, Zhang L (2005) Struct Chem 16:635–639
Schlegel HB (1982) J Comput Chem 3:214–218
Peng C, Ayala PY, Schlegel HB, Frisch MJ (1996) J Comput Chem 17:49–56
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision E.01. Gaussian Inc, Wallingford
Foresman JB, Frisch A (1996) Exploring chemistry with electronic structure methods, 2nd edn. Gaussian Inc, Pittsburgh
Frisch A, Dennington R II, Keith T, Millam J, Nielsen AB, Holder AJ, Hiscocks J (2007) GaussView Reference, Version 4.0. Gaussian Inc, Pittsburgh
Miertus S, Scrocco E, Tomasi J (1981) Chem Phys 55:117–129
Barone V, Cossi M (1998) J Phys Chem A 102:1995–2001
Cossi M, Rega N, Scalmani G, Barone V (2003) J Comput Chem 24:669–681
Tomasi J, Mennucci B, Cammi R (2005) Chem Rev 105:2999–3094
Runge E, Gross EKU (1984) Phys Rev Lett 52:997–1000
Stratmann RE, Scuseria GE, Frisch MJ (1998) J Chem Phys 109:8218–8224
Bauernschmitt R, Ahlrichs R (1996) Chem Phys Lett 256:454–464
Casida ME, Jamorski C, Casida KC, Salahub DR (1998) J Chem Phys 108:4439–4449
Politzer P, Murray J (2002) Theor Chem Acc 108:134–142
Moustakali-Mavridis I, Hadjoudis E, Mavridis A (1978) Acta Crystallogr B34:3709–3715
Bernstein J, Davies RE, Shimoni L, Chang NL (1995) Angew Chem Int Ed Engl 34:1555–1573
Teimouri A, Emami M, Chermahini AN, Dabbagh HA (2009) Spectrochim Acta Part A 71:1749–1755
Yeap GY, Ha ST, Ishizawa N, Suda K, Boey PL, Mahmood WAK (2003) J Mol Struct 658:87–99
Ünver H, Yildiz M, Kiraz A, Özgen Ö (2009) J Chem Crystallogr 39:17–23
Abkowicz-Bienko AJ, Bienko DC, Latajka Z (2000) J Mol Struct 552:165–175
Masternak A, Wenska G, Milecki J, Skalski B, Franzen S (2005) J Phys Chem 109:759–766
Le Y, Chen JF, Pu M (2008) Int J Pharm 358:214–218
Ledbetter JW Jr (1968) J Phys Chem 72:4111–4115
Dudek GO, Dudek EP (1966) J Am Chem Soc 88:2407–2412
Salman SR, Shawkat SH, Al-Obaidi GM (1989) Spectrosc Lett 22:1265–1273
Yıldız M, Kılıç Z, Hökelek T (1998) J Mol Struct 441:1–10
Nazır H, Yıldız M, Yılmaz H, Tahir MN, Ülkü D (2000) J Mol Struct 524:241–250
Ünver H, Yıldız M, Zengin DM, Özbey S, Kendi E (2001) J Chem Crystallogr 31:211–216
Salman SR, Kamounah FS (2002) Spectrosc Lett 35:327–335
Yıldız M (2004) Spectrosc Lett 37:367–381
Dziembowska T, Jogodzinska E, Rozwadowski Z, Kotfica M (2001) J Mol Struct 598:229–234
Rong ZC, Jiang LZ, Hong CY, Shan CH, Zhi Wu Y, Hua YL (2009) THEOCHEM 899:86–93
Scrocco E, Tomasi J (1978) Adv Quantum Chem 11:115–121
Luque FJ, Lopez JM, Orozco M (2000) Theor Chem Acc 103:343–345
Politzer P, Laurence PR, Jayasuriya K, McKinney J (1985) Special issue of Environ Health Perspect 61:191–202
Scrocco E, Tomasi J (1973) Topics in Current Chemistry, vol. 7. Springer Verlag, Berlin, p 95
Politzer P, Truhlar DG (1981) Chemical Applications of Atomic and Molecular Electrostatic Potentials. Plenum, New York
Hussein W, Walker CG, Peralta-Inga Z, Murray JS (2001) Int J Quantum Chem 82:160–169
Politzer P, Concha MC, Murray JS (2000) Int J Quantum Chem 80:184–192
Özdemir N, Dinçer M, Çukurovalı A (2009) J Mol Model. doi:10.1007/s00894-009-0552-8
Schwenke DW, Truhlar DG (1985) J Chem Phys 82:2418–2427
Gutowski M, Chalasinski G (1993) J Chem Phys 98:4728–4738
Acknowledgments
This study was supported financially by the Research Centre of Ondokuz Mayis University (Project No: F-476).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Tanak, H., Ağar, A. & Yavuz, M. Experimental and quantum chemical calculational studies on 2-[(4-Fluorophenylimino)methyl]-3,5-dimethoxyphenol. J Mol Model 16, 577–587 (2010). https://doi.org/10.1007/s00894-009-0574-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00894-009-0574-2