Characterization of 3 fluoro-4-formylphenylboronic acid molecule with Density Functional Teory

Yıl 2018, , 1886 - 1892, 01.12.2018

Emine Babur Şaş , Mustafa Kurt

https://doi.org/10.16984/saufenbilder.423358

Öz

The geometric structure of
3-fluoro-4-fomylphenylboronic acid (3-4FPBA) molecule were investigated with
DFT/B3LYP/6-311++G(d,p) basis set. Specra of the title molecule were observed
by FT-IR and FT-Raman spectra. Theoretical wavenumber were calculated also the
same metot and compared experimental wavenumber (FT-IR and FT-Raman) which were
in a good agreement with observed ones. Furthermore, electronic structure
properties of in the title molecule such as HOMO-LUMO, Molecular Electrostatic
Potantial (MEP) and Mulliken charges were investigated by TD-DFT method.

Anahtar Kelimeler

3-fluoro-4-fomylphenylboronic acid, DFT, homo-lumo

Kaynakça

• [1] E. Frankland, B.F. Duppa, Justus Liebigs Annalen der Chem 115 (3) (1860) 319–322.[2] N.A. Petasis, Aust. J. Chem. 60 (2007) 795–798.[3] J.N. Cambre, B.S. Sumerlin, Polymer 52 (2011) 4631–4643.[4] M.R. Stabile, W.G. Lai, G. DeSantis, M. Gold, J.B. Jones, Bioorg. Med. Chem. Lett. 21 (1996) 2501–2506.[5] P.R. Westmark, B.D. Smith, J. Pharm. Sci. 85 (1996) 266–269.[6] X. Chen, G. Liang, D. Whitmire, J.P. Bowen, J. Phys. Org. Chem. 11 (1988),378-386.[7] W. Tjarks, A.K.M. Anisuzzaman, L. Liu, S.H. Soloway, R.F. Barth, D.J. Perkins, D.M. Adams, J. Med. Chem. 35 (1992). 16228-11633.[8] Y. Yamamoto, Pure Appl. Chem. 63 (1991) 423–426.[9] F. Alam, A.H. Soloway, R.F. Barth, N. Mafune, D.M. Adam, W.H. Knoth, J. Med. Chem. 32 (1989) 2326–2330.[10] Meud, A., Erbes, M., Forstinker, K., US Patent No. 2002/0 161, p. 230, 2002. [11] Freeman, A., Segal, R., Dror, Y., US Patent No. 7.825.104, B2, 2010. [12] Thornfeldt C. R., , Elias, P. M., Feingold, K. R., Holleran, W. M., US Patent No. 6,190,894, B1, 2001. [13] Weston, S., Shoichet, B., US Patent No. 6,075,014, A, 2000. [14] Shoichet, B., Weston, S., US Patent No. 6,184,363, B1, 2001.[15] Faniran, J. A., Shurvell, H. F., Infrared spectra of phenylboronic acid (normal and deuterated) and diphenyl phenylboronate, Can. J. Chem., 46, 12, pp 2089-2095, 1968. [16] Rettig, S. J., Trotter, J., Can. J. Chem., 55, 3071–3075, 1977.[17] M. J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J. R. Cross, J.B. Cheeseman, Gaussian 09, Revision A. 1 edn, Gaussian. Inc., Wallingford, CT, 2009.[18] P. Hohenberg, W. Kohn, “Inhomogeneous Electron Gas”, Physical Review, vol. 136, pp. B864, 1964.[19] A.D. Becke, “Density‐functional thermochemistry. III. The role of exact exchange”, Journal of Chemical Physics, vol. 98, pp. 5648, 1993. [20]Y.M. Wu, C.C. Dong, S. Liu, H.-J. Zhu, Y.-Z. Wu, Acta Cryst. E 62 (2006) o4236–o4237.[21] 3 floro[22] Sundaraganesan, N., Ilakiamani, S., Salem, H., Wojciechowski, P.M., Michalska, D., Spectrochim. Acta A 61, 2995–3001, 2005.[23] Faniran, J. A., Shurvell, H. F., Infrared spectra of phenylboronic acid (normal and deuterated) and diphenyl phenylboronate, Can. J. Chem., 46, 12, pp 2089-2095, 1968.[24] Erdogdu, Y., Güllüoğlu, M. T., Kurt, M., J. Raman Spectrosc. 40, 1615–1623, 2009.[25] Karabacak, M., Kose, E., Atac, A., Cipiloglu, M. A., Kurt, M., Spectrochim. Acta Part A 97, 892–908, 2012.[26] Eaton, V. J., Steele, D., J. Mol. Spectrosc. ,48, 446–458, 1973. [27] Pearce, R.A.R., Steele, D., Radcliffe, K.J., J. Mol. Struct. 15, 409–414, 1973. [28] Narasimham, N. A., El-Saban, M. Z., Rud-Nielson, J., J. Chem. Phys. 24, 420–433, 1956.[29] Silverstein, M., Basseler, G. C., Morill, C., Spectrometric Identification of Organic Compounds, Wiley: New York, 2001.[30] Kurt, M., Sertbakan, T. R., Özduran, M., Karabacak, M., J. Mol. Struct., 921, 178–187, 2009. [31] Ayyappan, S., Sundaraganesan, N., Kurt, M., Sertbakan, T.R., Özduran, M., J. Raman Spectrosc. 41, 1379–1387, 2010. [32] Kurt, M., J. Mol. Struct. 874, 159–169, 2000[33] M. Arivazhagan, D. Anitha Rexalin, “FT-IR, FT-Raman, NMR studies and ab initio-HF, DFT-B3LYP vibrational analysis of 4-chloro-2-fluoroaniline”, Spectrochimica Acta A, vol. 96, pp. 668–676, 2012.[34] Pearson, R., Absolute electronegativity and hardness: applications to organic chemistry, J. Org.Chem., 54, 1423-1430, 1989.[35] Gruber, C., Buss, V., Quantum-mechanically calculated properties for the development of quantitative structure-activity relationships (QSAR’S), pKA-values of phenols and aromatic and aliphatic carboxylic acids, Chemosphere, 19, 1595–1609, 1989. [36] Karelson, M., Lobanov, V.S., Quantum-chemical descriptors in QSAR/QSPR studies. Chemical Reviews, 96, 1027-1043, 1996.[37] Hohenberg, P., Kohn, W., Inhomogeneous Electron Gas, Physics Review, 136 (3B), 864, 1964.