Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Aromaticity of C20H10-xFx Corannulene: A Comparative Study by NICS and EFG Methods

Author(s): Farrokh Roya Nikmaram* and Khadijeh Kalateh

Volume 16, Issue 7, 2019

Page: [592 - 599] Pages: 8

DOI: 10.2174/1570178615666181024115442

Price: $65

Abstract

Corannulene (C20H10) and its fluorinated derivatives, C20H10-xFx (x=1-10), are investigated at the B3LYP/6-31G level of density functional theory. The degree of electron delocalization is evaluated using Nucleus Independent Chemical Shift (NICS) method, Electric Field Gradient (EFG) method and factor of Ellipticity (ε). In this study, the benzene is the scale of comparison as a more aromatic structure. The aromaticity has been evaluated at three points of structures; center of five-member ring (5-MR), center of fluorine-substituted ring (6-MR), and center of other six-member rings. This comparison shows that substitution of fluorine for four and five hydrogen atoms in the Corannulene structure, C20H10-xFx (x=4, 5), results in more aromaticity compared to the other substitutions, and C20H10 and C20H10-xFx (x=1, 3) are more antiaromatic. It seems that the EFG method is more reliable for forecasting the aromaticity of structures, than NICS method. The factor of Ellipticity and bond lengths resulted from Atom in Molecule (AIM) analysis support the EFG method.

Keywords: Aromaticity, NICS, EFG, ellipticity, corannulene, fluorine substitution.

« Previous Next »
Graphical Abstract

[1]
Neumann, W.L.; Cacheris, W.P. Fullerene compositions for magnetic resonance spectroscopy and imaging, ZUSAMMENFASSUNG. U.S. Patent 5248498 A, 2017.
[2]
Nakajima, T.; Zemva, B.; Tressaud, A. Fluorinated Fullerenes, Advanced Inorganic Fluorides Synthesis, Characterization and Applications; Elsevier Science, 2000.
[3]
Kumar, P.S.V.; Aghavendra, V.; Subramanian, V. J. Chem. Sci., 2016, 128, 1527-1536.
[4]
Becke, A.D. J. Chem. Phys., 1993, 98, 5648-5652.
[5]
Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B, 1988, 37, 785.
[6]
Peverati, R.; Truhlar, D.G. J. Chem. Phys., 2011, 135, 191102.
[7]
Frisch, M.J.; Pople, J.A.; Binkley, J.S. J. Chem. Phys., 1984, 80, 3265-3269.
[8]
Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuserial, G. Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA. 1998.
[9]
Schleyer, P.V.R.; Maerker, C.; Dransfeld, A.; Jiao, H. J. Am. Chem. Soc., 1996, 118, 6317-6318.
[10]
Choh, S.H.; Shin, H.W.; Park, W.; Kim, J.H. J. Korean Soc. Magn. Reson. Med., 2003, 7, 16.
[11]
Schleyer, P.V.R.; Manoharan, M.; Wang, Z.X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N.J.R.V.E. Org. Lett., 2001, 3, 2465-2468.
[12]
Spiegel, M.; Lipcshutz, S.; Spellman, D. Vector Analysis, 2nd Edition, McGraw Hill: USA, ISBN 978- 0071615457. 2009.
[13]
Grant, I.S.; Phillips, W.R. Electromagnetism, 2nd Edition, John Wiley & Sons, Manchester Physics, ISBN 978-0-471-92712-9. 2008.
[14]
Griffiths, D.J. Introduction to Electrodynamics, 3rd Edition, Prentice- Hall, Inc: ISBN 13-805326. 1999.
[15]
Mohajeri, A.; Shahamirian, M. J. Phys. Org. Chem., 2010, 23, 440-450.
[16]
Silva, L.C. R de Lera, A. Curr. Org. Chem., 2011, 20, 3576-3593.
[17]
D., Auria M. Lett. Org. Chem., 2014, 11, 731-735.
[18]
D., Auria M. Lett. Org. Chem., 2016, 13, 33-43.
[19]
D., Auria M. Lett. Org. Chem., 2016, 5, 330-337.
[20]
Bader, R.F.W. Atoms in Molecules: A Quantum Theory; Oxford University, Press: Oxford, U.K., 1990.
[21]
Bader, R.F.W. Hanneker, W.H.; Cade, P.E. J. Chem. Phys., 1967, 46, 3341-3363.
[22]
Bader, R.F.W. Essen, H. J. Chem. Phys., 1984, 80, 1943-1960.
[23]
Bader, R.F.W. Can. J. Chem., 1998, 76, 973-988.
[24]
Carlos Silva, L.; Olalla Nieto, F. Fernando. P.C.; Darrin, M.Y.; Angel, R.L. Chem. Eur. J., 2005, 11, 1734.
[25]
Ditchfield, R. Chem. Phys. Lett., 1972, 15, 203-206.
[26]
Monajjemi, M.; Ahmadianarog, M. J. Comput. Theor. Nanosci., 2014, 11, 1465-1471.
[27]
Buhl, M.; Wullen, C.V. Chem. Phys. Lett., 1995, 247, 63-68.
[28]
(a)Hirsch, A. Chemistry of the Fullerene; Thieme Verlag: Stuttgart, New York, 1994.
(b)Prato, M.; Suzuki, T.; Wudl, F.; Lucchini, V.; Maggini, M. J. Am. Chem. Soc., 1993, 115, 7876-7877.
[29]
Pasquarello, A.; Schluter, M.; Haddon, R.C. Science, 1992, 257, 1660-1661.
[30]
Korenaga, T.; Kobayashi, F.; Nomura, K.; Sakai, T.; Shimada, K. J. Fluor. Chem., 2013, 156, 1-4.
[31]
Najafpour, J. Comput. Theor. Chem., 2014, 1046, 1-5.
[32]
Pakiari, A.H.; Bagheri, N. J. Mol. Model., 2011, 17, 2017-2027.
[33]
Gregory, V.L.; Cases, M.; Ewels, C.P.; Taylor, R.; Geerlings, P. J. Org. Chem., 2005, 70, 1565-1579.

Rights & Permissions Print Cite
Article Metrics
37
2
© 2024 Bentham Science Publishers | Privacy Policy