|
A Solid State Study of Keto-enol Tautomerismin Three Naphthaledene Schiff Bases
Gregory K.
Pierens A C,
T. K.
Venkatachalam A,
Paul V.
Bernhardt B,
Mark J.
Riley B and
David C.
Reutens A
A
Centre for Advanced Imaging, The University of Queensland, Brisbane, Qld 4072, Australia.
B
School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.
C
Corresponding author. Email: g.pierens@uq.edu.au
Australian Journal of Chemistry
65(5)
552-556 http://dx.doi.org/10.1071/CH12122
Submitted: 28 February 2012 Accepted: 6 March 2012 Published:
10
May
2012
|  |
|
|
Abstract
Three naphthaledene Schiff bases were synthesized and a detailed analysis by variable temperature X-ray crystallography and solid state electronic spectra was undertaken to assess the tautomeric composition. The crystal structures showed no significant changes despite the compounds changing colour with temperature. Solid state UV spectra were acquired at low temperature and showed that the major absorption band broadened as the temperature was increased. In one compound absorptions were observed that increased in intensity as the temperature increased. For these compounds, the major contribution to the colour change is the broadening of the absorption band as a function of temperature and not the change in enol-keto tautomeric composition. 
|
References
[1]
T. Hokelek, Z. Kiliç, M. Isiklan, M. Toy, J. Mol. Struct. 2000, 523, 61.
| CrossRef | CAS | 
[2]
E. Matito, M. Duran, M. Solà, J. Chem. Phys. 2005, 122, 014109.
| CrossRef |
[3]
P. Nagy, R. Herzfeld, Spectrosc. Lett. 1998, 31, 221.
| CrossRef | CAS |
[4]
H. Unver, D. M. Zengin, K. G¸ven, J. Chem. Crystallogr. 2000, 30, 359.
| CrossRef | CAS |
[5]
J. W. Ledbetter, J. Phys. Chem. 1966, 70, 2245.
| CrossRef | CAS |
[6]
A. M. Asiri, K. O. Badahdah, Molecules 2007, 12, 1796.
| CrossRef | CAS |
[7]
L. Antonov, W. M. F. Fabian, D. Nedeltcheva, F. S. Kamounah, J. Chem. Soc., Perkin Trans. 2 2000, 2000, 1173.
| CrossRef |
[8]
H. Nazir, M. Yildiz, H. Yilmaz, M. Tahir, D. Ulku, J. Mol. Struct. 2000, 524, 241.
| CrossRef | CAS |
[9]
T. Venkatachalam, G. K. Pierens, P. V. Bernhardt, L. Hammond, D. C. Reutens, J. Chem. Crystallogr. 2011, 41, 944.
| CrossRef | CAS |
[10]
T. Inabe, I. Luneau, T. Mitani, Y. Maruyama, S. Takeda, Bull. Chem. Soc. Jpn. 1994, 67, 612.
| CrossRef | CAS |
[11]
W. Schilf, B. Kamieski, T. Dziembowska, J. Mol. Struct. 2002, 602, 41.
| CrossRef |
[12]
B. L. Feringa, W. F. Jager, B. De Lange, Tetrahedron 1993, 49, 8267.
| CrossRef | CAS |
[13]
E. Hadjoudis, Mol. Eng. 1995, 5, 301.
| CrossRef | CAS |
[14]
J. C. Zhuo, Magn. Reson. Chem. 1999, 37, 259.
| CrossRef | CAS |
[15]
P. Gilli, V. Bertolasi, L. Pretto, A. Lycka, G. Gilli, J. Am. Chem. Soc. 2002, 124, 13554.
| CrossRef | CAS |
[16]
V. F. Traven, I. V. Ivanov, V. S. Lebedev, B. G. Milevskii, T. A. Chibisova, N. P. Solovíeva, V. I. Polshakov, O. N. Kazheva, G. G. Alexandrov, O. A. Dyachenko, Mendeleev Commun. 2009, 19, 214.
| CrossRef | CAS |
[17]
K. Ogawa, Y. Kasahara, Y. Ohtani, J. Harada, J. Am. Chem. Soc. 1998, 120, 7107.
| CrossRef | CAS |
[18]
E. Hadjoudis, S. D. Chatziefthimiou, I. M. Mavridis, Curr. Org. Chem. 2009, 13, 269.
| CrossRef | CAS |
[19]
T. Venkatachalam, G. K. Pierens, D. Reutens, Aust. J. Chem. 2010, 63, 1272.
| CrossRef | CAS |
[20]
S. H. Alarcon, A. C. Olivieri, D. Sanz, R. M. Claramunt, J. Elguero, J. Mol. Struct. 2004, 705, 1.
| CrossRef | CAS |
[21]
A. C. Olivieri, R. B. Wilson, I. C. Paul, D. Y. Curtin, J. Am. Chem. Soc. 1989, 111, 5525.
| CrossRef | CAS |
[22]
P. V. Rao, C. P. Rao, E. K. Wegelius, K. Rissanen, J. Chem. Crystallogr. 2003, 33, 139.
| CrossRef | CAS |
[23]
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2 1987, 12, S1.
| CrossRef |
[24]
G. Sheldrick, Acta Crystallogr. A 2008, 64, 112.
| CrossRef |
[25]
L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837.
| CrossRef | CAS |
[26]
L. Farrugia, J. Appl. Cryst. 1997, 30, 565.
| CrossRef | CAS |
[27]
M. J. Riley, E. R. Krausz, A. Stanco, J. Inorg. Biochem. 2003, 96, 217.
| CrossRef |
[28]
M. A. Hitchman, M. J. Riley, Polarised Absorption Spectroscopy, Chapter 4, Inorganic Electronic Structure and Spectroscopy, Volume I: Methodology, 1999 (Eds E. I. Solomon, A. B. P. Lever) (John Wiley & Sons: New York).
|
|
 |
Subscriber Login |
 |
|
e-Alerts
Connect with us
