Tautomeric design of ortho-hydroxyheterocyclic Schiff bases

作者: Agnieszka Kwocz , Andrzej Kochel , Dorota Chudoba , Aleksander Filarowski

DOI: 10.1016/J.MOLSTRUC.2014.09.073

关键词:

摘要: Abstract The article reports on the synthesis and crystallographic theoretical studies various heterocyclic derivatives of ortho-hydroxy Schiff bases. prevailing one two (enolimine – OH ketoamine NH) tautomeric forms has been stated in studied compounds depending substitutes formation, nitrogen carbon atoms imine group. A specific situation shown (1E)-1-(5-chloro-2-hydroxy-3-nitrophenyl)ethanone oxime compound. potentials proton transfer hydrogen bridges these have found out. Grounded obtained potential curves influence protonation pyridoxal derivative bases analysed. most efficient method impact (by means substitutes) intramolecular equilibrium presented.

参考文章(32)
George A. Jeffrey, An Introduction to Hydrogen Bonding ,(1997)
D. Hadži, Theoretical treatments of hydrogen bonding John Wiley & Sons. ,(1997)
R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions Journal of Chemical Physics. ,vol. 72, pp. 650- 654 ,(1980) , 10.1063/1.438955
Katarzyna Filipczak, Jerzy Karolczak, Marcin Ziółek, Temperature influence on deactivation paths and tautomeric equilibrium of some photochromic Schiff bases studied by time-resolved and stationary spectroscopy Photochemical and Photobiological Sciences. ,vol. 8, pp. 1603- 1610 ,(2009) , 10.1039/B9PP00040B
Aleksander Filarowski, Aleksander Koll, Tadeusz Glowiak, Eugeniusz Majewski, Teresa Dziembowska, Proton transfer reaction in N-methyl-2-hydroxy-Schiff bases International Autumn Bunsen Discussion Meeting 1997 on Hydrogen Transfer: Theory and Experiment. ,vol. 102, pp. 393- 402 ,(1998) , 10.1002/BBPC.19981020317
A. D. McLean, G. S. Chandler, Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18 Journal of Chemical Physics. ,vol. 72, pp. 5639- 5648 ,(1980) , 10.1063/1.438980
Aleksander Filarowski, Aleksander Koll, Tadeusz Głowiak, Proton transfer equilibrium in the intramolecular hydrogen bridge in sterically hindered Schiff bases Journal of Molecular Structure. ,vol. 615, pp. 97- 108 ,(2002) , 10.1016/S0022-2860(02)00211-9
Joanna Grzegorzek, Zofia Mielke, Photochemistry of Salicylaldoxime in Solid Argon: An Experimental and Theoretical Study European Journal of Organic Chemistry. ,vol. 2010, pp. 5301- 5309 ,(2010) , 10.1002/EJOC.201000348
Sławomir Szymański, Piotr Paluch, Daniel T. Gryko, Agnieszka Nowak-Król, Wojciech Bocian, Jerzy Sitkowski, Beata Koszarna, Justyna Śniechowska, Marek J. Potrzebowski, Lech Kozerski, Insights into the tautomerism in meso-substituted corroles: a variable-temperature 1H, 13C, 15N, and 19F NMR spectroscopy study. Chemistry: A European Journal. ,vol. 20, pp. 1720- 1730 ,(2014) , 10.1002/CHEM.201303406
Salem Abood Hameed, Saaban K. Alrouby, Rifaat Hilal, Design of molecular switching and signaling based on proton transfer in 2-hydroxy Schiff bases: a computational study Journal of Molecular Modeling. ,vol. 19, pp. 559- 569 ,(2013) , 10.1007/S00894-012-1578-X