Synthesis and Structural Characterization of Substituted 2-Phenacylbenzoxazoles
Skotnicka, A., Kolehmainen, E., Czelen, P., Valkonen, A., & Gawinecki, R. (2013). Synthesis and Structural Characterization of Substituted 2-Phenacylbenzoxazoles. International Journal of Moleclular Sciences, 14(3), 4444-4460. https://doi.org/10.3390/ijms14034444
Julkaistu sarjassa
International Journal of Moleclular SciencesTekijät
Päivämäärä
2013Tekijänoikeudet
© the Authors, 2013. This is an open access article distributed under the Creative Commons Attribution License (CC BY).
1
H and 13C NMR spectra of eleven 2-phenacylbenzoxazoles (ketimine form) show
that their CDCl3-solutions contains also (Z)-2-(benzo[d]oxazol-2-yl)-1-phenylethenols
(enolimine form). Intramolecular hydrogen bonding in the latter tautomer was found to be
significantly weaker than that one in respective (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines.
Integrals of the 1
H NMR signals were used to evaluate the molar ratio of the tautomers.
Strong electron-donating substituents were found to stabilize the ketimine tautomer. pKT
(negative logarithm of the equilibrium constant, KT = [ketimine]/[enolimine]) was found to
be linearly dependent on the Hammett substituent constant σ. The results of the MP2 ab
initio calculations reveal enolimine including an intramolecular OH…N hydrogen bond to
be the most stable form both with electron-donor and electron-acceptor substituents. The
stability of ketimines is an intermediate of those found for enolimines and enaminones i.e.,
(E)-2-(benzo[d]oxazol-2(3H)-ylidene)-1-phenylethanones. 13C CPMAS NMR spectral data
reveal that in the crystalline state the ketimine tautomer is predominant in p-NMe2
substituted congener. On the other hand, enolimine forms were detected there when the
substituent has less electron-donating character or when it is an electron-acceptor
by character.
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1422-0067Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/22357798
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