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KMID : 1059519950390070493
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Journal of the Korean Chemical Society
1995 Volume.39 No. 7 p.493 ~ p.500
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Ab Initio Studies on Proton Affinities of Substituted Oxazoles
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Lee Hyun-Mee
Lee Song-Eun
Chang Mahn-Sik
Park Byung-Kak
Lee Gab-Yong
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Abstract
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The geometry optimization of oxazole, relevant to the binding of lexitropsin that contains this ring to the base pair (G-C sequence) of minor groove of DNA, is performed with the aid of MM+ and ab initio (Hartree-Fock) calculations. The proton affinity and electronic structure are calculated at the 6-31G and 6-31G* level for the optimized geometry. The proton affinities are also studied for various substituted oxazoles with the electron-donating and -withdrawing groups to estimate the substituent effect on the proton affinities of oxazoles. It is shown that the electron-donating substituents increase the proton affinity of oxazole, while the electron-withdrawing substituents decrease it. This result can be explained with atomic charge and electron density at oxygen of substituted oxazoles.
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