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KMID : 1059519980420040391
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Journal of the Korean Chemical Society
1998 Volume.42 No. 4 p.391 ~ p.397
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Ab Initio Studies on Proton Affinities of Substituted Furans
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Lee Gab-Yong
Lee Hyun-Mee
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Abstract
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The geometry of furan, relevant to the binding of bis-furan lexitropsin that contains this ring to the base pair of minor groove of DNA, is optimized by semiempirical (MNDO) and ab initio (Hartree-Fock) methods. The proton affinity and electronic structure are evaluated at the 6-31G and 6-31G* level of theory for the optimized geometry. The proton affinities are also studied for various substituted furans with the electrondonating and -withdrawing groups to estimate the substituent effect on the proton affinity of furans. It has been found that the electron-donating substituents increase the proton affinity of furan, whereas the electron-withdrawing substituents decrease it. This result can be explained with atomic charge and electron density at oxygen of substituted furans.
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