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目前,有机化学教科书及有关专著对羰基中氧原子是否杂化,存在着不同的意见。本文通过对羰基化合物与氧为sp~2杂化的烯醇及酚之间存在的互变异构平衡现象,以及对羰基键能、键长的分析,认为羰基中氧原子应为sp~2杂化状态。特别是羰基氧原子上孤对电子的碱性不是大于而是远远小于sp~3杂化的氧原子(H_2O、ROH、ROR),并且与sp~2杂化氧原子的碱性相当,更加证明了羰基氧原子不是非杂化的,而通常是sp~2杂化的。并澄清了认为氧原子不杂化的所谓实验根据。本文通过理论分析提出了羰基氧原子个别情况下发生sp杂化,乙烯酮的偶极矩及羰基键能数据证实了这一分析的正确性。
At present, organic chemistry textbooks and related monographs have different opinions on whether carbonyl oxygen atoms are hybridized. In this paper, through the tautomerization equilibrium between the carbonyl compounds and the enols and phenols with sp ~ 2 hybridization and the analysis of carbonyl bond energy and bond length, it is concluded that the oxygen atom in carbonyl should be sp ~ 2 Hybrid state. In particular, the basicity of the lone pair of oxygen atoms is not larger than that of the sp ~ 3 hybridized oxygen atoms (H 2 O, ROH, ROR), and is similar to that of sp ~ 2 hybrid oxygen atoms. It was demonstrated that carbonyl oxygen atoms are not nonhybridized and are usually sp ~ 2 hybridized. And clarified the so-called experimental evidence that oxygen atoms are not hybridized. In this paper, the sp hybridization, the dipole moment of ketene and the carbonyl bond energy data have been proposed by theoretical analysis to confirm the correctness of this analysis.