This review outlines the role of hyperconjugative interactions in the structure and reactivity of organic molecules. After defining the common hyperconjugative patterns, we discuss the main factors controlling the magnitude of hyperconjugative effects, including orbital symmetry, energy gap, electronegativity, and polarizability. The danger of underestimating the contribution of hyperconjugative interactions are illustrated by a number of spectroscopic, conformational, and structural effects. The stereoelectronic nature of hyperconjugation offers useful ways for control of molecular stability and reactivity. New manifestations of hyperconjugative effects continue to be uncovered by theory and experiments.

中文翻译：

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超共轭

这篇综述概述了超共轭相互作用在有机分子的结构和反应性中的作用。在定义了常见的超共轭模式后，我们讨论了控制超共轭效应大小的主要因素，包括轨道对称性，能隙，电负性和极化率。许多光谱，构象和结构效应说明了低估高共轭相互作用贡献的危险。高共轭的立体电子性质为控制分子稳定性和反应性提供了有用的方法。理论和实验继续揭示高共轭作用的新表现。