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In chemistry, primarily organic and comput … In chemistry, primarily organic and computational chemistry, a stereoelectronic effect is an effect on molecular geometry, reactivity, or physical properties due to spatial relationships in the molecules' electronic structure, in particular the interaction between atomic and/or molecular orbitals. Phrased differently, stereoelectronic effects can also be defined as the geometric constraints placed on the ground and/or transition states of molecules that arise from considerations of orbital overlap. Thus, a stereoelectronic effect explains a particular molecular property or reactivity by invoking stabilizing or destabilizing interactions that depend on the relative orientations of electrons (bonding or non-bonding) in space. Stereoelectronic effects present themselves in other well-known interactions. These include important phenomena such as the anomeric effect and hyperconjugation. It is important to note that stereoelectronic effects should not be misunderstood as a simple combination of steric effects and electronic effects. Founded on a few general principles that govern how orbitals interact, the stereoelectronic effect, along with the steric effect, inductive effect, solvent effect, mesomeric effect, and aromaticity, is an important type of explanation for observed patterns of selectivity, reactivity, and stability in organic chemistry. In spite of the relatively straightforward premises, stereoelectronic effects often provide explanations for counterintuitive or surprising observations. As a result, stereoelectronic factors are now commonly considered and exploited in the development of new organic methodology and in the synthesis of complex targets. The scrutiny of stereoelectronic effects has also entered the realms of biochemistry and pharmaceutical chemistry in recent years. A stereoelectronic effect generally involves a stabilizing donor-acceptor (i.e., filled bonding-empty antibonding, 2-electron 2-orbital) interaction. The donor is usually a higher bonding or nonbonding orbital and the acceptor is often a low-lying antibonding orbital as shown in the scheme below. Whenever possible, if this stereoelectronic effect is to be favored, the donor-acceptor orbitals should have (1) a small energy gap and (2) be geometrically well disposed for interaction. In particular, this means that the shapes of the donor and acceptor orbitals (including π or σ symmetry and size of the interacting lobes) must be well-matched for interaction; an antiperiplanar orientation is especially favorable. Some authors require stereoelectronic effects to be stabilizing. However, destabilizing donor-donor (i.e., filled bonding-filled antibonding, 4-electron 2-orbital) interactions are occasionally invoked and are also sometimes referred to as stereoelectronic effects, although such effects are difficult to distinguish from generic steric repulsion.distinguish from generic steric repulsion.
, Les effets stéréoélectroniques (au pluriel, en général) regroupent les influences stériques et électroniques intervenant dans le déroulement d'une réaction chimique ou dans la conformation d'une molécule.
, 立体電子効果（りったいでんしこうか、英: stereoelectronic effect）とは、ある特定の立体配座や立体配置においてのみ働く軌道間の相互作用によって、化合物の構造や安定性や反応性に影響が及ぶことをいう。 軌道同士が相互作用するためには空間的に近接しなければならないので、化合物がある特定の立体配座や立体配置をとった時にだけ相互作用が働くことがある。するとその特定の配座や配置が安定化されたり、それらの持つ反応性が強調されることになる。
, Stereoelektronische Effekte sind räumliche … Stereoelektronische Effekte sind räumliche Orientierungen von Molekülen oder bestimmte Verläufe einer chemischen Reaktion, welche sich aus der räumlichen Anordnung von Molekülorbitalen ergeben. Die Bevorzugung dieser folgt dabei aus Donor-Akzeptor-Wechselwirkungen dieser Orbitale.Akzeptor-Wechselwirkungen dieser Orbitale.
, 立体电子效应，重要理论有机化学概念之一。立体电子效应是综合了立体效应和电子效应的结果，但不是简单的两种效应加合的结果。由于共价键具有方向性，即具有特定的空间取向，这导致了电子效应对分子不同部位的影响存在差异。这就是立体电子效应最根本的立足点。 立体电子效应可以解释很多其他效应解释不了的现象。比如二氯甲烷的惰性问题，内酯比酯活泼的问题，环醚比醚活泼的问题等等。下面举例说明立体电子效应的应用和意义。立体电子效应这个术语是E.J.Corey于60年代发明的。
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In chemistry, primarily organic and comput … In chemistry, primarily organic and computational chemistry, a stereoelectronic effect is an effect on molecular geometry, reactivity, or physical properties due to spatial relationships in the molecules' electronic structure, in particular the interaction between atomic and/or molecular orbitals. Phrased differently, stereoelectronic effects can also be defined as the geometric constraints placed on the ground and/or transition states of molecules that arise from considerations of orbital overlap. Thus, a stereoelectronic effect explains a particular molecular property or reactivity by invoking stabilizing or destabilizing interactions that depend on the relative orientations of electrons (bonding or non-bonding) in space.ectrons (bonding or non-bonding) in space.
, Stereoelektronische Effekte sind räumliche … Stereoelektronische Effekte sind räumliche Orientierungen von Molekülen oder bestimmte Verläufe einer chemischen Reaktion, welche sich aus der räumlichen Anordnung von Molekülorbitalen ergeben. Die Bevorzugung dieser folgt dabei aus Donor-Akzeptor-Wechselwirkungen dieser Orbitale.Akzeptor-Wechselwirkungen dieser Orbitale.
, 立体電子効果（りったいでんしこうか、英: stereoelectronic effect）とは、ある特定の立体配座や立体配置においてのみ働く軌道間の相互作用によって、化合物の構造や安定性や反応性に影響が及ぶことをいう。 軌道同士が相互作用するためには空間的に近接しなければならないので、化合物がある特定の立体配座や立体配置をとった時にだけ相互作用が働くことがある。するとその特定の配座や配置が安定化されたり、それらの持つ反応性が強調されることになる。
, Les effets stéréoélectroniques (au pluriel, en général) regroupent les influences stériques et électroniques intervenant dans le déroulement d'une réaction chimique ou dans la conformation d'une molécule.
, 立体电子效应，重要理论有机化学概念之一。立体电子效应是综合了立体效应和电子效应的结果，但不是简单的两种效应加合的结果。由于共价键具有方向性，即具有特定的空间取向，这导致了电子效应对分子不同部位的影响存在差异。这就是立体电子效应最根本的立足点。 立体电子效应可以解释很多其他效应解释不了的现象。比如二氯甲烷的惰性问题，内酯比酯活泼的问题，环醚比醚活泼的问题等等。下面举例说明立体电子效应的应用和意义。立体电子效应这个术语是E.J.Corey于60年代发明的。
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Stereoelektronische Effekte
, 立体电子效应
, Stereoelectronic effect
, Effet stéréoélectronique
, 立体電子効果
|
