The stereoelectronic effect is defined as the effect on molecular structures, physical properties, and reactivities due to the molecules' electronic structures, in particular the interaction between atomic and/or molecular orbitals.[1] Stereoelectronic effect contains a large variety of subtopics, some of them are well known as anomeric effects and hyperconjugation.[2] Typical stereoelectronic effects with specific orbital overlaps generally lead to a specific molecular conformation, or energy differentiation among various transition states which would lead to a particular reaction selectivity.
Stereoelectronic effect generally includes a donor–acceptor interaction. The donor is usually a high-lying bonding or nonbonding orbital and the acceptor is often a low-lying antibonding orbital as shown in the scheme below. As known from the orbital–orbital interaction requirement, if this stereoelectronic effect is to be favored, the donor–acceptor orbitals must have a low energy gap and they must retain antiperiplanar geometry to allow for perfect interacting direction.
The stereoelectronic effect is defined as the effect on molecular structures, physical properties, and reactivities due to the molecules' electronic structures, in particular the interaction between atomic and/or molecular orbitals.[1] Stereoelectronic effect contains a large variety of subtopics, some of them are well known as anomeric effects and hyperconjugation.[2] Typical stereoelectronic effects with specific orbital overlaps generally lead to a specific molecular conformation, or energy differentiation among various transition states which would lead to a particular reaction selectivity.Stereoelectronic effect generally includes a donor–acceptor interaction. The donor is usually a high-lying bonding or nonbonding orbital and the acceptor is often a low-lying antibonding orbital as shown in the scheme below. As known from the orbital–orbital interaction requirement, if this stereoelectronic effect is to be favored, the donor–acceptor orbitals must have a low energy gap and they must retain antiperiplanar geometry to allow for perfect interacting direction.
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