For questions where the reactivity/conformation of the molecule is defined/controlled by a specific orbital arrangement/alignment (for example the unusual conformation of sugars because of the anomeric effect). This tag cannot be the only tag on a question. Tags such as [conformation] and [torganic-chemistry] must also be applied.
Definition:
Pertaining to the dependence of the properties (especially the energy) of a molecular entity in a particular electronic state (or of a transition state ) on relative nuclear geometry. The electronic ground state is usually considered, but the term can apply to excited states as well. Stereoelectronic effects arise from the different alignment of electronic orbitals in different arrangements of nuclear geometry.
The stereoelectronic effect is 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. Typical stereoelectronic effects with specific orbital overlaps generally lead to a specific molecular conformation or energy differentiation among various transition states that would lead to a particular reaction selectivity.
The stereoelectronic effect, along with the steric effect, inductive effect, mesomeric effect, etc., is one of the key theories in illustrating unusual selectivity, reactivity and stability cases in the course of organic chemistry. Its application has widely spread in organic methodology and organic synthesis. This topic is now entering biochemistry and pharmaceutical chemistry.
Further reading:
Several books have been published specifically on the topic, and may be of interested to anyone looking for information on stereoelectronic effects in organic chemistry:
- Deslongchamps, P; Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983
- Albugun, I; Stereoelectronic Effects- a bridge between structure and reactivity; Wiley: Sussex, 2016
- Yadav, V; Steric and Stereoelectronic Effects in Organic Chemistry; Springer: Singapore, 2016
