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- W4241001424 abstract "This chapter concentrates on “second-order” interactions - the deviations from the main Lewis structure that are needed to describe real molecules. All of these phenomena (conjugation, hyperconjugation, and σ-conjugation) correspond to delocalization, expanding the potential energy box further and allowing “parts” of the molecules to interact. The chapter focuses on the interaction of vicinal orbitals at two directly connected atoms. The stereoelectronic aspects of vicinal interactions are immediately obvious when stability and reactivity change as a function of relative arrangement of the interacting bonds in space. This chapter introduces the “main rule” of stereoelectronic interactions, i.e. the pronounced preference for antiperiplanarity of the vicinal donor and acceptor orbitals. Subsequent discussion concentrates on the intrinsic properties of common donor and acceptor orbitals that control the magnitude of stereoelectronic interactions. In particular, the roles of polarization, hybridization, and orbital energy effects are outlined and the general comparison of common donors and acceptors is provided. The chapter also introduces “chemical chameleons” - functionalities capable of stereoelectronic “conversion” from a donor to an acceptor induced by a conformational change. The final section discusses cooperativity of stereoelectronic effects and its relation to the antiperiplanar lone pair hypothesis (ALPH) theory." @default.
- W4241001424 created "2022-05-12" @default.
- W4241001424 date "2016-08-26" @default.
- W4241001424 modified "2023-09-23" @default.
- W4241001424 title "General Stereoelectronic Trends - Donors, Acceptors, and Chameleons" @default.
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- W4241001424 doi "https://doi.org/10.1002/9781118906378.ch5" @default.
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