Stereoelectronic Chameleons: The Donor–Acceptor Dichotomy of Functional Groups

• Published in: Chemistry : a European journal Vol. 23; no. 14; pp. 3225 - 3245
• Main Authors: Vatsadze, Sergey Z., Loginova, Yulia D., dos Passos Gomes, Gabriel, Alabugin, Igor V.
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 08.03.2017
• Subjects: acceptors; Anisotropy; Chemistry; Dichotomies; donors; Functional groups; Orientation; reactive intermediates; stereoelectronic effects; donors; functional groups; stereoelectronic effects; reactive intermediates; acceptors

Stereoelectronic factors account for the apparent reversal of donor–acceptor properties of a variety of functional groups by a simple change of their orientation in space. The new reactivity patterns that arise from spatial anisotropy are associated with chameleonic behavior of common organic functi...