Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy of Functional Groups

Sergey Z Vatsadze; Yulia D Loginova; Gabriel Dos Passos Gomes; Igor V Alabugin

doi:10.1002/chem.201603491

Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy of Functional Groups

Chemistry. 2017 Mar 8;23(14):3225-3245. doi: 10.1002/chem.201603491. Epub 2016 Nov 11.

Authors

Sergey Z Vatsadze¹, Yulia D Loginova¹, Gabriel Dos Passos Gomes², Igor V Alabugin²

Affiliations

¹ Department of Organic Chemistry, Faculty of Chemistry, Lomonosov Moscow State University, Leninsky gory, 1, 3, Moscow, Russia.
² Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, USA.

PMID: 27862399
DOI: 10.1002/chem.201603491

Abstract

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 functionalities.

Keywords: acceptors; donors; functional groups; reactive intermediates; stereoelectronic effects.

Publication types

Review