title: Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy of Functional Groups.
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.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, Lomonosov Moscow State University, Leninsky gory, 1, 3, Moscow, Russia.
authors.forename: Sergey Z
authors.identifier: http://orcid.org/0000-0001-7884-8579
authors.initials: SZ
authors.lastname: Vatsadze
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, Lomonosov Moscow State University, Leninsky gory, 1, 3, Moscow, Russia.
authors.forename: Yulia D
authors.initials: YD
authors.lastname: Loginova
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, USA.
authors.forename: Gabriel
authors.identifier: http://orcid.org/0000-0002-8235-5969
authors.initials: G
authors.lastname: Dos Passos Gomes
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, USA.
authors.forename: Igor V
authors.identifier: http://orcid.org/0000-0001-9289-3819
authors.initials: IV
authors.lastname: Alabugin
keywords: acceptors; donors; functional groups; reactive intermediates; stereoelectronic effects