TY - JOUR
T1 - Understanding the diels-alder reactivity of superelectrophilic nitrobenzofuroxans and related 10π-heteroaromatics through DFT-based electrophilicity
AU - Lakhdar, Sami
AU - Berionni, Guillaume
AU - Goumont, Régis
AU - Terrier, Francois
PY - 2011/2
Y1 - 2011/2
N2 - A close relationship between the superelectrophilic reactivity of a large set of nitrobenzofuroxans and related 10π-heteroaromatics (nitrobenzofurazans, nitrobenzotriazoles, nitrotetrazolopyridines..) and the high propensity of these compounds to contribute to a variety of Diels-Alder processes has been experimentally established. This relationship suggests that most of the corresponding cycloadditions must be strongly polar processes. In this paper, it is shown that this important mechanistic outcome is fully supported by an analysis of the reactions on the basis of the reactivity descriptors defined by Parr within the DFT theory, namely the global electrophilicity parameter ω (and the related δNmax parameter) and the local electrophilicity parameter (ωk).
AB - A close relationship between the superelectrophilic reactivity of a large set of nitrobenzofuroxans and related 10π-heteroaromatics (nitrobenzofurazans, nitrobenzotriazoles, nitrotetrazolopyridines..) and the high propensity of these compounds to contribute to a variety of Diels-Alder processes has been experimentally established. This relationship suggests that most of the corresponding cycloadditions must be strongly polar processes. In this paper, it is shown that this important mechanistic outcome is fully supported by an analysis of the reactions on the basis of the reactivity descriptors defined by Parr within the DFT theory, namely the global electrophilicity parameter ω (and the related δNmax parameter) and the local electrophilicity parameter (ωk).
KW - DFT electrophilicity descriptors
KW - Electrophilicity scales
KW - Polar Diels-Alder cycloadditions
KW - Superelectrophilic heteroaromatics
UR - http://www.scopus.com/inward/record.url?scp=79952350512&partnerID=8YFLogxK
U2 - 10.2174/157017811794697412
DO - 10.2174/157017811794697412
M3 - Article
AN - SCOPUS:79952350512
SN - 1570-1786
VL - 8
SP - 108
EP - 118
JO - Letters in Organic Chemistry
JF - Letters in Organic Chemistry
IS - 2
ER -