TY - JOUR
T1 - Stereoelectronic effect of curved aromatic structures
T2 - Favoring the unexpected endo conformation of benzylic-substituted sumanene
AU - Higashibayashi, Shuhei
AU - Onogi, Satoru
AU - Srivastava, Hemant Kumar
AU - Sastry, G. Narahari
AU - Wu, Yao Ting
AU - Sakurai, Hidehiro
PY - 2013/7/8
Y1 - 2013/7/8
N2 - Throwing a curve: The first example of a through-bond stereoelectronic effect for curved aromatic compounds is described for buckybowls, that is, benzylic-substituted sumanenes. Methyl- and hydroxysumanene favor the endo-R conformer because of a difference in the strength, between the conformers, of the hyperconjugation of the benzylic C-H bond with the bowl.
AB - Throwing a curve: The first example of a through-bond stereoelectronic effect for curved aromatic compounds is described for buckybowls, that is, benzylic-substituted sumanenes. Methyl- and hydroxysumanene favor the endo-R conformer because of a difference in the strength, between the conformers, of the hyperconjugation of the benzylic C-H bond with the bowl.
KW - conformation analysis
KW - density functional calculations
KW - hyperconjugation
KW - through-bond interactions
KW - through-space interactions
UR - http://www.scopus.com/inward/record.url?scp=84880176212&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84880176212&partnerID=8YFLogxK
U2 - 10.1002/anie.201303134
DO - 10.1002/anie.201303134
M3 - Article
C2 - 23754738
AN - SCOPUS:84880176212
VL - 52
SP - 7314
EP - 7316
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 28
ER -