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Experimental Diels–Alder Reactivities of Cycloalkenones and Cyclic Dienes Explained through Transition‐State Distortion Energies
Author(s) -
Paton Robert S.,
Kim Seonah,
Ross Audrey G.,
Danishefsky Samuel J.,
Houk K. N.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201103998
Subject(s) - distortion (music) , diene , quantum chemical , constant (computer programming) , computational chemistry , state (computer science) , diels–alder reaction , content (measure theory) , chemistry , physics , organic chemistry , mathematics , computer science , molecule , catalysis , optoelectronics , algorithm , amplifier , mathematical analysis , natural rubber , cmos , programming language
Quantum chemical calculations are used to investigate the experimentally measured reactivities of cyclic dienes and cycloalkenones in the Diels–Alder reaction. The interaction energies (red) are nearly constant; differences arise in changes in distortion energies of both dienophile (blue) and diene (green; see picture, E a =activation energy; values in kcal mol −1 ).