DOI: 10.14469/hpc/7027 Metadata

Created: 2020-03-24 08:27

Last modified: 2020-04-15 07:50

Author: Henry Rzepa

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

In 2013, I created an iTunesU library of 115 mechanistic types in organic and organometallic chemistry, illustrated using video animations of the intrinsic reaction coordinate (IRC) computed using a high level quantum mechanical procedure. That course is still available here and illustrates animations of the intrinsic reaction coordinate (IRC) computed using a high level quantum mechanical procedure. It is viewable  in the  iTunesU app on an iPhone or an iPad. The realisation struck me now‡ that one of the types not described in that library was Michael 1,4-nucleophilic addition to an activated alkene, as described at  Wikipedia. So here is that addition.

Member of collection / collaboration

DOI	Description
10.14469/hpc/177	Computation data for Henry Rzepa's blog

Members

DOI	Description
10.14469/hpc/7108	Michael 1,4 addition, G =TS2 S-C formation, wB97XD/Def2-TZVPP Tolylthio G = -1014.403593 DG = 20.4
10.14469/hpc/7110	Michael 1,4 addition, G = Reactant S-C formation, wB97XD/Def2-TZVPP Tolylthio NH3 G = -994.543630
10.14469/hpc/7103	Michael 1,4 addition, G = Reactant C-C formation, wB97XD/Def2-TZVPP Tolylthio G = -1014.436207
10.14469/hpc/7106	Michael 1,4 addition, G = TS2, S-C formation, wB97XD/Def2-TZVPP Tolylthio IRC
10.14469/hpc/7113	Michael 1,4 addition, G = TS1 , wB97XD/Def2-TZVPP Tolylthio NH3 G = -994.541235 DG = 1.5
10.14469/hpc/7107	Michael 1,4 addition, G = TS2 S-C formation, wB97XD/Def2-TZVPP Tolylthio NH3 G = -994.534927 DG = 5.5
10.14469/hpc/7079	Michael 1,4 addition, G = TS2, C-C formation, wB97XD/Def2-TZVPP with cyano replacing formyl G = -494.464414 DG
10.14469/hpc/7112	Michael 1,4 addition, G = TS2 S-C formation, wB97XD/Def2-TZVPP Tolylthio NH3 IRC
10.14469/hpc/7028	Michael 1,4 addition, Reactant wB97XD/Def2-TZVPP G = -515.568171
10.14469/hpc/7029	Michael 1,4 addition, G = TS1, (PT) wB97XD/Def2-TZVPP G = -515.557495 DG = 6.7
10.14469/hpc/7030	Michael 1,4 addition TS3 (PT) wB97XD/def2tzvpp G = -515.552809
10.14469/hpc/7031	Michael 1,4 addition, G = TS2, C-C formation, wB97XD/Def2-TZVPP G = -515.542243 DG = 16.3
10.14469/hpc/7020	Michael 1,4 addition TS2, IRC.
10.14469/hpc/7036	Michael 1,4 addition Zwitterionic intermediate Int1 wB97XD/Def2-TZVPP after initial PT G = -515.580485
10.14469/hpc/7034	Michael 1,4 addition Final product wB97XD/Def2-TZVPP after TS3 G = -515.589136
10.14469/hpc/7033	Michael 1,4 addition Enol product Int2 wB97XD/Def2-TZVPP after C-C bond formation G = -515.582006
10.14469/hpc/7035	Michael 1,4 addition Int3 before final PT G = -515.582051
10.14469/hpc/7064	Michael 1,4 addition, Reactant wB97XD/Def2-TZVPP with one formyl group replaced by nitro G = -606.769958
10.14469/hpc/7043	Michael 1,4 addition, G = TS2, C-C formation, wB97XD/Def2-TZVPP with nitro replacing formyl G = -606.751701
10.14469/hpc/7039	Michael 1,4 addition, G = TS2, C-C formation, wB97XD/Def2-TZVPP with methoxy replacing formyl G = -516.691914
10.14469/hpc/7040	Michael 1,4 addition, G = TS2, C-C formation, wB97XD/Def2-TZVPP with one formyl group removed G = -402.192661 IRC
10.14469/hpc/7038	Michael 1,4 addition, Reactant wB97XD/Def2-TZVPP with one formyl group removed G = -402.249779
10.14469/hpc/7037	Michael 1,4 addition, G = TS2, C-C formation, wB97XD/Def2-TZVPP with one formyl group removed G = -402.192661
10.14469/hpc/7076	Michael 1,4 addition, Reactant wB97XD/Def2-TZVPP with one formyl group replaced by methoxy G = -516.742828
10.14469/hpc/7078	Michael 1,4 addition, TS2 wB97XD/Def2-TZVPP with one formyl group replaced by nitro IRC
10.14469/hpc/7077	Michael 1,4 addition, Reactant wB97XD/Def2-TZVPP with one formyl group replaced by cyano G = -494.491432
10.14469/hpc/7080	Michael 1,4 addition, G = TS2, C-C formation, wB97XD/Def2-TZVPP with methoxy replacing formyl G = -516.691914 IRC

Associated DOIs

Current dataset ...	DOI	Description
isReferencedBy	10.14469/hpc/7032	Associated blog post

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