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12 not so angry men: Hexaphenylethane is unstable, a phenomenon traditionally attributed to steric repulsion between the six phenyl rings. However, adding 12 bulky tert-butyl groups, one to each of the 12 meta positions, gives a stabile ethane derivative (see space-filling model and potential energy curve for the dissociation of the central C-C bond). This unexpected stabilization is shown to result from attractive dispersion interactions between the substituents.


Rsel, S.; Quanz, H.; Logemann, C.; Becker, J.; Mossou, E.; Caadillas-Delgado, L.; Caldeweyher, E.; Grimme, S.; Schreiner, P. R.,  J. Am. Chem. Soc. 2017, 139, 74287431Contributed by Steven BacharachReposted from Computational Organic Chemistry with permissionFollowing...
Following on previous work (see these posts on ladderane and hexaphenylethane), Schreiner, Grimme and co-workers have examined the structure of the all-meta tri(di-t-butylphenyl)methane dimer 12.1 In the study of hexaphenylethane,2 Schreiner and Grimme note...
Fokin, A. A.; Chernish, L. V.; Gunchenko, P. A.; Tikhonchuk, E. Y.; Hausmann, H.; Serafin, M.; Dahl, J. E. P.; Carlson, R. M. K.; Schreiner, P. R. J. Am. Chem. Soc., 2012, 134, 13641 (Paywall)Contributed by Steven Bachrach.Reposted from Computational Organic...
Schreiner has expanded on his previous paper1 regarding alkanes with very long C-C bonds, which I commented upon in this post. He and his colleagues report2 now a series of additional diamond-like and adamantane-like sterically congested alkanes that are stable...
S. Grimme and P. R. Schreiner,Angew. Chem. Int. Ed. 2011, 50, 12639Inthe special issue 90 Years of Chemical Bonding1 I expressed theopinion2 that despite of the historians characterization ofchemistry as a science without territory, the chemical bond has been...