Structures and Rotational Barriers of a Diiodobinorsnoutane: Energetic Preference for Gauche Conformation.
J Org Chem
; 81(15): 6862-6, 2016 08 05.
Article
em En
| MEDLINE
| ID: mdl-27391283
The diiodobinorsnoutane, bi(5-iodopentacyclo[4.3.0.0(2,4).0(3,8).0(5,7)]non-4-yl) (5), exists in a sterically hindered gauche conformation rather than an anti or an averaged (freely rotating) C2v structure. Density functional theory (DFT) predictions place the gauche conformation 11 kcal/mol more stable than the anti conformation with a barrier of 17 kcal/mol connecting the minima. These are consistent with variable-temperature NMR (17.1 ± 0.8 kcal/mol) estimates and X-ray analysis. Predictions of the torsional profiles of the yet-unsynthesized bromo-, chloro-, and fluoro- analogues show a progressive lowering of the barriers.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Tipo de estudo:
Prognostic_studies
Aspecto:
Patient_preference
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2016
Tipo de documento:
Article