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Structures and Rotational Barriers of a Diiodobinorsnoutane: Energetic Preference for Gauche Conformation.
Herres, Joseph P; Moran, Caitlin A; Forman, Mark A; Hall, James E; McCauley, John P; Pivonka, Don E; Wesolowski, Steven S.
Afiliação
  • Herres JP; Department of Chemistry, Saint Joseph's University , 5600 City Avenue, Philadelphia, Pennsylvania 19131, United States.
  • Moran CA; Department of Chemistry, Saint Joseph's University , 5600 City Avenue, Philadelphia, Pennsylvania 19131, United States.
  • Forman MA; Department of Chemistry, Saint Joseph's University , 5600 City Avenue, Philadelphia, Pennsylvania 19131, United States.
  • Hall JE; AstraZeneca Pharmaceuticals, 1800 Concord Pike, Wilmington, Delaware 19850, United States.
  • McCauley JP; AstraZeneca Pharmaceuticals, 1800 Concord Pike, Wilmington, Delaware 19850, United States.
  • Pivonka DE; AstraZeneca Pharmaceuticals, 1800 Concord Pike, Wilmington, Delaware 19850, United States.
  • Wesolowski SS; AstraZeneca Pharmaceuticals, 1800 Concord Pike, Wilmington, Delaware 19850, United States.
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.

Texto completo: 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

Texto completo: 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