title: Crystal structure and rotational barrier of octakis(bromomethyl)naphthalene.
abstract: Octakis(bromomethyl)naphthalene (4) adopts in the crystal a chiral conformation with a helical central naphthalene core and the bromomethyl groups disposed in an alternate up-down "in" arrangement. According to MM3 calculations, this conformation is less stable than the corresponding all alternated "out" form, while B3LYP/LANL2DZ calculations suggest the opposite stability order. The topomerization barrier (16.0 kcal mol(-1)) is ascribed to an enantiomerization process requiring 180 degrees rotation of all the bromomethyl groups and reversal of the helical sense of the naphthalene core.
authors.affiliation: Department of Organic Chemistry, The Hebrew University of Jerusalem, Israel.
authors.forename: Samah
authors.initials: S
authors.lastname: Simaan
authors.forename: Vered
authors.initials: V
authors.lastname: Marks
authors.forename: Hugo E
authors.initials: HE
authors.lastname: Gottlieb
authors.forename: Amnon
authors.initials: A
authors.lastname: Stanger
authors.forename: Silvio E
authors.initials: SE
authors.lastname: Biali