Crystal structure and rotational barrier of octakis(bromomethyl)naphthalene

Samah Simaan, Vered Marks, Hugo E. Gottlieb*, Amnon Stanger, Silvio E. Biali

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations


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° rotation of all the bromomethyl groups and reversal of the helical sense of the naphthalene core.

Original languageAmerican English
Pages (from-to)637-640
Number of pages4
JournalJournal of Organic Chemistry
Issue number2
StatePublished - 24 Jan 2003


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