Crystal structure and rotational barrier of octakis(bromomethyl)naphthalene

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

doi:10.1021/jo026343s

Crystal structure and rotational barrier of octakis(bromomethyl)naphthalene

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

Research output: Contribution to journal › Article › peer-review

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

Original language	English
Pages (from-to)	637-640
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	68
Issue number	2
DOIs	https://doi.org/10.1021/jo026343s
State	Published - 24 Jan 2003

ASJC Scopus subject areas

Organic Chemistry

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

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T1 - Crystal structure and rotational barrier of octakis(bromomethyl)naphthalene

AU - Simaan, Samah

AU - Marks, Vered

AU - Gottlieb, Hugo E.

AU - Stanger, Amnon

AU - Biali, Silvio E.

PY - 2003/1/24

Y1 - 2003/1/24

N2 - 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.

AB - 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.

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EP - 640

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

Crystal structure and rotational barrier of octakis(bromomethyl)naphthalene

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