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

Department of Chemistry

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

7 Scopus citations

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

Access to Document

10.1021/jo026343s

Cite this

@article{416ab67b42d04f9ca815ef3fb4b9d15c,

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.",

author = "Samah Simaan and Vered Marks and Gottlieb, {Hugo E.} and Amnon Stanger and Biali, {Silvio E.}",

year = "2003",

month = jan,

day = "24",

doi = "10.1021/jo026343s",

language = "אנגלית",

volume = "68",

pages = "637--640",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0346034634&partnerID=8YFLogxK

U2 - 10.1021/jo026343s

DO - 10.1021/jo026343s

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

C2 - 12530901

AN - SCOPUS:0346034634

SN - 0022-3263

VL - 68

SP - 637

EP - 640

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

Crystal structure and rotational barrier of octakis(bromomethyl)naphthalene

Abstract

Access to Document

Other files and links

Fingerprint

Cite this