Crystal structures and molecular modelling of 1,8 chalcogenide-substituted naphthalenes

SM Aucott; HL Milton; SD Robertson; Alexandra Martha Zoya Slawin; John Derek Woollins

doi:10.1002/hc.20055

Crystal structures and molecular modelling of 1,8 chalcogenide-substituted naphthalenes

SM Aucott, HL Milton, SD Robertson, Alexandra Martha Zoya Slawin, John Derek Woollins

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

Abstract

The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. Index Entry:

[GRAPHICS]

The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. (C) 2004 Wiley Periodicals, Inc.

Original language	English
Pages (from-to)	530-542
Number of pages	13
Journal	Heteroatom Chemistry
Volume	15
Issue number	7
DOIs	https://doi.org/10.1002/hc.20055
Publication status	Published - Jan 2004

Keywords

PROTON SPONGE
1,8-BIS(DIPHENYLPHOSPHINO)NAPHTHALENE
BIS(ETHYLENEDITHIO)TETRATHIAFULVALENE
DERIVATIVES
SYSTEMS
ANALOG
SALTS

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title = "Crystal structures and molecular modelling of 1,8 chalcogenide-substituted naphthalenes",

abstract = "The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. Index Entry:[GRAPHICS]The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. (C) 2004 Wiley Periodicals, Inc.",

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author = "SM Aucott and HL Milton and SD Robertson and Slawin, {Alexandra Martha Zoya} and Woollins, {John Derek}",

year = "2004",

month = jan,

doi = "10.1002/hc.20055",

language = "English",

volume = "15",

pages = "530--542",

journal = "Heteroatom Chemistry",

issn = "1042-7163",

publisher = "Wiley-Blackwell",

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T1 - Crystal structures and molecular modelling of 1,8 chalcogenide-substituted naphthalenes

AU - Aucott, SM

AU - Milton, HL

AU - Robertson, SD

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, John Derek

PY - 2004/1

Y1 - 2004/1

N2 - The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. Index Entry:[GRAPHICS]The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. (C) 2004 Wiley Periodicals, Inc.

AB - The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. Index Entry:[GRAPHICS]The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. (C) 2004 Wiley Periodicals, Inc.

KW - PROTON SPONGE

KW - 1,8-BIS(DIPHENYLPHOSPHINO)NAPHTHALENE

KW - BIS(ETHYLENEDITHIO)TETRATHIAFULVALENE

KW - DERIVATIVES

KW - SYSTEMS

KW - ANALOG

KW - SALTS

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DO - 10.1002/hc.20055

M3 - Article

SN - 1042-7163

VL - 15

SP - 530

EP - 542

JO - Heteroatom Chemistry

JF - Heteroatom Chemistry

IS - 7

ER -

Crystal structures and molecular modelling of 1,8 chalcogenide-substituted naphthalenes

Abstract

Keywords

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