Structural characteristics of 2-halo-1,3,2-dithiarsenic compounds and tris-(pentafluorophenylthio)-arsen

Taimur A. Shaikh; Ronald C. Bakus; Sean Parkin; David A. Atwood

doi:10.1016/j.jorganchem.2005.12.034

Structural characteristics of 2-halo-1,3,2-dithiarsenic compounds and tris-(pentafluorophenylthio)-arsen

Taimur A. Shaikh, Ronald C. Bakus, Sean Parkin, David A. Atwood

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

34 Scopus citations

Abstract

The combination of various dithiols and AsX₃ (X = F, Cl) produces the series of cyclized halo-arsenic dithiolate compounds: 2-chloro-1,3,2-dithiarsolane [AsCl(SCH₂CH₂S)] (1), 2-iodo-1,3,2-dithiarsolane [AsI(SCH₂CH₂S)] (2), 2-chloro-1,3,2-dithiarsenane [AsCl(SCH₂CH₂CH ₂S)] (3), 2-iodo-1,3,2-dithiarsenane [AsI(SCH₂CH ₂CH₂S)] (4), 3-chloro-4H,7H-5,6-benz-1,3,2-dithiarsepine [AsCl(SCH₂)₂(C₆H₄)] (5), 1,2-bis-dithiarsolan-2-ylmercapto-ethane [As₂(SCH₂CH ₂S)₂(SCH₂CH₂S)] (6) and tris-(pentafluorophenylthio)-arsen [As(SC₆F₅)₃] (7). The geometry around As for these compounds is best described as trigonal pyramidal with varying degrees of distortion. Compound 1 crystallizes in two polymorphic forms with similar structural parameters. The compounds have been characterized by IR, ¹H, ¹⁹F, and ¹³C NMR, X-ray crystallography and GC-MS.

Original language	English
Pages (from-to)	1825-1833
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	691
Issue number	9
DOIs	https://doi.org/10.1016/j.jorganchem.2005.12.034
State	Published - Apr 15 2006

Bibliographical note

Funding Information:
This work was supported by Kentucky Science and Engineering Foundation (KSEF Grant 148-502-04-100). NMR instruments used in this research were obtained from the CRIF program of the National Science Foundation (CHE 997841) and from the Research Challenge Trust Fund of the University of Kentucky. Partial support from the Tracy Farmer Center for the Environment, University of Kentucky’s focal environmental research center, is acknowledged.

Keywords

Anomeric effect
Arsenic dithiolates
Bent's rule
Single crystal X-ray structure

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2005.12.034

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@article{5e1a0e0322334bceb42df8d0b6683e55,

title = "Structural characteristics of 2-halo-1,3,2-dithiarsenic compounds and tris-(pentafluorophenylthio)-arsen",

abstract = "The combination of various dithiols and AsX3 (X = F, Cl) produces the series of cyclized halo-arsenic dithiolate compounds: 2-chloro-1,3,2-dithiarsolane [AsCl(SCH2CH2S)] (1), 2-iodo-1,3,2-dithiarsolane [AsI(SCH2CH2S)] (2), 2-chloro-1,3,2-dithiarsenane [AsCl(SCH2CH2CH 2S)] (3), 2-iodo-1,3,2-dithiarsenane [AsI(SCH2CH 2CH2S)] (4), 3-chloro-4H,7H-5,6-benz-1,3,2-dithiarsepine [AsCl(SCH2)2(C6H4)] (5), 1,2-bis-dithiarsolan-2-ylmercapto-ethane [As2(SCH2CH 2S)2(SCH2CH2S)] (6) and tris-(pentafluorophenylthio)-arsen [As(SC6F5)3] (7). The geometry around As for these compounds is best described as trigonal pyramidal with varying degrees of distortion. Compound 1 crystallizes in two polymorphic forms with similar structural parameters. The compounds have been characterized by IR, 1H, 19F, and 13C NMR, X-ray crystallography and GC-MS.",

keywords = "Anomeric effect, Arsenic dithiolates, Bent's rule, Single crystal X-ray structure",

author = "Shaikh, {Taimur A.} and Bakus, {Ronald C.} and Sean Parkin and Atwood, {David A.}",

note = "Funding Information: This work was supported by Kentucky Science and Engineering Foundation (KSEF Grant 148-502-04-100). NMR instruments used in this research were obtained from the CRIF program of the National Science Foundation (CHE 997841) and from the Research Challenge Trust Fund of the University of Kentucky. Partial support from the Tracy Farmer Center for the Environment, University of Kentucky{\textquoteright}s focal environmental research center, is acknowledged.",

year = "2006",

month = apr,

day = "15",

doi = "10.1016/j.jorganchem.2005.12.034",

language = "English",

volume = "691",

pages = "1825--1833",

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TY - JOUR

T1 - Structural characteristics of 2-halo-1,3,2-dithiarsenic compounds and tris-(pentafluorophenylthio)-arsen

AU - Shaikh, Taimur A.

AU - Bakus, Ronald C.

AU - Parkin, Sean

AU - Atwood, David A.

N1 - Funding Information: This work was supported by Kentucky Science and Engineering Foundation (KSEF Grant 148-502-04-100). NMR instruments used in this research were obtained from the CRIF program of the National Science Foundation (CHE 997841) and from the Research Challenge Trust Fund of the University of Kentucky. Partial support from the Tracy Farmer Center for the Environment, University of Kentucky’s focal environmental research center, is acknowledged.

PY - 2006/4/15

Y1 - 2006/4/15

N2 - The combination of various dithiols and AsX3 (X = F, Cl) produces the series of cyclized halo-arsenic dithiolate compounds: 2-chloro-1,3,2-dithiarsolane [AsCl(SCH2CH2S)] (1), 2-iodo-1,3,2-dithiarsolane [AsI(SCH2CH2S)] (2), 2-chloro-1,3,2-dithiarsenane [AsCl(SCH2CH2CH 2S)] (3), 2-iodo-1,3,2-dithiarsenane [AsI(SCH2CH 2CH2S)] (4), 3-chloro-4H,7H-5,6-benz-1,3,2-dithiarsepine [AsCl(SCH2)2(C6H4)] (5), 1,2-bis-dithiarsolan-2-ylmercapto-ethane [As2(SCH2CH 2S)2(SCH2CH2S)] (6) and tris-(pentafluorophenylthio)-arsen [As(SC6F5)3] (7). The geometry around As for these compounds is best described as trigonal pyramidal with varying degrees of distortion. Compound 1 crystallizes in two polymorphic forms with similar structural parameters. The compounds have been characterized by IR, 1H, 19F, and 13C NMR, X-ray crystallography and GC-MS.

AB - The combination of various dithiols and AsX3 (X = F, Cl) produces the series of cyclized halo-arsenic dithiolate compounds: 2-chloro-1,3,2-dithiarsolane [AsCl(SCH2CH2S)] (1), 2-iodo-1,3,2-dithiarsolane [AsI(SCH2CH2S)] (2), 2-chloro-1,3,2-dithiarsenane [AsCl(SCH2CH2CH 2S)] (3), 2-iodo-1,3,2-dithiarsenane [AsI(SCH2CH 2CH2S)] (4), 3-chloro-4H,7H-5,6-benz-1,3,2-dithiarsepine [AsCl(SCH2)2(C6H4)] (5), 1,2-bis-dithiarsolan-2-ylmercapto-ethane [As2(SCH2CH 2S)2(SCH2CH2S)] (6) and tris-(pentafluorophenylthio)-arsen [As(SC6F5)3] (7). The geometry around As for these compounds is best described as trigonal pyramidal with varying degrees of distortion. Compound 1 crystallizes in two polymorphic forms with similar structural parameters. The compounds have been characterized by IR, 1H, 19F, and 13C NMR, X-ray crystallography and GC-MS.

KW - Anomeric effect

KW - Arsenic dithiolates

KW - Bent's rule

KW - Single crystal X-ray structure

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U2 - 10.1016/j.jorganchem.2005.12.034

DO - 10.1016/j.jorganchem.2005.12.034

M3 - Article

AN - SCOPUS:33645383800

SN - 0022-328X

VL - 691

SP - 1825

EP - 1833

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 9

ER -

Structural characteristics of 2-halo-1,3,2-dithiarsenic compounds and tris-(pentafluorophenylthio)-arsen

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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