Chemistry of mixed sulfur-, selenium-, or tellurium- and silicon-, or tin-containing heterocycles

Eric Block; Richard S. Glass; Nadine Gruhn; Jin Jin; Edward Lorance; Uzma I. Zakai; Shao Zhong Zhang

doi:10.1080/10426500801898168

Chemistry of mixed sulfur-, selenium-, or tellurium- and silicon-, or tin-containing heterocycles

Eric Block, Richard S. Glass, Nadine Gruhn, Jin Jin, Edward Lorance, Uzma I. Zakai, Shao Zhong Zhang

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

3 Scopus citations

Abstract

Lone pair ionization energies for 1,5-dichalcogenocanes containing endocyclic 3,7-R2Si groups and the parent 1,5-dichalcogenocanes, estimated from the TCNE charge-transfer wavelength maxima, are in good agreement with ionization energies directly obtained from photoelectron spectroscopy. These data indicate the occurrence of substantial intra-annular interaction between the chalcogen atoms and silyl groups, consistent with the well-known β-effect of silicon and the novel β-disilyl effect, when R (in R ₂Si) is Me₃Si.

Original language	English (US)
Pages (from-to)	856-862
Number of pages	7
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	183
Issue number	4
DOIs	https://doi.org/10.1080/10426500801898168
State	Published - Apr 2008
Externally published	Yes

Keywords

1,5-dithiocane
5-thiaselenocane
Chalcogen heterocycles
Photoelectron spectroscopy
TCNE charge transfer bands
β-disilyl effect
β-silyl effect
β-stannyl effect

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1080/10426500801898168

Cite this

@article{51f5a36a756a44b1829f624f6d493f3c,

title = "Chemistry of mixed sulfur-, selenium-, or tellurium- and silicon-, or tin-containing heterocycles",

abstract = "Lone pair ionization energies for 1,5-dichalcogenocanes containing endocyclic 3,7-R2Si groups and the parent 1,5-dichalcogenocanes, estimated from the TCNE charge-transfer wavelength maxima, are in good agreement with ionization energies directly obtained from photoelectron spectroscopy. These data indicate the occurrence of substantial intra-annular interaction between the chalcogen atoms and silyl groups, consistent with the well-known β-effect of silicon and the novel β-disilyl effect, when R (in R 2Si) is Me3Si.",

keywords = "1,5-dithiocane, 5-thiaselenocane, Chalcogen heterocycles, Photoelectron spectroscopy, TCNE charge transfer bands, β-disilyl effect, β-silyl effect, β-stannyl effect",

author = "Eric Block and Glass, {Richard S.} and Nadine Gruhn and Jin Jin and Edward Lorance and Zakai, {Uzma I.} and Zhang, {Shao Zhong}",

note = "Funding Information: The authors gratefully acknowledge support of this work by the donors of the Petroleum Research Fund administered by the American Chemical Society (EB, RSG), the National Science Foundation (CHE-9906566, CHE-0342660, CHE-0450505, CHE-0744578, EB; CHE-0201555, CHE-0455575, RSG), and NCS through a super-computing grant (EL). This work was done, in part, at the Center for Gas-Phase Electron Spectroscopy, The University of Arizona.",

year = "2008",

month = apr,

doi = "10.1080/10426500801898168",

language = "English (US)",

volume = "183",

pages = "856--862",

journal = "Phosphorus, Sulfur and Silicon and the Related Elements",

issn = "1042-6507",

publisher = "Taylor and Francis Ltd.",

number = "4",

}

TY - JOUR

T1 - Chemistry of mixed sulfur-, selenium-, or tellurium- and silicon-, or tin-containing heterocycles

AU - Block, Eric

AU - Glass, Richard S.

AU - Gruhn, Nadine

AU - Jin, Jin

AU - Lorance, Edward

AU - Zakai, Uzma I.

AU - Zhang, Shao Zhong

N1 - Funding Information: The authors gratefully acknowledge support of this work by the donors of the Petroleum Research Fund administered by the American Chemical Society (EB, RSG), the National Science Foundation (CHE-9906566, CHE-0342660, CHE-0450505, CHE-0744578, EB; CHE-0201555, CHE-0455575, RSG), and NCS through a super-computing grant (EL). This work was done, in part, at the Center for Gas-Phase Electron Spectroscopy, The University of Arizona.

PY - 2008/4

Y1 - 2008/4

N2 - Lone pair ionization energies for 1,5-dichalcogenocanes containing endocyclic 3,7-R2Si groups and the parent 1,5-dichalcogenocanes, estimated from the TCNE charge-transfer wavelength maxima, are in good agreement with ionization energies directly obtained from photoelectron spectroscopy. These data indicate the occurrence of substantial intra-annular interaction between the chalcogen atoms and silyl groups, consistent with the well-known β-effect of silicon and the novel β-disilyl effect, when R (in R 2Si) is Me3Si.

AB - Lone pair ionization energies for 1,5-dichalcogenocanes containing endocyclic 3,7-R2Si groups and the parent 1,5-dichalcogenocanes, estimated from the TCNE charge-transfer wavelength maxima, are in good agreement with ionization energies directly obtained from photoelectron spectroscopy. These data indicate the occurrence of substantial intra-annular interaction between the chalcogen atoms and silyl groups, consistent with the well-known β-effect of silicon and the novel β-disilyl effect, when R (in R 2Si) is Me3Si.

KW - 1,5-dithiocane

KW - 5-thiaselenocane

KW - Chalcogen heterocycles

KW - Photoelectron spectroscopy

KW - TCNE charge transfer bands

KW - β-disilyl effect

KW - β-silyl effect

KW - β-stannyl effect

UR - http://www.scopus.com/inward/record.url?scp=43149105791&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=43149105791&partnerID=8YFLogxK

U2 - 10.1080/10426500801898168

DO - 10.1080/10426500801898168

M3 - Article

AN - SCOPUS:43149105791

SN - 1042-6507

VL - 183

SP - 856

EP - 862

JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

IS - 4

ER -

Chemistry of mixed sulfur-, selenium-, or tellurium- and silicon-, or tin-containing heterocycles

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this