Theoretical studies on the gas-phase pyrolysis of 2-trimethylsilylethanol

Yong Wu; Lu Jin; Ying Xue; Chan Kyung Kim

doi:10.1016/j.theochem.2009.11.017

Theoretical studies on the gas-phase pyrolysis of 2-trimethylsilylethanol

Yong Wu
, Lu Jin
, Ying Xue
, Chan Kyung Kim

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

Abstract

In this work, pyrolysis of 2-trimethylsilylethanol was investigated via two possible decomposition pathways. Path A was the elimination of β-SiMe₃ towards trimethylsilanol and ethylene, while path B was the elimination of β-H towards water and trimethylsilylethylene. Our results indicated that path A was favored. The driving force for the thermal decomposition was analyzed in detail using bond dissociation energies, orbital interactions, and ring strains. We also found that, compared to MP2 and experimental results, both BB1K and MPWB1K DFT methods were good to describe the energy barriers.

Original language	English
Pages (from-to)	127-132
Number of pages	6
Journal	Journal of Molecular Structure: THEOCHEM
Volume	941
Issue number	1-3
DOIs	https://doi.org/10.1016/j.theochem.2009.11.017
State	Published - 15 Feb 2010
Externally published	Yes

Keywords

1,3-Silyl transfer
2-Trimethylsilylethanol
Hypervalent transition state
Pyrolysis
β-Elimination

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10.1016/j.theochem.2009.11.017

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title = "Theoretical studies on the gas-phase pyrolysis of 2-trimethylsilylethanol",

abstract = "In this work, pyrolysis of 2-trimethylsilylethanol was investigated via two possible decomposition pathways. Path A was the elimination of β-SiMe3 towards trimethylsilanol and ethylene, while path B was the elimination of β-H towards water and trimethylsilylethylene. Our results indicated that path A was favored. The driving force for the thermal decomposition was analyzed in detail using bond dissociation energies, orbital interactions, and ring strains. We also found that, compared to MP2 and experimental results, both BB1K and MPWB1K DFT methods were good to describe the energy barriers.",

keywords = "1,3-Silyl transfer, 2-Trimethylsilylethanol, Hypervalent transition state, Pyrolysis, β-Elimination",

author = "Yong Wu and Lu Jin and Ying Xue and Kim, \{Chan Kyung\}",

year = "2010",

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doi = "10.1016/j.theochem.2009.11.017",

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volume = "941",

pages = "127--132",

journal = "Journal of Molecular Structure: THEOCHEM",

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TY - JOUR

T1 - Theoretical studies on the gas-phase pyrolysis of 2-trimethylsilylethanol

AU - Wu, Yong

AU - Jin, Lu

AU - Xue, Ying

AU - Kim, Chan Kyung

PY - 2010/2/15

Y1 - 2010/2/15

N2 - In this work, pyrolysis of 2-trimethylsilylethanol was investigated via two possible decomposition pathways. Path A was the elimination of β-SiMe3 towards trimethylsilanol and ethylene, while path B was the elimination of β-H towards water and trimethylsilylethylene. Our results indicated that path A was favored. The driving force for the thermal decomposition was analyzed in detail using bond dissociation energies, orbital interactions, and ring strains. We also found that, compared to MP2 and experimental results, both BB1K and MPWB1K DFT methods were good to describe the energy barriers.

AB - In this work, pyrolysis of 2-trimethylsilylethanol was investigated via two possible decomposition pathways. Path A was the elimination of β-SiMe3 towards trimethylsilanol and ethylene, while path B was the elimination of β-H towards water and trimethylsilylethylene. Our results indicated that path A was favored. The driving force for the thermal decomposition was analyzed in detail using bond dissociation energies, orbital interactions, and ring strains. We also found that, compared to MP2 and experimental results, both BB1K and MPWB1K DFT methods were good to describe the energy barriers.

KW - 1,3-Silyl transfer

KW - 2-Trimethylsilylethanol

KW - Hypervalent transition state

KW - Pyrolysis

KW - β-Elimination

UR - https://www.scopus.com/pages/publications/73749088001

U2 - 10.1016/j.theochem.2009.11.017

DO - 10.1016/j.theochem.2009.11.017

M3 - 文章

AN - SCOPUS:73749088001

SN - 0166-1280

VL - 941

SP - 127

EP - 132

JO - Journal of Molecular Structure: THEOCHEM

JF - Journal of Molecular Structure: THEOCHEM

IS - 1-3

ER -

Theoretical studies on the gas-phase pyrolysis of 2-trimethylsilylethanol

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Keywords

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