Thermal stability of N-heterocycle-stabilized iodanes-A systematic investigation

Andreas Boelke, Yulia A. Vlasenko, Mekhman S. Yusubov, Boris J. Nachtsheim, Pavel S. Postnikov

Research output: Contribution to journalArticle

Abstract

The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl-and mesityl(aryl)-λ3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures (Tpeak) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (ΔHdec) varied from-29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high Tpeak but also higher ΔHdec values for the latter ones. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest Tpeak and the highest ΔHdec values. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.

Original languageEnglish
Pages (from-to)2311-2318
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - 27 Sep 2019

Fingerprint

Thermodynamic stability
Bearings (structural)
Decomposition
Triazoles
Oxygenation
Thermogravimetric analysis
Differential scanning calorimetry
Enthalpy
Temperature

Keywords

  • Differential scanning calorimetry
  • Hypervalent iodine
  • N-heterocycle
  • Stability
  • Thermogravimetry

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Thermal stability of N-heterocycle-stabilized iodanes-A systematic investigation. / Boelke, Andreas; Vlasenko, Yulia A.; Yusubov, Mekhman S.; Nachtsheim, Boris J.; Postnikov, Pavel S.

In: Beilstein Journal of Organic Chemistry, Vol. 15, 27.09.2019, p. 2311-2318.

Research output: Contribution to journalArticle

@article{1eebe010a40344a4aacc4b1e74dfe20c,
title = "Thermal stability of N-heterocycle-stabilized iodanes-A systematic investigation",
abstract = "The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl-and mesityl(aryl)-λ3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures (Tpeak) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (ΔHdec) varied from-29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high Tpeak but also higher ΔHdec values for the latter ones. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest Tpeak and the highest ΔHdec values. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.",
keywords = "Differential scanning calorimetry, Hypervalent iodine, N-heterocycle, Stability, Thermogravimetry",
author = "Andreas Boelke and Vlasenko, {Yulia A.} and Yusubov, {Mekhman S.} and Nachtsheim, {Boris J.} and Postnikov, {Pavel S.}",
year = "2019",
month = "9",
day = "27",
doi = "10.3762/bjoc.15.223",
language = "English",
volume = "15",
pages = "2311--2318",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Thermal stability of N-heterocycle-stabilized iodanes-A systematic investigation

AU - Boelke, Andreas

AU - Vlasenko, Yulia A.

AU - Yusubov, Mekhman S.

AU - Nachtsheim, Boris J.

AU - Postnikov, Pavel S.

PY - 2019/9/27

Y1 - 2019/9/27

N2 - The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl-and mesityl(aryl)-λ3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures (Tpeak) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (ΔHdec) varied from-29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high Tpeak but also higher ΔHdec values for the latter ones. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest Tpeak and the highest ΔHdec values. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.

AB - The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl-and mesityl(aryl)-λ3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures (Tpeak) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (ΔHdec) varied from-29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high Tpeak but also higher ΔHdec values for the latter ones. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest Tpeak and the highest ΔHdec values. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.

KW - Differential scanning calorimetry

KW - Hypervalent iodine

KW - N-heterocycle

KW - Stability

KW - Thermogravimetry

UR - http://www.scopus.com/inward/record.url?scp=85073112481&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85073112481&partnerID=8YFLogxK

U2 - 10.3762/bjoc.15.223

DO - 10.3762/bjoc.15.223

M3 - Article

AN - SCOPUS:85073112481

VL - 15

SP - 2311

EP - 2318

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -