Stereodynamics of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane: Experimental and theoretical analysis

Bagrat A. Shainyan; Vladimir I. Meshcheryakov; Alexandr I. Albanov; Mark V. Sigalov

doi:10.1016/j.tetlet.2005.07.068

Stereodynamics of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane: Experimental and theoretical analysis

Bagrat A. Shainyan, Vladimir I. Meshcheryakov, Alexandr I. Albanov, Mark V. Sigalov

Department of Chemistry

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

16 Scopus citations

Abstract

Dynamic NMR of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane reveals two dynamic processes: ring inversion leading to equilibrium between two degenerate rotamers of C_s symmetry (ΔG^≠ = 13.5 kcal/mol), and rotation about the S-N bond leading to equilibrium between the C_s (more stable) and C_3v (2.12 kcal/mol less stable) rotamers (ΔG^≠ = 13.0 kcal/mol).

Original language	English
Pages (from-to)	6199-6201
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2005.07.068
State	Published - 12 Sep 2005

Keywords

Conformational analysis
Density functional calculations
Dynamic NMR
Tris(triflyl) substituted symm-triazinane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Stereodynamics of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane: Experimental and theoretical analysis",

abstract = "Dynamic NMR of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane reveals two dynamic processes: ring inversion leading to equilibrium between two degenerate rotamers of Cs symmetry (ΔG≠ = 13.5 kcal/mol), and rotation about the S-N bond leading to equilibrium between the Cs (more stable) and C3v (2.12 kcal/mol less stable) rotamers (ΔG≠ = 13.0 kcal/mol).",

keywords = "Conformational analysis, Density functional calculations, Dynamic NMR, Tris(triflyl) substituted symm-triazinane",

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T1 - Stereodynamics of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane

T2 - Experimental and theoretical analysis

AU - Shainyan, Bagrat A.

AU - Meshcheryakov, Vladimir I.

AU - Albanov, Alexandr I.

AU - Sigalov, Mark V.

PY - 2005/9/12

Y1 - 2005/9/12

N2 - Dynamic NMR of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane reveals two dynamic processes: ring inversion leading to equilibrium between two degenerate rotamers of Cs symmetry (ΔG≠ = 13.5 kcal/mol), and rotation about the S-N bond leading to equilibrium between the Cs (more stable) and C3v (2.12 kcal/mol less stable) rotamers (ΔG≠ = 13.0 kcal/mol).

AB - Dynamic NMR of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane reveals two dynamic processes: ring inversion leading to equilibrium between two degenerate rotamers of Cs symmetry (ΔG≠ = 13.5 kcal/mol), and rotation about the S-N bond leading to equilibrium between the Cs (more stable) and C3v (2.12 kcal/mol less stable) rotamers (ΔG≠ = 13.0 kcal/mol).

KW - Conformational analysis

KW - Density functional calculations

KW - Dynamic NMR

KW - Tris(triflyl) substituted symm-triazinane

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DO - 10.1016/j.tetlet.2005.07.068

M3 - Article

AN - SCOPUS:23744481638

SN - 0040-4039

VL - 46

SP - 6199

EP - 6201

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Stereodynamics of 1,3,5-tris(trifluoromethylsulfonyl)-1,3,5-triazinane: Experimental and theoretical analysis

Abstract

Keywords

ASJC Scopus subject areas

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