A 19F NMR study of C-I....pi- halogen bonding

Dieter Hauchecorne, Benjamin J. vand er Veken, Wouter A. Herrebout, Poul Erik Hansen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The formation of halogen bonded complexes between toluene-d8 and the perfluoroiodopropanes 1-C3F7I and 2-C3F7I has been investigated using 19F NMR spectroscopy. For both Lewis acids, evidence was found for the formation of a C–I⋯π halogen bonded complex. The complex formed is a 1:1 type. Using spectra recorded at different temperatures, the complexation enthalpies and entropies for the complexes were determined to be −2.9(1) kJ mol−1 and −19.1(2) J K−1 mol−1 for the 2-C3F7I⋅toluene-d8 complex and −2.7(1) kJ mol−1 and −16.0(4) K−1 mol−1 for the 1-C3F7I⋅toluene-d8 complex. The experimental results are supported by ab initio calculations at the B3LYP-PCM/6-311++G(d,p) + LanL2DZ∗ level.
Original languageEnglish
JournalChemical Physics
Volume381
Issue number1-3
Pages (from-to)5-10
Number of pages6
ISSN0301-0104
DOIs
Publication statusPublished - 2011

Cite this

Hauchecorne, Dieter ; vand er Veken, Benjamin J. ; Herrebout, Wouter A. ; Hansen, Poul Erik. / A 19F NMR study of C-I....pi- halogen bonding. In: Chemical Physics. 2011 ; Vol. 381, No. 1-3. pp. 5-10.
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title = "A 19F NMR study of C-I....pi- halogen bonding",
abstract = "The formation of halogen bonded complexes between toluene-d8 and the perfluoroiodopropanes 1-C3F7I and 2-C3F7I has been investigated using 19F NMR spectroscopy. For both Lewis acids, evidence was found for the formation of a C–I⋯π halogen bonded complex. The complex formed is a 1:1 type. Using spectra recorded at different temperatures, the complexation enthalpies and entropies for the complexes were determined to be −2.9(1) kJ mol−1 and −19.1(2) J K−1 mol−1 for the 2-C3F7I⋅toluene-d8 complex and −2.7(1) kJ mol−1 and −16.0(4) K−1 mol−1 for the 1-C3F7I⋅toluene-d8 complex. The experimental results are supported by ab initio calculations at the B3LYP-PCM/6-311++G(d,p) + LanL2DZ∗ level.",
keywords = "19F NMR, halogen bonding, thermodynamic data, perfluoroiodopropanes, complex, toluene",
author = "Dieter Hauchecorne and {vand er Veken}, {Benjamin J.} and Herrebout, {Wouter A.} and Hansen, {Poul Erik}",
year = "2011",
doi = "doi:10.1016/j.chemphys.2010.12.012",
language = "English",
volume = "381",
pages = "5--10",
journal = "Chemical Physics",
issn = "0301-0104",
publisher = "Elsevier BV",
number = "1-3",

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Hauchecorne, D, vand er Veken, BJ, Herrebout, WA & Hansen, PE 2011, 'A 19F NMR study of C-I....pi- halogen bonding', Chemical Physics, vol. 381, no. 1-3, pp. 5-10. https://doi.org/doi:10.1016/j.chemphys.2010.12.012

A 19F NMR study of C-I....pi- halogen bonding. / Hauchecorne, Dieter; vand er Veken, Benjamin J.; Herrebout, Wouter A.; Hansen, Poul Erik.

In: Chemical Physics, Vol. 381, No. 1-3, 2011, p. 5-10.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - A 19F NMR study of C-I....pi- halogen bonding

AU - Hauchecorne, Dieter

AU - vand er Veken, Benjamin J.

AU - Herrebout, Wouter A.

AU - Hansen, Poul Erik

PY - 2011

Y1 - 2011

N2 - The formation of halogen bonded complexes between toluene-d8 and the perfluoroiodopropanes 1-C3F7I and 2-C3F7I has been investigated using 19F NMR spectroscopy. For both Lewis acids, evidence was found for the formation of a C–I⋯π halogen bonded complex. The complex formed is a 1:1 type. Using spectra recorded at different temperatures, the complexation enthalpies and entropies for the complexes were determined to be −2.9(1) kJ mol−1 and −19.1(2) J K−1 mol−1 for the 2-C3F7I⋅toluene-d8 complex and −2.7(1) kJ mol−1 and −16.0(4) K−1 mol−1 for the 1-C3F7I⋅toluene-d8 complex. The experimental results are supported by ab initio calculations at the B3LYP-PCM/6-311++G(d,p) + LanL2DZ∗ level.

AB - The formation of halogen bonded complexes between toluene-d8 and the perfluoroiodopropanes 1-C3F7I and 2-C3F7I has been investigated using 19F NMR spectroscopy. For both Lewis acids, evidence was found for the formation of a C–I⋯π halogen bonded complex. The complex formed is a 1:1 type. Using spectra recorded at different temperatures, the complexation enthalpies and entropies for the complexes were determined to be −2.9(1) kJ mol−1 and −19.1(2) J K−1 mol−1 for the 2-C3F7I⋅toluene-d8 complex and −2.7(1) kJ mol−1 and −16.0(4) K−1 mol−1 for the 1-C3F7I⋅toluene-d8 complex. The experimental results are supported by ab initio calculations at the B3LYP-PCM/6-311++G(d,p) + LanL2DZ∗ level.

KW - 19F NMR

KW - halogen bonding

KW - thermodynamic data

KW - perfluoroiodopropanes

KW - complex

KW - toluene

U2 - doi:10.1016/j.chemphys.2010.12.012

DO - doi:10.1016/j.chemphys.2010.12.012

M3 - Journal article

VL - 381

SP - 5

EP - 10

JO - Chemical Physics

JF - Chemical Physics

SN - 0301-0104

IS - 1-3

ER -