Comparing the Halogen Bond to the Hydrogen Bond by Solid-State NMR Spectroscopy: Anion Coordinated Dimers from 2- and 3-Iodoethynylpyridine Salts

Chemistry : a European Journal
Patrick M J SzellDavid L Bryce

Abstract

Halogen bonding is an increasingly important tool in crystal engineering, and measuring its influence on the local chemical and electronic environment is necessary to fully understand this interaction. Here, we present a systematic crystallographic and solid-state NMR study of self-complementary halogen-bonded frameworks built from the halide salts (HCl, HBr, HI, HI3 ) of 2-iodoethynylpyridine and 3-iodoethynylpyridine. A series of single crystal X-ray structures reveals the formation of discrete charged dimers in the solid state, directed by simultaneous X- ⋅⋅⋅H-N+ hydrogen bonds and C-I⋅⋅⋅X- halogen bonds (X=Cl, Br, I). Each compound was studied using multinuclear solid-state magnetic resonance spectroscopy, observing 1 H to investigate the hydrogen bonds and 13 C, 35 Cl, and 79/81 Br to investigate the halogen bonds. A natural localized molecular orbital analysis was employed to help interpret the experimental results. 1 H SSNMR spectroscopy reveals a decrease in the chemical shift of the proton participating in the hydrogen bond as the halogen increases in size, whereas the 13 C SSNMR reveals an increased 13 C chemical shift of the C-I carbon for C-I⋅⋅⋅X- relative to C-I⋅⋅⋅N halogen bonds. Additionally, 35 Cl and 79/81 Br S...Continue Reading

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Citations

Jan 30, 2020·Physical Chemistry Chemical Physics : PCCP·Vijith KumarDavid L Bryce
Feb 12, 2020·Physical Chemistry Chemical Physics : PCCP·Miroslav Medved'Robert Zaleśny
Mar 24, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Wiktor ZierkiewiczSteve Scheiner
Apr 15, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Rafal WysokinskiSteve Scheiner
Jun 12, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·David L Bryce
Aug 7, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jia Lu, Steve Scheiner
Feb 20, 2021·Physical Chemistry Chemical Physics : PCCP·Rafał WysokińskiSteve Scheiner
Jun 4, 2021·The Journal of Physical Chemistry. a·Jordan Lapp, Steve Scheiner
Jul 12, 2019·The Journal of Physical Chemistry. a·Yijue XuDavid L Bryce

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