The crystal structures of 1-(polyfluorophenylmethyl)-3-methylimidazolium bromide salts

Andrew C. Marr; Graham C. Saunders; Hayden Thomas

doi:10.1016/j.jfluchem.2020.109556

The crystal structures of 1-(polyfluorophenylmethyl)-3-methylimidazolium bromide salts

Andrew C. Marr, Graham C. Saunders^*, Hayden Thomas

^*Corresponding author for this work

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

1 Citation (Scopus)

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Abstract

The crystal structures of 1-(2,3,5,6-tetrafluorophenylmethyl)-3-methylimidazolium bromide (2), 1-(2,3,4,5-tetrafluorophenylmethyl)-3-methylimidazolium bromide (3), 1-(2,4,6-trifluorophenylmethyl)-3-methylimidazolium bromide (4) and 1-(2,3,6-trifluorophenylmethyl)-3-methylimidazolium bromide (5) have been determined. The structures contain non-covalent interactions: hydrogen bonding, anion–π and π–π stacking interactions. The strengths of these interactions have been calculated using DFT. The structures and interactions are compared with those of 1-(2,3,4,5,6-pentafluorophenylmethyl)-3-methylimidazolium bromide (1) and 1-(2,6-difluorophenylmethyl)-3-methylimidazolium bromide (6).

Original language	English
Article number	109556
Journal	Journal of Fluorine Chemistry
Volume	235
DOIs	https://doi.org/10.1016/j.jfluchem.2020.109556
Publication status	Published - 16 May 2020

Keywords

Anion–π interaction
Crystal structure
DFT calculation
Hydrogen bonding
Imidazolium salt
π–π Stacking

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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The crystal structures of 1-(polyfluorophenylmethyl)-3-methylimidazolium bromide salts
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@article{38774587c10646d98462e64aa3ce2c9b,

title = "The crystal structures of 1-(polyfluorophenylmethyl)-3-methylimidazolium bromide salts",

abstract = "The crystal structures of 1-(2,3,5,6-tetrafluorophenylmethyl)-3-methylimidazolium bromide (2), 1-(2,3,4,5-tetrafluorophenylmethyl)-3-methylimidazolium bromide (3), 1-(2,4,6-trifluorophenylmethyl)-3-methylimidazolium bromide (4) and 1-(2,3,6-trifluorophenylmethyl)-3-methylimidazolium bromide (5) have been determined. The structures contain non-covalent interactions: hydrogen bonding, anion–π and π–π stacking interactions. The strengths of these interactions have been calculated using DFT. The structures and interactions are compared with those of 1-(2,3,4,5,6-pentafluorophenylmethyl)-3-methylimidazolium bromide (1) and 1-(2,6-difluorophenylmethyl)-3-methylimidazolium bromide (6).",

keywords = "Anion–π interaction, Crystal structure, DFT calculation, Hydrogen bonding, Imidazolium salt, π–π Stacking",

author = "Marr, {Andrew C.} and Saunders, {Graham C.} and Hayden Thomas",

year = "2020",

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doi = "10.1016/j.jfluchem.2020.109556",

language = "English",

volume = "235",

journal = "Journal of Fluorine Chemistry",

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T1 - The crystal structures of 1-(polyfluorophenylmethyl)-3-methylimidazolium bromide salts

AU - Marr, Andrew C.

AU - Saunders, Graham C.

AU - Thomas, Hayden

PY - 2020/5/16

Y1 - 2020/5/16

N2 - The crystal structures of 1-(2,3,5,6-tetrafluorophenylmethyl)-3-methylimidazolium bromide (2), 1-(2,3,4,5-tetrafluorophenylmethyl)-3-methylimidazolium bromide (3), 1-(2,4,6-trifluorophenylmethyl)-3-methylimidazolium bromide (4) and 1-(2,3,6-trifluorophenylmethyl)-3-methylimidazolium bromide (5) have been determined. The structures contain non-covalent interactions: hydrogen bonding, anion–π and π–π stacking interactions. The strengths of these interactions have been calculated using DFT. The structures and interactions are compared with those of 1-(2,3,4,5,6-pentafluorophenylmethyl)-3-methylimidazolium bromide (1) and 1-(2,6-difluorophenylmethyl)-3-methylimidazolium bromide (6).

AB - The crystal structures of 1-(2,3,5,6-tetrafluorophenylmethyl)-3-methylimidazolium bromide (2), 1-(2,3,4,5-tetrafluorophenylmethyl)-3-methylimidazolium bromide (3), 1-(2,4,6-trifluorophenylmethyl)-3-methylimidazolium bromide (4) and 1-(2,3,6-trifluorophenylmethyl)-3-methylimidazolium bromide (5) have been determined. The structures contain non-covalent interactions: hydrogen bonding, anion–π and π–π stacking interactions. The strengths of these interactions have been calculated using DFT. The structures and interactions are compared with those of 1-(2,3,4,5,6-pentafluorophenylmethyl)-3-methylimidazolium bromide (1) and 1-(2,6-difluorophenylmethyl)-3-methylimidazolium bromide (6).

KW - Anion–π interaction

KW - Crystal structure

KW - DFT calculation

KW - Hydrogen bonding

KW - Imidazolium salt

KW - π–π Stacking

U2 - 10.1016/j.jfluchem.2020.109556

DO - 10.1016/j.jfluchem.2020.109556

M3 - Article

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SN - 0022-1139

VL - 235

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

M1 - 109556

ER -

The crystal structures of 1-(polyfluorophenylmethyl)-3-methylimidazolium bromide salts

Abstract

Keywords

ASJC Scopus subject areas

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