A strong cis-effect in an imidazole-imidazolium-substituted alkene

Dayne C. Georgiou; Mohammad A. Haghighatbin; Conor F. Hogan; Michael S. Scholz; James N. Bull; Evan J. Bieske; David J. D. Wilson; Jason L. Dutton

doi:10.1002/anie.201702287

A strong cis-effect in an imidazole-imidazolium-substituted alkene

Dayne C. Georgiou, Mohammad A. Haghighatbin, Conor F. Hogan, Michael S. Scholz, James N. Bull, Evan J. Bieske, David J. D. Wilson, Jason L. Dutton

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

5 Citations (Scopus)

Abstract

We report the first example of an alkene with two carbon-bound substituents (imidazole and imidazolium rings) where the Z-isomer has a greater thermodynamic stability than the E-isomer which persists in both the gas phase and in solution. Theoretical calculations, solution fluorescence spectroscopy and gas-phase ion mobility mass spectrometry studies confirm the preference for the Z-isomer, the stability of which is traced to a non-covalent interaction between the imidazole lone pair and the imidazolium ring.

Original language	English
Pages (from-to)	8473-8480
Number of pages	8
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	29
Early online date	21 Apr 2017
DOIs	https://doi.org/10.1002/anie.201702287
Publication status	Published - 5 Jul 2017

Keywords

cis-effect
conformation analysis
E–Z isomerization
nitrogen heterocycles

Access to Document

10.1002/anie.201702287

Cite this

@article{24bd9dba67124458ad0a7492228a3a0f,

title = "A strong cis-effect in an imidazole-imidazolium-substituted alkene",

abstract = "We report the first example of an alkene with two carbon-bound substituents (imidazole and imidazolium rings) where the Z-isomer has a greater thermodynamic stability than the E-isomer which persists in both the gas phase and in solution. Theoretical calculations, solution fluorescence spectroscopy and gas-phase ion mobility mass spectrometry studies confirm the preference for the Z-isomer, the stability of which is traced to a non-covalent interaction between the imidazole lone pair and the imidazolium ring.",

keywords = "cis-effect, conformation analysis, E–Z isomerization, nitrogen heterocycles",

author = "Georgiou, {Dayne C.} and Haghighatbin, {Mohammad A.} and Hogan, {Conor F.} and Scholz, {Michael S.} and Bull, {James N.} and Bieske, {Evan J.} and Wilson, {David J. D.} and Dutton, {Jason L.}",

year = "2017",

month = jul,

day = "5",

doi = "10.1002/anie.201702287",

language = "English",

volume = "56",

pages = "8473--8480",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley",

number = "29",

}

TY - JOUR

T1 - A strong cis-effect in an imidazole-imidazolium-substituted alkene

AU - Georgiou, Dayne C.

AU - Haghighatbin, Mohammad A.

AU - Hogan, Conor F.

AU - Scholz, Michael S.

AU - Bull, James N.

AU - Bieske, Evan J.

AU - Wilson, David J. D.

AU - Dutton, Jason L.

PY - 2017/7/5

Y1 - 2017/7/5

N2 - We report the first example of an alkene with two carbon-bound substituents (imidazole and imidazolium rings) where the Z-isomer has a greater thermodynamic stability than the E-isomer which persists in both the gas phase and in solution. Theoretical calculations, solution fluorescence spectroscopy and gas-phase ion mobility mass spectrometry studies confirm the preference for the Z-isomer, the stability of which is traced to a non-covalent interaction between the imidazole lone pair and the imidazolium ring.

AB - We report the first example of an alkene with two carbon-bound substituents (imidazole and imidazolium rings) where the Z-isomer has a greater thermodynamic stability than the E-isomer which persists in both the gas phase and in solution. Theoretical calculations, solution fluorescence spectroscopy and gas-phase ion mobility mass spectrometry studies confirm the preference for the Z-isomer, the stability of which is traced to a non-covalent interaction between the imidazole lone pair and the imidazolium ring.

KW - cis-effect

KW - conformation analysis

KW - E–Z isomerization

KW - nitrogen heterocycles

UR - http://www.scopus.com/inward/record.url?scp=85018656033&partnerID=8YFLogxK

U2 - 10.1002/anie.201702287

DO - 10.1002/anie.201702287

M3 - Article

C2 - 28429451

AN - SCOPUS:85018656033

SN - 1433-7851

VL - 56

SP - 8473

EP - 8480

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 29

ER -

A strong cis-effect in an imidazole-imidazolium-substituted alkene

Abstract

Keywords

Access to Document

Other files and links

Cite this