Effect of Counteranions on the Conformational Equilibrium of 1-Butyl-3-methylimidazolium-Based Ionic Liquids

<table class="table-group" width="800px"><tr class="fig-image" id="a"><td><img alt="648245.fig.001a" src="https://static.hindawi.com/articles/ijs/volume-2011/648245/figures/648245.fig.001a.jpg"/></td></tr><tr class="fig-caption"><td align="center"><table><tr><td><b>(a) </b><i>Trans-Trans</i> (<svg height="11.6125" id="M5" style="vertical-align:-0.0pt" version="1.1" viewbox="0 0 22.762501 11.6125" width="22.762501" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,11.55)"><path d="M649 676l-22 -187l-33 -2q3 56 -12 94q-8 20 -31.5 26.5t-86.5 6.5h-74l-90 -491q-4 -23 -6 -36.5t1 -25t7 -16.5t18 -9t27 -5t41 -3l-6 -28h-286l4 28q68 5 84 18.5t28 76.5l94 491h-55q-74 0 -100.5 -6t-41.5 -23q-24 -29 -54 -98l-32 1q32 98 53 188h22q7 -18 15 -22
t37 -4h417q23 0 33.5 5t25.5 21h23z" id="x1D447"></path></g><g transform="matrix(.017,-0,0,-.017,11.384,11.55)"><path d="M649 676l-22 -187l-33 -2q3 56 -12 94q-8 20 -31.5 26.5t-86.5 6.5h-74l-90 -491q-4 -23 -6 -36.5t1 -25t7 -16.5t18 -9t27 -5t41 -3l-6 -28h-286l4 28q68 5 84 18.5t28 76.5l94 491h-55q-74 0 -100.5 -6t-41.5 -23q-24 -29 -54 -98l-32 1q32 98 53 188h22q7 -18 15 -22
t37 -4h417q23 0 33.5 5t25.5 21h23z" id="x1D447"></path></g>
</svg>) conformer</td></tr></table></td></tr><tr class="fig-image" id="b"><td><img alt="648245.fig.001b" src="https://static.hindawi.com/articles/ijs/volume-2011/648245/figures/648245.fig.001b.jpg"/></td></tr><tr class="fig-caption"><td align="center"><table><tr><td><b>(b) </b><i>Gauche-Trans</i> (<svg height="11.9" id="M6" style="vertical-align:-0.23206pt" version="1.1" viewbox="0 0 23.75 11.9" width="23.75" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,11.55)"><path d="M713 296l-5 -25q-47 -7 -59 -20t-23 -72l-15 -79q-9 -48 -3 -74q-15 -3 -55 -13t-63 -15t-59.5 -10t-70.5 -5q-149 0 -243 80t-94 220q0 169 127.5 276.5t336.5 107.5q91 0 206 -36l-10 -165l-29 -1q1 85 -47.5 126t-146.5 41q-153 0 -243.5 -97t-90.5 -242
q0 -122 68.5 -198.5t188.5 -76.5q121 0 139 75l20 86q13 58 -1.5 70.5t-99.5 20.5l5 26h267z" id="x1D43A"></path></g><g transform="matrix(.017,-0,0,-.017,12.37,11.55)"><path d="M649 676l-22 -187l-33 -2q3 56 -12 94q-8 20 -31.5 26.5t-86.5 6.5h-74l-90 -491q-4 -23 -6 -36.5t1 -25t7 -16.5t18 -9t27 -5t41 -3l-6 -28h-286l4 28q68 5 84 18.5t28 76.5l94 491h-55q-74 0 -100.5 -6t-41.5 -23q-24 -29 -54 -98l-32 1q32 98 53 188h22q7 -18 15 -22
t37 -4h417q23 0 33.5 5t25.5 21h23z" id="x1D447"></path></g>
</svg>) conformer</td></tr></table></td></tr></table>

<table>Optimized structures of the (a) <i>trans-trans </i>(<svg height="11.6125" id="M3" style="vertical-align:-0.0pt" version="1.1" viewbox="0 0 22.762501 11.6125" width="22.762501" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,11.55)"><path d="M649 676l-22 -187l-33 -2q3 56 -12 94q-8 20 -31.5 26.5t-86.5 6.5h-74l-90 -491q-4 -23 -6 -36.5t1 -25t7 -16.5t18 -9t27 -5t41 -3l-6 -28h-286l4 28q68 5 84 18.5t28 76.5l94 491h-55q-74 0 -100.5 -6t-41.5 -23q-24 -29 -54 -98l-32 1q32 98 53 188h22q7 -18 15 -22
t37 -4h417q23 0 33.5 5t25.5 21h23z" id="x1D447"></path></g><g transform="matrix(.017,-0,0,-.017,11.384,11.55)"><path d="M649 676l-22 -187l-33 -2q3 56 -12 94q-8 20 -31.5 26.5t-86.5 6.5h-74l-90 -491q-4 -23 -6 -36.5t1 -25t7 -16.5t18 -9t27 -5t41 -3l-6 -28h-286l4 28q68 5 84 18.5t28 76.5l94 491h-55q-74 0 -100.5 -6t-41.5 -23q-24 -29 -54 -98l-32 1q32 98 53 188h22q7 -18 15 -22
t37 -4h417q23 0 33.5 5t25.5 21h23z" id="x1D447"></path></g>
</svg>) and (b) <i>gauche-trans </i>(<svg height="11.9" id="M4" style="vertical-align:-0.23206pt" version="1.1" viewbox="0 0 23.75 11.9" width="23.75" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,11.55)"><path d="M713 296l-5 -25q-47 -7 -59 -20t-23 -72l-15 -79q-9 -48 -3 -74q-15 -3 -55 -13t-63 -15t-59.5 -10t-70.5 -5q-149 0 -243 80t-94 220q0 169 127.5 276.5t336.5 107.5q91 0 206 -36l-10 -165l-29 -1q1 85 -47.5 126t-146.5 41q-153 0 -243.5 -97t-90.5 -242
q0 -122 68.5 -198.5t188.5 -76.5q121 0 139 75l20 86q13 58 -1.5 70.5t-99.5 20.5l5 26h267z" id="x1D43A"></path></g><g transform="matrix(.017,-0,0,-.017,12.37,11.55)"><path d="M649 676l-22 -187l-33 -2q3 56 -12 94q-8 20 -31.5 26.5t-86.5 6.5h-74l-90 -491q-4 -23 -6 -36.5t1 -25t7 -16.5t18 -9t27 -5t41 -3l-6 -28h-286l4 28q68 5 84 18.5t28 76.5l94 491h-55q-74 0 -100.5 -6t-41.5 -23q-24 -29 -54 -98l-32 1q32 98 53 188h22q7 -18 15 -22
t37 -4h417q23 0 33.5 5t25.5 21h23z" id="x1D447"></path></g>
</svg>) conformers of 1-butyl-3-methylimidazolium ([bmim]<sup>+</sup>) cation by B3LYP/6-311+(d) level.</table>

International Journal of Spectroscopy

fig1

Figure 1

Figure 1: Effect of Counteranions on the Conformational Equilibrium of 1-Butyl-3-methylimidazolium-Based Ionic Liquids 