
% T_m ~ 261 K and T_g ~ 183 K.
@article{2004-Yoshida-IC-43-1458,
    author = {<NAME> <NAME> <NAME> <NAME>},
    title = {1-Ethyl-3-methylimidazolium Based Ionic Liquids Containing Cyano Groups:  Synthesis, Characterization, and Crystal Structure},
    journal = {Inorg. Chem.},
    volume = {43},
    number = {4},
    pages = {1458--1462},
    year = {2004},
    doi = {10.1021/ic035045q},
    %note ={PMID: 14966983},
    URL = {https://doi.org/10.1021/ic035045q},
    % eprint = {https://doi.org/10.1021/ic035045q},
    abstract = {New 1-ethyl-3-methylimidazolium (EMI) salts [EMI][C(CN)3] and [EMI][Ag(CN)2] were prepared and characterized. The C(CN)3 salt has a melting point at −11 °C and shows a low viscosity (18 cP) and a high ionic conductivity (1.8 × 10-2 S cm-1) at room temperature. This conductivity is less than that of [EMI][N(CN)2] salt (2.7 × 10-2 S cm-1), possibly due to the larger molecular weight of the anion. The first EMI salt containing Ag(I) complexes [EMI][Ag(CN)2] has a higher melting point of 73 °C. In the crystal, the C−H···π interionic interactions between cations construct zigzag chains in the cationic two-dimensional layer. Close Ag··Ag interionic contacts of 3.226(1) Å were observed in the one-dimensional anionic chain, and the relatively high melting point among the EMI salts with a monoanion appears to be governed essentially by these direct Ag···Ag interactions.}
}

% T_m ~ 252-268 K, T_g ~ 169-183 K.
% see refs. 31-35
@article{2019-Bernardino-JPCB-123-9418,
    author = {<NAME>, <NAME>. and Ribeiro, <NAME>.},
    title = {Low-Temperature Phase Transitions of the Ionic Liquid 1-Ethyl-3-methylimidazolium Dicyanamide},
    journal = {J. Phys. Chem. B},
    volume = {123},
    number = {44},
    pages = {9418--9427},
    year = {2019},
    doi = {10.1021/acs.jpcb.9b07654},
    %note ={PMID: 31599592},
    URL = {https://doi.org/10.1021/acs.jpcb.9b07654},
    %eprint = {https://doi.org/10.1021/acs.jpcb.9b07654},
    abstract = {Several calorimetric measurements have shown that 1-ethyl-3-methylimidazolium dicyanamide, [C2C1im][N(CN)2], is a glass-forming liquid, even though it is a low-viscous liquid at room temperature. Here, we found slow crystallization during cooling of [C2C1im][N(CN)2] along Raman spectroscopy measurements. The low-frequency range of the Raman spectrum shows that the same crystalline phase is obtained at 210 K either by cooling or by reheating the glass (cold-crystallization). Another crystalline phase is formed at ca. 260 K just prior the melting at 270 K. X-ray diffraction and calorimetric measurements confirm that there are two crystalline phases of [C2C1im][N(CN)2]. The Raman spectra indicate that polymorphism is related to [C2C1im]+ with the ethyl chain on the plane of the imidazolium ring (the low-temperature crystal) or nonplanar (the high-temperature crystal). The structural reason for the glass-forming ability of [C2C1im][N(CN)2], despite the relatively simple molecular structures of the ions, was pursued by quantum chemistry calculations and molecular dynamics (MD) simulations. Density functional theory calculations were performed for ionic pairs in order to draw free-energy surfaces of the anion around the cation. The MD simulations using a polarizable model provided maps of occurrence of anions around cations. Both the quantum and classical calculations suggest that the delocalization of preferred positions of the anion around the cation, which adopts different conformations of the ethyl chain, is on the origin of the crystallization being hampered during cooling and the resulting glass-forming ability of [C2C1im][N(CN)2].}
}

