TY - JOUR
T1 - New fluorous ponytailed 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium halide salts
AU - Lu, Norman
AU - Alagesan, Mani
AU - Ho, Chi Liang
AU - Wei, Rong Jyun
AU - Kung, Chih Chieh
AU - Chang, Jung Shan
AU - Wen, Yuh Sheng
AU - Liu, Ling Kang
PY - 2016/12/1
Y1 - 2016/12/1
N2 - It is possible that fluorous compounds could be utilized as directing forces in crystal engineering for applications in materials chemistry or catalysis. Although numerous fluorous compounds have been used for various applications, their structures in the solid state remains a lively matter for debate. The reaction of 4-[(2,2,2-trifluoroethoxy)methyl]pyridine with HX (X = I or Cl) yielded new fluorous ponytailed pyridinium halide salts, namely 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium iodide, C8H9F3NO(+)·I(-), (1), and 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium chloride, C8H9F3NO(+)·Cl(-), (2), which were characterized by IR spectroscopy, multinuclei ((1)H, (13)C and (19)F) NMR spectroscopy and single-crystal X-ray diffraction. Structure analysis showed that there are two types of hydrogen bonds, namely N-H...X and C-H...X. The iodide anion in salt (1) is hydrogen bonded to three 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium cations in the crystal packing, while the chloride ion in salt (2) is involved in six hydrogen bonds to five 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium cations, which is attributed to the smaller size and reduced polarizability of the chloride ion compared to the iodide ion. In the IR spectra, the pyridinium N-H stretching band for salt (1) exhibited a blue shift compared with that of salt (2).
AB - It is possible that fluorous compounds could be utilized as directing forces in crystal engineering for applications in materials chemistry or catalysis. Although numerous fluorous compounds have been used for various applications, their structures in the solid state remains a lively matter for debate. The reaction of 4-[(2,2,2-trifluoroethoxy)methyl]pyridine with HX (X = I or Cl) yielded new fluorous ponytailed pyridinium halide salts, namely 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium iodide, C8H9F3NO(+)·I(-), (1), and 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium chloride, C8H9F3NO(+)·Cl(-), (2), which were characterized by IR spectroscopy, multinuclei ((1)H, (13)C and (19)F) NMR spectroscopy and single-crystal X-ray diffraction. Structure analysis showed that there are two types of hydrogen bonds, namely N-H...X and C-H...X. The iodide anion in salt (1) is hydrogen bonded to three 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium cations in the crystal packing, while the chloride ion in salt (2) is involved in six hydrogen bonds to five 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium cations, which is attributed to the smaller size and reduced polarizability of the chloride ion compared to the iodide ion. In the IR spectra, the pyridinium N-H stretching band for salt (1) exhibited a blue shift compared with that of salt (2).
KW - Journal Article
U2 - 10.1107/S2053229616018428
DO - 10.1107/S2053229616018428
M3 - Article
C2 - 27918304
VL - 72
SP - 1007
EP - 1011
JO - Acta crystallographica. Section C, Structural chemistry
JF - Acta crystallographica. Section C, Structural chemistry
SN - 2053-2296
IS - Pt 12
ER -