New fluorous ponytailed 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium halide salts

Norman Lu, Mani Alagesan, Chi Liang Ho, Rong Jyun Wei, Chih Chieh Kung, Jung Shan Chang, Yuh Sheng Wen, Ling Kang Liu

Research output: Contribution to journalArticle

Abstract

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).

Original languageEnglish
Pages (from-to)1007-1011
Number of pages5
JournalActa crystallographica. Section C, Structural chemistry
Volume72
Issue numberPt 12
DOIs
Publication statusPublished - Dec 1 2016

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halides
Salts
salts
Iodides
iodides
Chlorides
Ions
Cations
Hydrogen bonds
Positive ions
chlorides
Crystal engineering
hydrogen bonds
methyl chloride
cations
ions
blue shift
Pyridine
spectroscopy
Catalysis

Keywords

  • Journal Article

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New fluorous ponytailed 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium halide salts. / Lu, Norman; Alagesan, Mani; Ho, Chi Liang; Wei, Rong Jyun; Kung, Chih Chieh; Chang, Jung Shan; Wen, Yuh Sheng; Liu, Ling Kang.

In: Acta crystallographica. Section C, Structural chemistry, Vol. 72, No. Pt 12, 01.12.2016, p. 1007-1011.

Research output: Contribution to journalArticle

Lu, Norman ; Alagesan, Mani ; Ho, Chi Liang ; Wei, Rong Jyun ; Kung, Chih Chieh ; Chang, Jung Shan ; Wen, Yuh Sheng ; Liu, Ling Kang. / New fluorous ponytailed 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium halide salts. In: Acta crystallographica. Section C, Structural chemistry. 2016 ; Vol. 72, No. Pt 12. pp. 1007-1011.
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abstract = "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).",
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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

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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).

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