Ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic, succinic). Crystal structure and cation-anion interaction

V. S. Fundamensky, T. A. Kochina, Y. A. Kondratenko, A. A. Zolotarev, Yu G. Vlasov, I. S. Ignatyev

Research output

19 Citations (Scopus)

Abstract

The series of ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic and succinic) was synthesized, characterized by IR and H1, C13 NMR spectroscopy, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Their structure was determined by single-crystal X-ray diffraction. It was found that triethanolammonium [(HOCH2CH2)3NH]+ cations in salts of oxalic (1), malonic (2) and succinic acids (3) containing monoanions [OOC(CH2)nCOOH] (n = 0–2) have the endo conformation and the ammonium proton (Ham) resides inside the “lampshade” formed by three CH2CH2OH branches connected with nitrogen atom. The asymmetric cell of the second modification of the succinic acid salt (4) includes two triethanolammonium cations and a succinate dianion [(HOCH2CH2)3NH]2+[OOC(CH2)2COO]2 −. In this salt (4) one CH2CH2OH branch of the triethanolammonium cation is rotated around the N[sbnd]C bond (endo-exo conformation) and forms infinite TEA chains. This pattern was firstly found in organic salts of TEA. The obtained results show that different structures of triethanolammonium cations in the salts of dicarboxylic acids have significant influence on the cation-anion interaction.

Original languageEnglish
Pages (from-to)113-120
Number of pages8
JournalJournal of Molecular Liquids
Volume230
DOIs
Publication statusPublished - 1 Mar 2017

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Ionic Liquids
Dicarboxylic Acids
Oxalic acid
dicarboxylic acids
Succinic Acid
Ionic liquids
Anions
Cations
Negative ions
Salts
Crystal structure
Positive ions
anions
salts
cations
crystal structure
liquids
interactions
Acids
Conformations

Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Atomic and Molecular Physics, and Optics
  • Condensed Matter Physics
  • Spectroscopy
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Fundamensky, V. S. ; Kochina, T. A. ; Kondratenko, Y. A. ; Zolotarev, A. A. ; Vlasov, Yu G. ; Ignatyev, I. S. / Ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic, succinic). Crystal structure and cation-anion interaction. In: Journal of Molecular Liquids. 2017 ; Vol. 230. pp. 113-120.
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abstract = "The series of ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic and succinic) was synthesized, characterized by IR and H1, C13 NMR spectroscopy, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Their structure was determined by single-crystal X-ray diffraction. It was found that triethanolammonium [(HOCH2CH2)3NH]+ cations in salts of oxalic (1), malonic (2) and succinic acids (3) containing monoanions [OOC(CH2)nCOOH]− (n = 0–2) have the endo conformation and the ammonium proton (Ham) resides inside the “lampshade” formed by three CH2CH2OH branches connected with nitrogen atom. The asymmetric cell of the second modification of the succinic acid salt (4) includes two triethanolammonium cations and a succinate dianion [(HOCH2CH2)3NH]2+[OOC(CH2)2COO]2 −. In this salt (4) one CH2CH2OH branch of the triethanolammonium cation is rotated around the N[sbnd]C bond (endo-exo conformation) and forms infinite TEA chains. This pattern was firstly found in organic salts of TEA. The obtained results show that different structures of triethanolammonium cations in the salts of dicarboxylic acids have significant influence on the cation-anion interaction.",
keywords = "Dicarboxylic acid, IR spectra, Protic ionic liquids, Triethanolamine, Triethanolammonium salts, X-ray diffraction structure",
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Ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic, succinic). Crystal structure and cation-anion interaction. / Fundamensky, V. S.; Kochina, T. A.; Kondratenko, Y. A.; Zolotarev, A. A.; Vlasov, Yu G.; Ignatyev, I. S.

In: Journal of Molecular Liquids, Vol. 230, 01.03.2017, p. 113-120.

Research output

TY - JOUR

T1 - Ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic, succinic). Crystal structure and cation-anion interaction

AU - Fundamensky, V. S.

AU - Kochina, T. A.

AU - Kondratenko, Y. A.

AU - Zolotarev, A. A.

AU - Vlasov, Yu G.

AU - Ignatyev, I. S.

PY - 2017/3/1

Y1 - 2017/3/1

N2 - The series of ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic and succinic) was synthesized, characterized by IR and H1, C13 NMR spectroscopy, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Their structure was determined by single-crystal X-ray diffraction. It was found that triethanolammonium [(HOCH2CH2)3NH]+ cations in salts of oxalic (1), malonic (2) and succinic acids (3) containing monoanions [OOC(CH2)nCOOH]− (n = 0–2) have the endo conformation and the ammonium proton (Ham) resides inside the “lampshade” formed by three CH2CH2OH branches connected with nitrogen atom. The asymmetric cell of the second modification of the succinic acid salt (4) includes two triethanolammonium cations and a succinate dianion [(HOCH2CH2)3NH]2+[OOC(CH2)2COO]2 −. In this salt (4) one CH2CH2OH branch of the triethanolammonium cation is rotated around the N[sbnd]C bond (endo-exo conformation) and forms infinite TEA chains. This pattern was firstly found in organic salts of TEA. The obtained results show that different structures of triethanolammonium cations in the salts of dicarboxylic acids have significant influence on the cation-anion interaction.

AB - The series of ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic and succinic) was synthesized, characterized by IR and H1, C13 NMR spectroscopy, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Their structure was determined by single-crystal X-ray diffraction. It was found that triethanolammonium [(HOCH2CH2)3NH]+ cations in salts of oxalic (1), malonic (2) and succinic acids (3) containing monoanions [OOC(CH2)nCOOH]− (n = 0–2) have the endo conformation and the ammonium proton (Ham) resides inside the “lampshade” formed by three CH2CH2OH branches connected with nitrogen atom. The asymmetric cell of the second modification of the succinic acid salt (4) includes two triethanolammonium cations and a succinate dianion [(HOCH2CH2)3NH]2+[OOC(CH2)2COO]2 −. In this salt (4) one CH2CH2OH branch of the triethanolammonium cation is rotated around the N[sbnd]C bond (endo-exo conformation) and forms infinite TEA chains. This pattern was firstly found in organic salts of TEA. The obtained results show that different structures of triethanolammonium cations in the salts of dicarboxylic acids have significant influence on the cation-anion interaction.

KW - Dicarboxylic acid

KW - IR spectra

KW - Protic ionic liquids

KW - Triethanolamine

KW - Triethanolammonium salts

KW - X-ray diffraction structure

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U2 - 10.1016/j.molliq.2016.12.111

DO - 10.1016/j.molliq.2016.12.111

M3 - Article

AN - SCOPUS:85009253217

VL - 230

SP - 113

EP - 120

JO - Journal of Molecular Liquids

JF - Journal of Molecular Liquids

SN - 0167-7322

ER -