Synthesis, x-ray analysis and DFT study of 2-amino-3-(N-oxipiridin-4-ilsulfanil)-propionic acid dihydrate

Rodolfo Moreno-Fuquen, Leidy Valencia, Alan R. Kennedy, Denise Gilmour, Leandro Ribeiro

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The title compound, C8H14N2O5S 2(H2O), 2-amino-3-(N-oxipiridin-4-ilsulfanil)-propionic acid dihydrate, is obtained by the reaction of cysteine and 4-nitropyridine N-oxide in dimethylformamide, removing the NO2 group from the benzene ring and releasing nitrous acid into the solution. The molecule exists as a Zwitterion. Hydrogen bond interactions involving the title molecule and water molecules allow the formation of R-5(5)(23) edge fused rings parallel to (010). Water molecules are connected independently, forming infinite chains (wires), in square wave form, along the b-axis. The chirality of the cysteine molecule used in the synthesis is retained in the title molecule. A density functional theory (DFT) optimized structure at the B3LYP/6-311G(3df,2p) level allows comparison of calculated and experimental IR spectra.

LanguageEnglish
Pages396-400
Number of pages5
JournalZeitschrift fur Kristallografie
Volume225
Issue number9
DOIs
Publication statusPublished - 2010

Fingerprint

propionic acid
Propionic acid
x ray analysis
Density functional theory
density functional theory
X rays
Molecules
synthesis
molecules
cysteine
Cysteine
Nitrous Acid
nitrous acid
Dimethylformamide
zwitterions
Water
Chirality
rings
square waves
releasing

Keywords

  • cysteine derivative
  • amino acid
  • zwitterion
  • supramolecular analysis
  • dft calculations
  • single crystal structure analysis
  • x-ray diffraction
  • l-cysteine
  • density
  • diffraction

Cite this

Moreno-Fuquen, Rodolfo ; Valencia, Leidy ; Kennedy, Alan R. ; Gilmour, Denise ; Ribeiro, Leandro. / Synthesis, x-ray analysis and DFT study of 2-amino-3-(N-oxipiridin-4-ilsulfanil)-propionic acid dihydrate. In: Zeitschrift fur Kristallografie. 2010 ; Vol. 225, No. 9. pp. 396-400.
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abstract = "The title compound, C8H14N2O5S 2(H2O), 2-amino-3-(N-oxipiridin-4-ilsulfanil)-propionic acid dihydrate, is obtained by the reaction of cysteine and 4-nitropyridine N-oxide in dimethylformamide, removing the NO2 group from the benzene ring and releasing nitrous acid into the solution. The molecule exists as a Zwitterion. Hydrogen bond interactions involving the title molecule and water molecules allow the formation of R-5(5)(23) edge fused rings parallel to (010). Water molecules are connected independently, forming infinite chains (wires), in square wave form, along the b-axis. The chirality of the cysteine molecule used in the synthesis is retained in the title molecule. A density functional theory (DFT) optimized structure at the B3LYP/6-311G(3df,2p) level allows comparison of calculated and experimental IR spectra.",
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Synthesis, x-ray analysis and DFT study of 2-amino-3-(N-oxipiridin-4-ilsulfanil)-propionic acid dihydrate. / Moreno-Fuquen, Rodolfo; Valencia, Leidy; Kennedy, Alan R.; Gilmour, Denise; Ribeiro, Leandro.

In: Zeitschrift fur Kristallografie, Vol. 225, No. 9, 2010, p. 396-400.

Research output: Contribution to journalArticle

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T1 - Synthesis, x-ray analysis and DFT study of 2-amino-3-(N-oxipiridin-4-ilsulfanil)-propionic acid dihydrate

AU - Moreno-Fuquen, Rodolfo

AU - Valencia, Leidy

AU - Kennedy, Alan R.

AU - Gilmour, Denise

AU - Ribeiro, Leandro

PY - 2010

Y1 - 2010

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AB - The title compound, C8H14N2O5S 2(H2O), 2-amino-3-(N-oxipiridin-4-ilsulfanil)-propionic acid dihydrate, is obtained by the reaction of cysteine and 4-nitropyridine N-oxide in dimethylformamide, removing the NO2 group from the benzene ring and releasing nitrous acid into the solution. The molecule exists as a Zwitterion. Hydrogen bond interactions involving the title molecule and water molecules allow the formation of R-5(5)(23) edge fused rings parallel to (010). Water molecules are connected independently, forming infinite chains (wires), in square wave form, along the b-axis. The chirality of the cysteine molecule used in the synthesis is retained in the title molecule. A density functional theory (DFT) optimized structure at the B3LYP/6-311G(3df,2p) level allows comparison of calculated and experimental IR spectra.

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