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.
| Language | English |
|---|---|
| Pages | 396-400 |
| Number of pages | 5 |
| Journal | Zeitschrift fur Kristallografie |
| Volume | 225 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2010 |
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Keywords
- cysteine derivative
- amino acid
- zwitterion
- supramolecular analysis
- dft calculations
- single crystal structure analysis
- x-ray diffraction
- l-cysteine
- density
- diffraction
Cite this
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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 journal › Article
TY - JOUR
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
N2 - 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.
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.
KW - cysteine derivative
KW - amino acid
KW - zwitterion
KW - supramolecular analysis
KW - dft calculations
KW - single crystal structure analysis
KW - x-ray diffraction
KW - l-cysteine
KW - density
KW - diffraction
UR - http://www.scopus.com/inward/record.url?scp=79951640947&partnerID=8YFLogxK
U2 - 10.1524/zkri.2010.1270
DO - 10.1524/zkri.2010.1270
M3 - Article
VL - 225
SP - 396
EP - 400
JO - Zeitschrift fur Kristallografie
T2 - Zeitschrift fur Kristallografie
JF - Zeitschrift fur Kristallografie
SN - 0044-2968
IS - 9
ER -