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DOAJ Open Access 2024

(<i>R</i>)-2-Amino-1-hydroxyethylphosphonic Acid

Majid Motevalli Isaac Abrahams Peter Blakskjær Caroline E. Wyatt Peter B. Wyatt
Lihat Sumber DOI

Abstrak

(<i>R</i>)-2-Amino-1-hydroxyethylphosphonic acid <b>2</b> was prepared by hydrolytic kinetic resolution of <i>rac</i>-diethyl oxiran-2-ylphosphonate followed by reaction with benzylamine, acid hydrolysis, catalytic hydrogenolysis, and anion-exchange chromatography. Recrystallization from water-ethanol gave pure <b>2</b>, which was characterized by IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, <sup>31</sup>P NMR, polarimetry, elemental microanalysis, high-resolution mass spectrometry, and single-crystal X-ray diffraction. The acid <b>2</b> crystallized in the orthorhombic noncentrosymmetric space group <i>P</i>2<sub>1</sub>2<sub>1</sub>2<sub>1</sub> with cell parameters <i>a</i> = 6.303 (2) Å, <i>b</i> = 7.104 (2) Å, <i>c</i> = 11.627 (3) Å. The X-ray crystal structure confirmed the (<i>R</i>)-configuration of <b>2</b> and revealed that <b>2</b> is zwitterionic in the solid state, with extensive intermolecular hydrogen bonding between the hydroxyl, ammonium cation, and phosphonate anion groups.

Topik & Kata Kunci

Inorganic chemistry

Penulis (5)

M

Majid Motevalli

I

Isaac Abrahams

P

Peter Blakskjær

C

Caroline E. Wyatt

P

Peter B. Wyatt

Format Sitasi

APA MLA BibTeX
Motevalli, M., Abrahams, I., Blakskjær, P., Wyatt, C.E., Wyatt, P.B. (2024). (<i>R</i>)-2-Amino-1-hydroxyethylphosphonic Acid. https://doi.org/10.3390/M1888

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Informasi Jurnal
Tahun Terbit
2024
Sumber Database
DOAJ
DOI
10.3390/M1888
Akses
Open Access ✓