X-ray crystal structure, NMR parameters, and conformational study of α-aminopropanephosphonic acid

✍ Scribed by Alan P. Bashall; John Crowder; Hagen Dronia; Gerhard Hägele; Harry R. Hudson; Rosalind J. Lee; Mary McPartlin; Ray W. Matthews; Johannes Ollig

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 504 KB
• Volume: 21
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20609

✦ Synopsis

Abstract

X‐ray structural data for α‐aminopropanephosphonic acid (APPA), together with ^1^H NMR spectroscopy including PANIC and WIN‐DAISY spectral simulation, and theoretical calculations using the programs VAMP 4.4 (PM3) and GAUSSIAN 92 (3–21G**), confirm an antistaggered relationship between the methyl and phosphonic acid groups in this zwitterionic compound, both in the solid state and in aqueous solution. ^31^P{^1^H} and ^13^C{^1^H}‐NMR controlled titrations provide information on p__K__~a~ values, proton exchange, ion‐specific chemical shifts, and coupling constants in solution. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:314–325, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20609