TY - JOUR
T1 - Two new water-soluble derivatives of 1,3,5-triaza-7-phosphaadamantane (PTA)
T2 - Synthesis, characterization, X-ray analysis and solubility studies of 3,7-diformyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane and 1-pyridylmethyl-3,5-diaza-1-azonia-7-phosphatricyclo[3.3.1.1]decane bromide
AU - Krogstad, Donald Alan
AU - Ellis, Gordon S.
AU - Gunderson, Andrew K.
AU - Hammrich, Alyssa J.
AU - Rudolf, Joseph W.
AU - Halfen, Jason A.
N1 - Funding Information:
The authors thank the Concordia College Alumni Chemistry Research Fund, the Concordia College Centennial Scholars Program and to the Donors of The Petroleum Research Fund, administered by the American Chemical Society, for partial support (Grant 33818-GB3 to D.A.K. and Grant 33450-GB3 to J.A.H.) of this research.
PY - 2007/9/20
Y1 - 2007/9/20
N2 - Two water-soluble phosphines, 3,7-diformyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (1, DFPTA) and 1-pyridylmethyl-3,5-diaza-1-azonia-7-phosphatricyclo[3.3.1.1]decane bromide (2, [pymePTA]Br), have been respectively, prepared by reacting 1,3,5-triaza-7-phosphaadamantane (PTA) with formic anhydride and bromomethylpyridine. Compound 1 is only the second acyl derivative of PTA to be prepared while 2 is only the second derivative of PTA reported that contains an aromatic appendage. Both compounds were characterized by elemental analysis, FAB-MS, 1H, 13C, and 31P NMR spectroscopy, and single crystal X-ray diffraction. This analysis showed that the formamide groups of 1 were in an anti confirmation in solution but in a syn confirmation in the solid state. The solubilities of 1 and 2 were examined in common organic solvents and water. It was found that 1.1 M aqueous solutions of 1 could be prepared while 2.4 M solutions of 2 were produced. The greater solubility of 2 was likely due to its ionic nature.
AB - Two water-soluble phosphines, 3,7-diformyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (1, DFPTA) and 1-pyridylmethyl-3,5-diaza-1-azonia-7-phosphatricyclo[3.3.1.1]decane bromide (2, [pymePTA]Br), have been respectively, prepared by reacting 1,3,5-triaza-7-phosphaadamantane (PTA) with formic anhydride and bromomethylpyridine. Compound 1 is only the second acyl derivative of PTA to be prepared while 2 is only the second derivative of PTA reported that contains an aromatic appendage. Both compounds were characterized by elemental analysis, FAB-MS, 1H, 13C, and 31P NMR spectroscopy, and single crystal X-ray diffraction. This analysis showed that the formamide groups of 1 were in an anti confirmation in solution but in a syn confirmation in the solid state. The solubilities of 1 and 2 were examined in common organic solvents and water. It was found that 1.1 M aqueous solutions of 1 could be prepared while 2.4 M solutions of 2 were produced. The greater solubility of 2 was likely due to its ionic nature.
KW - 1,3,5-Triaza-7-phosphaadamantane
KW - Ligand
KW - Phosphine
KW - Water
KW - Water-soluble
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U2 - 10.1016/j.poly.2007.05.003
DO - 10.1016/j.poly.2007.05.003
M3 - Article
AN - SCOPUS:34548251425
SN - 0277-5387
VL - 26
SP - 4093
EP - 4100
JO - Polyhedron
JF - Polyhedron
IS - 15
ER -