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Syntheses, crystal structures and dynamic 1 H NMR study of diastereotopic CH2 protons in several new phosphoric triamides

Syntheses, crystal structures and dynamic 1 H NMR study of diastereotopic CH2 protons in several... Several phosphoric triamides with formula C6H5C(O)N(H)P(O)X2, X = N(C2H5)(CH2C6H5) (1), NC4H8 (2), NH-CH2-C6H5 (3), NH-CH2-(2-Cl-C6H4) (4), NH-CH2-CH(C2H5)(C4H9) (5), N(C2H5)2 (6) and P(O)(NH-CH2-C6H5)3 (7) were synthesized and characterized by 1 H, 13 C, 31 P NMR and IR spectroscopy and elemental analysis. The structures were determined for compounds 3, 7 and 36, 4-F-C6H4C(O)NHP(O)(NH-CH2-CH=CH2)2. In compound 3, there are intermolecular -P=O … H-N- and -C=O … H-N- hydrogen bonds which form a one-dimensional polymeric chain. Compound 7 contains intermolecular -P=O … H-N- hydrogen bonds leading to a one-dimensional polymeric chain. Compound 36 forms intermolecular -P=O … H-N-, -C=O … H-N- and -C-F … H-N- hydrogen bonds which produce a three-dimensional polymeric chain in the crystalline network. The effects of rotation, ring inversion, temperature and solvent on the coupling patterns of the CH2 protons in 1 H NMR spectra were discussed. The Gibbs free energy for the rotation around the P-N bond in compounds 3, 6 and 41, (4-CH3-C6H4-O)P(O)Cl(N(CH3)(CH2C6H5)), were calculated from dynamic 1 H NMR spectra at low temperatures. The ΔG # value for compound 3 is the greatest one among these molecules. The crystal structures of compounds 3 and 6 indicates that the slightly smaller P-Namine bond lengths in 3 relative to 6 cause a greater ΔG # value in 3. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Main Group Chemistry IOS Press

Syntheses, crystal structures and dynamic 1 H NMR study of diastereotopic CH2 protons in several new phosphoric triamides

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Publisher
IOS Press
Copyright
Copyright © 2006 by IOS Press, Inc
ISSN
1024-1221
eISSN
1745-1167
DOI
10.1080/10241220601004924
Publisher site
See Article on Publisher Site

Abstract

Several phosphoric triamides with formula C6H5C(O)N(H)P(O)X2, X = N(C2H5)(CH2C6H5) (1), NC4H8 (2), NH-CH2-C6H5 (3), NH-CH2-(2-Cl-C6H4) (4), NH-CH2-CH(C2H5)(C4H9) (5), N(C2H5)2 (6) and P(O)(NH-CH2-C6H5)3 (7) were synthesized and characterized by 1 H, 13 C, 31 P NMR and IR spectroscopy and elemental analysis. The structures were determined for compounds 3, 7 and 36, 4-F-C6H4C(O)NHP(O)(NH-CH2-CH=CH2)2. In compound 3, there are intermolecular -P=O … H-N- and -C=O … H-N- hydrogen bonds which form a one-dimensional polymeric chain. Compound 7 contains intermolecular -P=O … H-N- hydrogen bonds leading to a one-dimensional polymeric chain. Compound 36 forms intermolecular -P=O … H-N-, -C=O … H-N- and -C-F … H-N- hydrogen bonds which produce a three-dimensional polymeric chain in the crystalline network. The effects of rotation, ring inversion, temperature and solvent on the coupling patterns of the CH2 protons in 1 H NMR spectra were discussed. The Gibbs free energy for the rotation around the P-N bond in compounds 3, 6 and 41, (4-CH3-C6H4-O)P(O)Cl(N(CH3)(CH2C6H5)), were calculated from dynamic 1 H NMR spectra at low temperatures. The ΔG # value for compound 3 is the greatest one among these molecules. The crystal structures of compounds 3 and 6 indicates that the slightly smaller P-Namine bond lengths in 3 relative to 6 cause a greater ΔG # value in 3.

Journal

Main Group ChemistryIOS Press

Published: Jan 1, 2006

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