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Dependence of the long‐range phosphorus–hydrogen coupling constant n J P–H ( n = 3,6,7) on the bond order between phosphorus and its substituents: preparation and spectroscopic characterization of several phosphoramidates
Author(s) -
Gholivand Khodayar,
Ghadimi Said,
Naderimanesh Hossein,
Forouzanfar Akbar
Publication year - 2001
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.928
Subject(s) - chemistry , coupling constant , molecule , hydrogen bond , phosphorus , crystallography , stereochemistry , analytical chemistry (journal) , organic chemistry , physics , particle physics
The examination of spectra of a selected series of phosphoramidates showed that, in addition to a double bond, whenever there are one or two partial multiple bonds in the molecule the long‐range coupling constant, such as 6 J P–H , 7 J P–H and 3 J P–H , either disappears or at least reduces. In particular, the experimental data indicate the unexpected effect of a partial multiple bond between phosphorus and fluorine in 7 J P–H and 3 J P–H . The preparation of the compounds p ‐CH 3 C 6 H 4 NHP(O)Cl 2 (II), p ‐CH 3 C 6 H 4 NHP(O)(Cl)OC 6 H 4 CH 3 ‐ p (XIV), m ‐CH 3 C 6 H 4 NHP(O)(Cl)OC 6 H 4 CH 3 ‐ p (XV), m ‐CH 3 C 6 H 4 NHP(O)(Cl)OC 6 H 4 CH 3 ‐ m (XVI) and the rigid molecule CH 3 C 6 H 3 (NH) 2 P(O)Cl (XVII) are described and they are characterized by 1 H, 13 C, 31 P NMR, IR spectroscopy and elemental analysis. Copyright © 2001 John Wiley & Sons, Ltd.