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Syntheses and Spectroscopic Study of Some New N‐4‐Fluorobenzoyl Phosphoric Triamides; Crystal Structures of 4‐F‐C 6 H 4 C(O)N(H)P(O)R 2 , R = NH‐C(CH 3 ) 3 , NH‐CH 2 C 6 H 5 , N(CH 3 )(CH 2 C 6 H 5 )
Author(s) -
Gholivand Khodayar,
Shariatinia Zahra,
Pourayoubi Mehrdad
Publication year - 2006
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200500326
Subject(s) - chemistry , dimer , crystallography , crystal structure , hydrogen bond , molecule , moiety , amine gas treating , mass spectrum , intermolecular force , stereochemistry , nmr spectra database , phosphoric acid , spectral line , ion , organic chemistry , physics , astronomy
Some new N‐4‐Fluorobenzoyl phosphoric triamides with formula 4‐F‐C 6 H 4 C(O)N(H)P(O)X 2 , X = NH‐C(CH 3 ) 3 ( 1 ), NH‐CH 2 ‐CH=CH 2 ( 2 ), NH‐CH 2 C 6 H 5 ( 3 ), N(CH 3 )(C 6 H 5 ) ( 4 ), NH‐CH(CH 3 )(C 6 H 5 ) ( 5 ) were synthesized and characterized by 1 H, 13 C, 31 P NMR, IR and Mass spectroscopy and elemental analysis. The structures of compounds 1 , 3 and 4 were investigated by X‐ray crystallography. The P=O and C=O bonds in these compounds are anti. Compounds 1 and 3 form one dimensional polymeric chain produced by intra‐ and intermolecular ‐P=O···H‐N‐ hydrogen bonds. Compound 4 forms only a centrosymmetric dimer in the crystalline lattice via two equal ‐P=O···H‐N‐ hydrogen bonds. 1 H and 13 C NMR spectra show two series of signals for the two amine groups in compound 1 . This is also observed for the two α‐methylbenzylamine groups in 5 due to the presence of chiral carbon atom in molecule. 13 C NMR spectrum of compound 4 shows that 2 J(P,C aliphatic ) coupling constant for CH 2 group is greater than for CH 3 in agreement with our previous study. Mass spectra of compounds 1 ‐ 3 (containing 4‐F‐C 6 H 4 C(O)N(H)P(O) moiety) indicate the fragments of amidophosphoric acid and 4‐F‐C 6 H 4 CN + that formed in a pseudo McLafferty rearrangement pathway. Also, the fragments of aliphatic amines have high intensity in mass spectra.