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2 J(P,C) and 3 J(P,C) Coupling Constants in Some New Phosphoramidates. Crystal Structures of CF 3 C(O)N(H)P(O)[N(CH 3 )(CH 2 C 6 H 5 )] 2 and4‐NO 2 ‐C 6 H 4 N(H)P(O)[4‐CH 3 ‐NC 5 H 9 ] 2
Author(s) -
Gholivand Khodayar,
Shariatinia Zahra,
Pourayoubi Mehrdad
Publication year - 2005
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.200400517
Subject(s) - chemistry , moiety , dimer , molecule , hydrogen bond , ring (chemistry) , crystal structure , amine gas treating , crystallography , stereochemistry , intermolecular force , nmr spectra database , nuclear magnetic resonance spectroscopy , spectral line , organic chemistry , physics , astronomy
Some new phosphoramidates were synthesized and characterized by 1 H, 13 C, 31 P NMR, IR spectroscopy and elemental analysis. The structures of CF 3 C(O)N(H)P(O)[N(CH 3 )(CH 2 C 6 H 5 )] 2 ( 1 ) and 4‐NO 2 ‐C 6 H 4 N(H)P(O)[4‐CH 3 ‐NC 5 H 9 ] 2 ( 6 ) were confirmed by X‐ray single crystal determination. Compound 1 forms a centrosymmetric dimer and compound 6 forms a polymeric zigzag chain, both via ‐N‐H…O=P‐ intermolecular hydrogen bonds. Also, weak C‐H…F and C‐H…O hydrogen bonds were observed in compounds 1 and 6 , respectively. 13 C NMR spectra were used for study of 2 J(P,C) and 3 J(P,C) coupling constants that were showed in the molecules containing N(C 2 H 5 ) 2 and N(C 2 H 5 )(CH 2 C 6 H 5 ) moieties, 2 J(P,C)> 3 J(P,C). A contrast result was obtained for the compounds involving a five‐membered ring aliphatic amine group, NC 4 H 8 . 2 J(P,C) for N(C 2 H 5 ) 2 moiety and in NC 4 H 8 are nearly the same, but 3 J(P, C) values are larger than those in molecules with a pyrrolidinyl ring. This comparison was done for compounds with six and seven‐membered ring amine groups. In compounds with formula XP(O)[N(CH 2 R)(CH 2 C 6 H 5 )] 2 , 2 J(P,CH 2 ) benzylic > 2 J(P,CH 2 ) aliphatic , in an agreement with our previous study.