NDLI: Phosphorus heterocycles: synthesis, spectroscopic study and X-ray crystallography of some new diazaphosphorinanes

Content Provider	Springer Nature Link
Author	Gholivand, Khodayar Shariatinia, Zahra Mahzouni, Hamid Reza Amiri, Shadi
Copyright Year	2007
Abstract	New diazaphosphorinanes with formula R=C$_{6}$H$_{5}$O (2), 4-CH$_{3}$-C$_{6}$H$_{4}$NH (3), 4-NO$_{2}$-C$_{6}$H$_{4}$NH (4), R=Cl (5), 4-CH$_{3}$-C$_{6}$H$_{4}$O (6), and C$_{6}$H$_{5}$NH (7) were synthesized and characterized by $^{1}$H, $^{13}$C, $^{31}$P NMR and IR spectroscopy and elemental analysis. The crystal structures of compounds 1 and (8) were determined using X-ray crystallography. In these structures, the P=O bond is placed in an equatorial position and the aliphatic six-membered rings show chair conformations. These compounds form two-dimensional polymeric chains via intermolecular P=O…H–N hydrogen bonds. $^{1}$H NMR spectrum of compound 1 shows a ddd splitting pattern for the coupling of H$_{equatorial}$ proton with phosphorus atom, H$_{axial}$ atom, and NH proton with a high-value $^{3}$ J(PNCH) coupling constant = 26.1 Hz. But, H$_{axial}$ indicates a dd splitting pattern because of the coupling with H$_{equatorial}$ and NH protons. $^{13}$C NMR spectra of compounds 5–7, indicated high values for $^{3}$ J(P,C)$_{aromatic}$ = 11.9, 11.3 and 10.2 Hz due to the coupling of the aromatic carbon atom of naphthalene moiety with the phosphorus atom. $^{31}$P NMR spectra indicate that the δ($^{31}$P) of compounds 1–4 and 8 containing NH groups connected to the aliphatic carbon atoms appear downfield relative to those of compounds 5–7 that containing NH groups connected to the aromatic naphthalene group.
Starting Page	653
Ending Page	660
Page Count	8
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	18
Issue Number	5
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2007-06-06
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Diazaphosphorinanes X-ray crystallography NMR spectroscopy Theoretical and Computational Chemistry Physical Chemistry Computer Applications in Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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