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Phosphoramides: Synthesis, Spectroscopy, and X‐ray Crystallography

Phosphoramides: Synthesis, Spectroscopy, and X‐ray Crystallography ABSTRACT A series of new phosphoramides with general formula RP(O)X2, where R = amino/p‐methylphenoxy and X = amine, were synthesized and characterized by 1H, 13C, 31P nuclear magnetic resonance (NMR), and infrared (IR) spectroscopy and elemental analysis. The 31P{1H} NMR spectra show that among compounds 7–9 containing 2‐, 3‐, and 4‐aminopyridinyl moieties, respectively, the shielding order of the P atom decreases as 7 > 9 > 8. Also, the structure of compound 7 was determined by X‐ray crystallography. In this structure, repeated noncentrosymmetric dimers are formed by two strong intermolecular N(1)‐H(1N)…N(2) and N(3)‐H(3N)…O(1) hydrogen bonds. Taking into account weak intermolecular C(17)‐H(17C)…N(4), C(17)‐H(17E)…N(4), C(2)‐H(2A)…O(2), and also weak aromatic C—H…C interactions, a three‐dimensional polymeric chain is created in the crystalline network. The density functional theory calculations at B3LYP, B3PW91, and M06 levels using the 6–31+G** basis set were in good agreement with the X‐ray crystallography data. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Phosphoramides: Synthesis, Spectroscopy, and X‐ray Crystallography

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References (30)

Publisher
Wiley
Copyright
Copyright © 2013 Wiley Periodicals, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.21107
Publisher site
See Article on Publisher Site

Abstract

ABSTRACT A series of new phosphoramides with general formula RP(O)X2, where R = amino/p‐methylphenoxy and X = amine, were synthesized and characterized by 1H, 13C, 31P nuclear magnetic resonance (NMR), and infrared (IR) spectroscopy and elemental analysis. The 31P{1H} NMR spectra show that among compounds 7–9 containing 2‐, 3‐, and 4‐aminopyridinyl moieties, respectively, the shielding order of the P atom decreases as 7 > 9 > 8. Also, the structure of compound 7 was determined by X‐ray crystallography. In this structure, repeated noncentrosymmetric dimers are formed by two strong intermolecular N(1)‐H(1N)…N(2) and N(3)‐H(3N)…O(1) hydrogen bonds. Taking into account weak intermolecular C(17)‐H(17C)…N(4), C(17)‐H(17E)…N(4), C(2)‐H(2A)…O(2), and also weak aromatic C—H…C interactions, a three‐dimensional polymeric chain is created in the crystalline network. The density functional theory calculations at B3LYP, B3PW91, and M06 levels using the 6–31+G** basis set were in good agreement with the X‐ray crystallography data.

Journal

Heteroatom ChemistryWiley

Published: Sep 1, 2013

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