Dichlorophosphanyl isocyanate - spectroscopy, conformation and molecular structure in the gas phase and the solid state

Li D, Schwabedissen J, Stammler H-G, Mitzel NW, Willner H, Zeng X (2016)
PHYSICAL CHEMISTRY CHEMICAL PHYSICS 18(37): 26245-26253.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Autor
; ; ; ; ;
Abstract / Bemerkung
Dichlorophosphanyl isocyanate, Cl2PNCO, was synthesized and characterized by IR, Raman and P-31 NMR spectroscopy. The conformational properties and molecular structures were studied by using gas electron diffraction (GED), X-ray crystallography and quantum-chemical calculations. Extensive DFT and ab initio calculations show that the potential energy surface of Cl2PNCO upon rotating the P-N bond is rather flat; three conformers, namely syn, anti and gauche between the NCO group and the bisector of the ClPCl angle, were theoretically predicted. Experimentally, only one conformer was indicated by gas-phase IR spectroscopy and the preference for a gauche conformation in both gas phase and solid state was unambiguously ascertained by gas electron diffraction and X-ray crystallographic data. In the solid state, the Cl2PNCO molecules adopt a gauche conformation with two distinct dihedral angles Cl-P-N-C of -121.3(2) and 137.4(2)degrees and form polymeric chains through weak intermolecular C center dot center dot center dot O contacts. Additionally, the dynamic character of the position of the isocyanate group of Cl2PNCO was examined in the gas phase.
Erscheinungsjahr
Zeitschriftentitel
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Band
18
Ausgabe
37
Seite(n)
26245-26253
ISSN
eISSN
PUB-ID

Zitieren

Li D, Schwabedissen J, Stammler H-G, Mitzel NW, Willner H, Zeng X. Dichlorophosphanyl isocyanate - spectroscopy, conformation and molecular structure in the gas phase and the solid state. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 2016;18(37):26245-26253.
Li, D., Schwabedissen, J., Stammler, H. - G., Mitzel, N. W., Willner, H., & Zeng, X. (2016). Dichlorophosphanyl isocyanate - spectroscopy, conformation and molecular structure in the gas phase and the solid state. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 18(37), 26245-26253. doi:10.1039/c6cp05377g
Li, D., Schwabedissen, J., Stammler, H. - G., Mitzel, N. W., Willner, H., and Zeng, X. (2016). Dichlorophosphanyl isocyanate - spectroscopy, conformation and molecular structure in the gas phase and the solid state. PHYSICAL CHEMISTRY CHEMICAL PHYSICS 18, 26245-26253.
Li, D., et al., 2016. Dichlorophosphanyl isocyanate - spectroscopy, conformation and molecular structure in the gas phase and the solid state. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 18(37), p 26245-26253.
D. Li, et al., “Dichlorophosphanyl isocyanate - spectroscopy, conformation and molecular structure in the gas phase and the solid state”, PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 18, 2016, pp. 26245-26253.
Li, D., Schwabedissen, J., Stammler, H.-G., Mitzel, N.W., Willner, H., Zeng, X.: Dichlorophosphanyl isocyanate - spectroscopy, conformation and molecular structure in the gas phase and the solid state. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 18, 26245-26253 (2016).
Li, Dingqing, Schwabedissen, Jan, Stammler, Hans-Georg, Mitzel, Norbert W., Willner, Helge, and Zeng, Xiaoqing. “Dichlorophosphanyl isocyanate - spectroscopy, conformation and molecular structure in the gas phase and the solid state”. PHYSICAL CHEMISTRY CHEMICAL PHYSICS 18.37 (2016): 26245-26253.

59 References

Daten bereitgestellt von Europe PubMed Central.

On the versatility of urethane/urea bonds: reversibility, blocked isocyanate, and non-isocyanate polyurethane.
Delebecq E, Pascault JP, Boutevin B, Ganachaud F., Chem. Rev. 113(1), 2012
PMID: 23082894

Ozaki, Chem. Rev. 72(), 1972
Reactive N-protonated isocyanate species stabilized by bis(μ-hydroxo)divanadium(IV)-substituted polyoxometalate.
Uehara K, Fukaya K, Mizuno N., Angew. Chem. Int. Ed. Engl. 51(31), 2012
PMID: 22736381
Facile synthesis of sterically hindered and electron-deficient secondary amides from isocyanates.
Schafer G, Matthey C, Bode JW., Angew. Chem. Int. Ed. Engl. 51(36), 2012
PMID: 22890627

Durig, J. Am. Chem. Soc. 110(), 1988
Chlorodifluoroacetyl isocyanate, ClF2CC(O)NCO: preparation and structural and spectroscopic studies.
Ramos LA, Ulic SE, Romano RM, Vishnevskiy YV, Berger RJ, Mitzel NW, Beckers H, Willner H, Tong S, Ge M, Della Vedova CO., J Phys Chem A 116(47), 2012
PMID: 23116327
Conformational and structural determination of F(2)NC(O)F and F(2)NC(O)NCO. A joint experimental and theoretical study.
Erben MF, Padro JM, Willner H, Della Vedova CO., J Phys Chem A 113(46), 2009
PMID: 19807144
Molecular Structure of Cyclopropyl (Isocyanato) Silane: A Combined Microwave Spectral and Theoretical Study.
Guirgis GA, Askarian SM, Morris T, Palmer MH, Pate BH, Seifert NA., J Phys Chem A 119(49), 2015
PMID: 26580291
The molecular structure of methylfluoroisocyanato silane: a combined microwave spectral and theoretical study.
Guirgis GA, Overby JS, Barker TJ, Palmer MH, Pate BH, Seifert NA., J Phys Chem A 119(4), 2015
PMID: 25551546
Preparation and properties of methoxycarbonylsulfenyl isocyanate, CH(3)OC(O)SNCO.
Vallejos ST, Erben MF, Willner H, Boese R, Vedova CO., J. Org. Chem. 72(24), 2007
PMID: 17963404
Photofragmentation Mechanisms of Chlorosulfonyl Isocyanate, ClSO2NCO, Excited with Synchrotron Radiation between 12 and 550 eV.
Moreno Betancourt A, Bava YB, Berrueta Martinez Y, Erben MF, Cavasso Filho RL, Della Vedova CO, Romano RM., J Phys Chem A 119(29), 2015
PMID: 26121558
Electronic properties of fluorosulfonyl isocyanate, FSO2NCO: a photoelectron spectroscopy and synchrotron photoionization study.
Moreno Betancourt A, Flores Antognini A, Erben MF, Cavasso-Filho R, Tong S, Ge M, Della Vedova CO, Romano RM., J Phys Chem A 117(38), 2013
PMID: 23977899
All the 2p-block elements in a molecule: experimental and theoretical studies of FBNCO and FBNCO⁺.
Troiani A, Garzoli S, Pepi F, Ricci A, Rosi M, Salvitti C, de Petris G., Chem. Commun. (Camb.) 50(90), 2014
PMID: 25266166

Hausser, Inorg. Chem. 29(), 1990

Liu, J. Polym. Sci., Part A: Polym. Chem. 35(), 1997

Samaraj, Angew. Chem., Int. Ed. 7(), 1968
Phosphorus isocyanates.
Derkatsch GI., Angew. Chem. Int. Ed. Engl. 8(6), 1969
PMID: 4979646

Rankin, J. Chem. Soc., Dalton Trans. (), 1981

Zeng, Eur. J. Inorg. Chem. (), 2011

Anderson, J. Am. Chem. Soc. 67(), 1945

Fluck, Z. Anorg. Allg. Chem. 338(), 1965

Egorov, J. Struct. Chem. 14(), 1973

Berger, Z. Naturforsch. 64B(), 2009

Reuter, Z. Naturforsch. 71B(), 2016

Vishnevskiy, J. Mol. Struct. 833(), 2007

Vishnevskiy, J. Mol. Struct. 871(), 2007

AUTHOR UNKNOWN, 0

Vishnevskiy, J. Mol. Struct. 833(), 2007

Sipachev, THEOCHEM 22(), 1985

Sipachev, J. Mol. Struct. 567(), 2001

Sipachev, J. Mol. Struct. 693(), 2004

Sipachev, Struct. Chem. 11(), 2000

Dolomanov, J. Appl. Crystallogr. 42(), 2009

Palatinus, J. Appl. Crystallogr. 40(), 2007
A short history of SHELX.
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677

Becke, J. Chem. Phys. 98(), 1993
Atoms, molecules, solids, and surfaces: Applications of the generalized gradient approximation for exchange and correlation.
Perdew JP, Chevary JA, Vosko SH, Jackson KA, Pederson MR, Singh DJ, Fiolhais C., Phys. Rev., B Condens. Matter 46(11), 1992
PMID: 10002368

Perdew, Phys. Rev. Lett. 78(), 1997

Zhao, Theor. Chem. Acc. 120(), 2008

Roothaan, Rev. Mod. Phys. 23(), 1951

Møller, Phys. Rev. 46(), 1934

Gillespie, 1991
Models of molecular geometry.
Gillespie RJ, Robinson EA., Chem Soc Rev 34(5), 2005
PMID: 15852152

Miller, Spectrochim. Acta 18(), 1962

Hartl, Z. Naturforsch. 34B(), 1979

Bent, Chem. Rev. 61(), 1961

Shelly, Inorg. Chem. 31(), 1992

Barrow, J. Chem. Soc., Dalton Trans. (), 1980

Bondi, J. Phys. Chem. 68(), 1964
Synthesis and characterization of 1,2,3,4,5-pentafluoroferrocene.
Sunkel K, Weigand S, Hoffmann A, Blomeyer S, Reuter CG, Vishnevskiy YV, Mitzel NW., J. Am. Chem. Soc. 137(1), 2014
PMID: 25531826
Chlorodifluoroacetyl cyanide, ClF2CC(O)CN: synthesis, structure, and spectroscopic characterization.
Ramos LA, Ulic SE, Romano RM, Tong S, Ge M, Vishnevskiy YV, Berger RJ, Mitzel NW, Beckers H, Willner H, Della Vedova CO., Inorg Chem 50(19), 2011
PMID: 21870792

Hilderbrandt, J. Mol. Struct. 3(), 1969

Airey, J. Mol. Struct. 8(), 1971

Gobbato, Chem. Phys. Lett. 266(), 1997

Brunvoll, J. Chem. Soc., Dalton Trans. (), 1978

Della, J. Mol. Struct. 380(), 1996
Carbonyl Diisocyanate CO(NCO)2: Synthesis and Structures in Solid State and Gas Phase.
Klapotke TM, Krumm B, Rest S, Scharf R, Schwabedissen J, Stammler HG, Mitzel NW., J Phys Chem A 120(26), 2016
PMID: 27341337

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 27711553
PubMed | Europe PMC

Suchen in

Google Scholar