Determination of the molecular structure of sulfonyl chloride isocyanate using microwave spectroscopy

Jo, O. L.; Graybeal, Jack D.; Lovas, Francis J.; Suenram, R. D.

doi:10.1016/0022-2852(92)90067-x

Cited by 24 publications

(4 citation statements)

References 35 publications

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“…This turned our attention to investigate another interesting series, halosulfonyl azides XSO2-NNN (X is F and Cl) in a previous work [13]. From energy optimizations and calculated potential scans fluoro-and chlorosulfonyl azides were predicted to exist only as the gauche conformation similar to the corresponding isocyanates XSO2-NCO [1][2][3][4][5][6]. An identical result we find in the present study on haloselenonyl azides with X being F, Cl and Br.…”

Section: Introductionsupporting

confidence: 70%

“…The conformational behavior of fluorosulfonyl isocyanate F-SO2-NCO and chlorosulfonyl isocyanate Cl-SO2-NCO has drawn the attention of structural chemists and spectroscopists because of their interesting structure and importance in chemistry [1][2][3][4][5][6]. They have been investigated over the past few years by both theoretical and spectroscopic methods.…”

Section: Introductionmentioning

confidence: 99%

“…Second, the substance was described as one form having a rotation angle of 86 o and a large amplitude of rotation around the S-N bond [1]. Microwave studies on the same molecule indicated that the Cl-S-N=C dihedral angle is 94 o and that the NCO group is not linear for the lowest energy conformer [2]. A later ab initio study predicted a single gauche conformation with a Cl-S-N=C dihedral angle of 104.8 o [3].…”

Section: Introductionmentioning

confidence: 99%

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Structural Stability and Vibrational Analyses of Haloselenonyl Azides, XSeO2-NNN, where X is F, Cl, Br

Förner

Badawi

Seddigi

2005

IJMS

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Abstract:The structural stability of haloselenonyl azides was investigated by quantum mechanical Møller-Plesset perturbation theory of second order and density functional theory calculations. The 6-311+G** basis set was used to include polarization and diffuse functions in the calculations at the DFT-B3LYP level. The potential scans for the rotation of the -NNN rotor were calculated and found to be consistent with a single minimum that corresponds to a gauche conformation (-NNN moiety nearly eclipses one of the two selenonyl Se=O bonds) for the three halogens at ambient temperature. The structural parameters for the minima calculated by MP2 and DFT turned out to be very similar. The vibrational modes, infrared and Raman intensities as well as depolarization ratios were calculated at DFT-B3LYP/6-311+G** level for the three molecules in their gauche conformations. The potential energy distributions among symmetry coordinates of the normal modes of the molecules in their gauche conformation were then computed from normal coordinate analyses.

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Section: Introductionsupporting

confidence: 70%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Structural Stability and Vibrational Analyses of Haloselenonyl Azides, XSeO2-NNN, where X is F, Cl, Br

Förner

Badawi

Seddigi

2005

IJMS

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“…On the other hand, a GED study suggested the existence of a second conformer c for ClSO 2 NCO beside conformation b . However, more recent computational and vibrational studies of the gas, liquid, and solid phases did not find any evidence for the existence of a second conformer beside the dominant conformer b …”

Section: Introductionmentioning

confidence: 96%

Anomeric Effects in Sulfonyl Compounds: An Experimental and Computational Study of Fluorosulfonyl Azide, FSO₂N₃, and Trifluoromethylsulfonyl Azide, CF₃SO₂N₃

et al. 2010

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Fluorosulfonyl azide, FSO(2)N(3), was characterized by IR (gas phase, Ar matrix), and Raman (liquid) spectroscopy. According to the matrix IR spectrum of (18)O-labeled FSO(2)N(3), its two oxygen atoms are nonequivalent. This assumption was confirmed by the X-ray crystal structure of FSO(2)N(3) at -123 degrees C, as only one conformer was observed with one of the S=O bonds in synperiplanar position to the N(3) group (phi(OS-NN) = -14.8(3) degrees) with respect to the S-N bond. The same conformation was found for trifluoromethylsulfonyl azide, CF(3)SO(2)N(3) (phi(OS-NN) = -23.74(15) degrees), in the solid state. The preference of such a synperiplanar configuration between S=O and N(3) was rationalized by a predominant anomeric interaction of n(sigma)(N) --> sigma*(S-O), as supported by the experiment and quantum chemical calculations.

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ChemInform Abstract: Determination of the Molecular Structure of Sulfonyl Chloride Isocyanate Using Microwave Spectroscopy.

Graybeal

Lovas

et al. 1992

ChemInform

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Determination of the molecular structure of sulfonyl chloride isocyanate using microwave spectroscopy

Cited by 24 publications

References 35 publications

Structural Stability and Vibrational Analyses of Haloselenonyl Azides, XSeO2-NNN, where X is F, Cl, Br

Structural Stability and Vibrational Analyses of Haloselenonyl Azides, XSeO2-NNN, where X is F, Cl, Br

Anomeric Effects in Sulfonyl Compounds: An Experimental and Computational Study of Fluorosulfonyl Azide, FSO₂N₃, and Trifluoromethylsulfonyl Azide, CF₃SO₂N₃

ChemInform Abstract: Determination of the Molecular Structure of Sulfonyl Chloride Isocyanate Using Microwave Spectroscopy.

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Determination of the molecular structure of sulfonyl chloride isocyanate using microwave spectroscopy

Cited by 24 publications

References 35 publications

Structural Stability and Vibrational Analyses of Haloselenonyl Azides, XSeO2-NNN, where X is F, Cl, Br

Structural Stability and Vibrational Analyses of Haloselenonyl Azides, XSeO2-NNN, where X is F, Cl, Br

Anomeric Effects in Sulfonyl Compounds: An Experimental and Computational Study of Fluorosulfonyl Azide, FSO2N3, and Trifluoromethylsulfonyl Azide, CF3SO2N3

ChemInform Abstract: Determination of the Molecular Structure of Sulfonyl Chloride Isocyanate Using Microwave Spectroscopy.

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Anomeric Effects in Sulfonyl Compounds: An Experimental and Computational Study of Fluorosulfonyl Azide, FSO₂N₃, and Trifluoromethylsulfonyl Azide, CF₃SO₂N₃