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Chemphyschem. 2016 May 18;17(10):1463-7. doi: 10.1002/cphc.201600063. Epub 2016 Mar 10.

Structures of Trichloromethyl Thiocyanate, CCl3 SCN, in Gaseous and Crystalline State.

Author information

1
CEQUINOR (CONICET-UNLP), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 esq. 115, 1900, La Plata, Argentina.
2
Strukturchemie, Institut für Anorganische Chemie, Universität Duisburg Essen, Universitätsstraße 7, 45117, Essen, Germany.
3
Lehrstuhl für Anorganische Chemie und Strukturchemie, Centre for Molecular Materials CM2, Universität Bielefeld, Universitätsstraße 25, 33615, Bielefeld, Germany.
4
Lehrstuhl für Anorganische Chemie und Strukturchemie, Centre for Molecular Materials CM2, Universität Bielefeld, Universitätsstraße 25, 33615, Bielefeld, Germany. mitzel@uni-bielefeld.de.
5
CEQUINOR (CONICET-UNLP), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 esq. 115, 1900, La Plata, Argentina. carlosdv@quimica.unlp.edu.ar.

Abstract

Trichloromethyl thiocyanate, CCl3 SCN, was structurally studied in both the gas and crystal phases by means of gas electron diffraction (GED) and single-crystal X-ray diffraction (XRD), respectively. Both experimental studies and quantum chemical calculations indicate a staggered orientation of the CCl3 group relative to the SCN group. This conclusion is supported by the similarity of the C-SCN bond length to that of the anti-structure of CH2 ClSCN (Berrueta Martínez et al. Phys. Chem. Chem. Phys. 2015, 17, 15805-15812). Bond lengths and angles are similar for gas and crystal CCl3 SCN structures; however, the crystal structure presents different intermolecular interactions. These include halogen and chalcogen type interactions, the geometry of which was studied. Characteristic C-Y⋅⋅⋅N angles (Y=Cl or S) close to 180° provide evidence for typical σ-hole interactions along the halogen/chalcogen-carbon bond in N⋅⋅⋅Cl and N⋅⋅⋅S, intermolecular units.

KEYWORDS:

chalcogens; conformation analysis; density functional calculations; halogens; solid-state structures

PMID:
26865044
DOI:
10.1002/cphc.201600063

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