Conformational Properties of Ethyl- and 2,2,2-Trifluoroethyl Thionitrites, (CX3CH2SNO, X = H and F)

Canneva A, Della Vedova CO, Mitzel NW, Erben MF (2015)
The Journal of Physical Chemistry A 119(9): 1524-1533.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
The simple 2,2,2-trifluoroethyl thionitrite molecule, CF3CH2SNO, has been prepared in good yield for the first time using CF3CH2SH and NOCl in slight excess. The vapor pressure of the red-brown compound CF3CH2SNO follows, in the temperature range between 226 and 268 K, the equation log p = 12.0-3881/T (p/bar, T/K), and its extrapolated boiling point reaches 51 degrees C. Its structural and conformational properties have been compared with the ethyl thionitrite analogue, CH3CH2SNO. The FTIR spectra of the vapor of both thionitrites show the presence of bands with well-defined contours, allowing for a detailed conformational analysis and vibrational assignment on the basis of a normal coordinate analysis. The conformational space of both thionitrite derivatives has also been studied by using the DFT and MP2(full) level of theory with extended basis sets [6-311+G(2df) and cc-pVTZ]. The overall evaluation of the experimental and theoretical results suggests the existence of a mixture of two conformers at room temperature. The relative abundance of the most stable syn form (N=O double bond syn with respect to the C-S single bond) has been estimated to be ca. 79 and 75% for CF3CH2SNO and CH3CH2SNO, respectively.
Erscheinungsjahr
2015
Zeitschriftentitel
The Journal of Physical Chemistry A
Band
119
Ausgabe
9
Seite(n)
1524-1533
ISSN
1089-5639
Page URI
https://pub.uni-bielefeld.de/record/2731059

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Canneva A, Della Vedova CO, Mitzel NW, Erben MF. Conformational Properties of Ethyl- and 2,2,2-Trifluoroethyl Thionitrites, (CX3CH2SNO, X = H and F). The Journal of Physical Chemistry A. 2015;119(9):1524-1533.
Canneva, A., Della Vedova, C. O., Mitzel, N. W., & Erben, M. F. (2015). Conformational Properties of Ethyl- and 2,2,2-Trifluoroethyl Thionitrites, (CX3CH2SNO, X = H and F). The Journal of Physical Chemistry A, 119(9), 1524-1533. doi:10.1021/jp507406w
Canneva, A., Della Vedova, C. O., Mitzel, N. W., and Erben, M. F. (2015). Conformational Properties of Ethyl- and 2,2,2-Trifluoroethyl Thionitrites, (CX3CH2SNO, X = H and F). The Journal of Physical Chemistry A 119, 1524-1533.
Canneva, A., et al., 2015. Conformational Properties of Ethyl- and 2,2,2-Trifluoroethyl Thionitrites, (CX3CH2SNO, X = H and F). The Journal of Physical Chemistry A, 119(9), p 1524-1533.
A. Canneva, et al., “Conformational Properties of Ethyl- and 2,2,2-Trifluoroethyl Thionitrites, (CX3CH2SNO, X = H and F)”, The Journal of Physical Chemistry A, vol. 119, 2015, pp. 1524-1533.
Canneva, A., Della Vedova, C.O., Mitzel, N.W., Erben, M.F.: Conformational Properties of Ethyl- and 2,2,2-Trifluoroethyl Thionitrites, (CX3CH2SNO, X = H and F). The Journal of Physical Chemistry A. 119, 1524-1533 (2015).
Canneva, Antonela, Della Vedova, Carlos O., Mitzel, Norbert W., and Erben, Mauricio F. “Conformational Properties of Ethyl- and 2,2,2-Trifluoroethyl Thionitrites, (CX3CH2SNO, X = H and F)”. The Journal of Physical Chemistry A 119.9 (2015): 1524-1533.

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