2003
DOI: 10.1021/ic030058p
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Structure and Conformations of N-(Fluoroformyl)imidosulfurous Dichloride, FC(O)NSCl2

Abstract: The IR (gas) and Raman (liquid) spectra of FC(O)NSCl(2) demonstrate the presence of a conformational mixture in both phases. According to a gas electron diffraction study, the main conformer (94(8)%) possesses a syn-syn structure (C(O)F group synperiplanar with respect to the SCl(2) bisector and the C=O bond synperiplanar to the N=S bond). Quantum chemical calculations (HF, B3LYP and MP2 with 6-31G basis set, and MP2/6-311(2df)) predict a syn-anti structure for the second conformer. Analysis of the IR (gas) sp… Show more

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Cited by 14 publications
(10 citation statements)
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“…The vibrational spectra can be interpreted satisfactorily on the basis of the presence of only one form. Assignment of the bands related to the N=SCl 2 moiety was performed on the basis of the corresponding features for similar S , S ‐dichlorosulfur imide derivatives such as CF 3 N=SCl 2 ,23 FC(O)N=SCl 2 ,25 and ClSO 2 N=SCl 2 31. The corresponding S , S ‐difluoro derivatives CF 3 N=SF 2 ,32 FC(O)N=SF 2 ,23 and ClSO 2 N=SF 2 22 were also taken into account to establish a correlation between the different modes.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The vibrational spectra can be interpreted satisfactorily on the basis of the presence of only one form. Assignment of the bands related to the N=SCl 2 moiety was performed on the basis of the corresponding features for similar S , S ‐dichlorosulfur imide derivatives such as CF 3 N=SCl 2 ,23 FC(O)N=SCl 2 ,25 and ClSO 2 N=SCl 2 31. The corresponding S , S ‐difluoro derivatives CF 3 N=SF 2 ,32 FC(O)N=SF 2 ,23 and ClSO 2 N=SF 2 22 were also taken into account to establish a correlation between the different modes.…”
Section: Resultsmentioning
confidence: 99%
“…Vibrational spectroscopy, gas electron diffraction, X‐ray crystallography, quantum chemical calculations, and other techniques have proved to be powerful tools to understand the structural properties of sulfur imide molecules containing fluorine atoms or fluorinated substituents groups. Thus, the structure and conformational and configurational properties of molecules of the type R F N=SF 2 [R F = CF 3 ,1316 FC(O),17,18 NC,19 CF 3 C(O),20 and FSO 2 21,22] and R F N=SCl 2 [R F = CF 3 23,24 and FC(O)25] have been studied, all of which show only a ( Z ) configuration around the putative N=S double bond. It is interesting to note that compounds with different substituents attached at the sulfur atom of the N=S group favor the ( E ) form.…”
Section: Introductionmentioning
confidence: 99%
“…The results will be compared with related species (OSF 2 , O 2 SF 2 , HNS(O)F 2 , ClNS VI (O)F 2 , NCNS(O)F 2 , FC(O)NSF 2 , and FC(O)NS(F)CF 3 6 ) sequenced by using the Lewis formalism. This comparison also includes related previously reported compounds CF 3 C(O)NS(F)CF 3 and FC(O)NSCl 2 …”
Section: Introductionmentioning
confidence: 83%
“…In fact, so far the only reported compound with a single N-S bond and S(+2) is CF 3 -S-NF 2 [1], whereas several S(+6)-compounds such NBBSF 2 -N5 5SF 2 and NBBSF 2 -N5 5S(O)F 2 , possessing not only a single, but also a triple sulfur-nitrogen bond, have recently been prepared and characterized [2]. In contrast, plenty stable S(+4) compounds with N5 5S double bond have been studied so far, for example molecules of the type R-N5 5SX 2 (CF 3 N5 5SF 2 [3], CF 3 N5 5SCl 2 [4], FC(O)N5 5SF 2 [5], FC(O)N5 5SCl 2 [6], C 2 F 5 N5 5SF 2 [7], C 2 F 5 N5 5SCl 2 [8] and CH 3 N5 5S(CF 3 ) 2 [9]) and RN5 5S5 5O (CF 3 -N5 5S5 5O and SF 5 N5 5S5 5O [10]). However, those which have attracted our present interest are the S(+4)-compounds with single N-S bonds, particularly a substance containing the entity N-SF 3 , in account of its influence on the reactivity and the conformational properties.…”
Section: Introductionmentioning
confidence: 99%