Crystal structure of S-p-nitrophenyl-5-phenyl- S-fluorothiazyne, (C6H5)NFS(C6H4NO2)

Horn, Ernst; Dong, Tungalag; Fujii, Takayoshi; Yoshimura, Toshiaki; Shimasaki, Choichiro

doi:10.1515/ncrs-2000-0325

Zeitschrift Für Kristallographie - New Crystal Structures

2000

DOI: 10.1515/ncrs-2000-0325

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Crystal structure of S-p-nitrophenyl-5-phenyl- S-fluorothiazyne, (C6H5)NFS(C6H4NO2)

Ernst Horn

Tungalag Dong

Takayoshi Fujii

et al.

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“…5 has an S-shaped C s structure. The S(1)−N(1) bond length in 5 is 1.457(2) Å, which is very close to the SN triple bond length [1.435(2)−1.462 Å] of λ 6 -sulfanenitriles. , The bridgings S(1)−N(2) and S(2)−N(2) bond lengths are 1.656(2) and 1.550(2) Å, respectively. These values lie between those of single and double bonds and are close to those of 3 and 4 .…”

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confidence: 53%

Synthesis and Properties of Ph₂S(N(Ph₂)S⋮N)₂

et al. 2005

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A new type of lambda6-sulfanenitrile with an SN triple bond at both ends, Ph2S(=N-(Ph2)S[triple bond]N)2 (5), was prepared in excellent yield from the one-pot synthesis of diphenylsulfimide (Ph2SNH) with fluoro(diphenyl)-lambda6-sulfanenitrile (Ph2FSN) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. Its molecular structure was determined by X-ray crystallographic analysis. Compound 5 reacted further with methyl triflate and trifluoromethanesulfonic anhydride to afford the corresponding bis-N-methylated and -N-sulfonated compounds.

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confidence: 53%

Synthesis and Properties of Ph₂S(N(Ph₂)S⋮N)₂

et al. 2005

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Electronic Structure of Sulfanenitriles

Bharatam¹,

Amita²,

Senthil³

2003

Bulletin of the Chemical Society of Japan

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Ab initio calculations have been carried out to analyze the electronic structure of organosulfur compounds with S≡N. The electronic structures of R3S≡N, R(O)S≡N, and RS≡N have been compared. The calculations suggest that the S–N interactions should be taken as a hybrid of the S≡N triple bond and the S+–N− single bond. The balance between the two resonating structures shift towards a S≡N triple-bonded arrangement with an increase in the electronegativity of substituents on sulfur. The strength of the Lewis basicity of sulfanenitriles has been estimated by studying their proton affinities and the complexation energies with BH3. On the potential energy surface of H3S≡N, this hypervalent compound has been shown to be a high-energy local minimum; although its 1,2-H shift isomers are all more stable, the barrier for the 1,2-shift is very high.

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Crystal structure of S-p-nitrophenyl-5-phenyl- S-fluorothiazyne, (C6H5)NFS(C6H4NO2)

Cited by 2 publications

References 2 publications

Synthesis and Properties of Ph₂S(N(Ph₂)S⋮N)₂

Synthesis and Properties of Ph₂S(N(Ph₂)S⋮N)₂

Electronic Structure of Sulfanenitriles

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Crystal structure of S-p-nitrophenyl-5-phenyl- S-fluorothiazyne, (C6H5)NFS(C6H4NO2)

Cited by 2 publications

References 2 publications

Synthesis and Properties of Ph2S(N(Ph2)S⋮N)2

Synthesis and Properties of Ph2S(N(Ph2)S⋮N)2

Electronic Structure of Sulfanenitriles

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Synthesis and Properties of Ph₂S(N(Ph₂)S⋮N)₂

Synthesis and Properties of Ph₂S(N(Ph₂)S⋮N)₂