(±)-3-Bis(phenylsulfinyl)methyl-1,2-dimethylcyclopropene

Beckhaus, Hans‐Dieter; Kimura, Masahiro; Watson, William H.; Venier, Clifford G.; Kojić‐Prodić, Biserka

doi:10.1107/s0567740879011614

Cited by 6 publications

(4 citation statements)

References 1 publication

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“…The bond lengths and angles of (I) ( Table 1) show normal values (Allen et al, 1987). The S O, Csp 2 ÐS and Csp 3 ÐS bond lengths agree well with the corresponding values in previously reported -disulfoxide compounds (Beckhaus et al, 1979;Pelizzi, Coghi et al, 1976;. The bond angles at both the S atoms are in the range 98.0 (1)±107.3 (1) , which corresponds to tetrahedral geometry.…”

Section: Commentsupporting

confidence: 85%

meso-Bis(phenylsulfinyl)methane

2003

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The title compound, meso-C(13)H(12)O(2)S(2), is in an anti conformation, with R and S configurations around the S atoms. The two O atoms are trans to each other, and the same applies for the two benzene rings. The phenylsulfinyl groups are nearly orthogonal to the central dithiomethane group, and the orientation of the two phenyl rings are determined by the interactions in which they are involved. The packing is built from molecular columns stabilized by weak C-H...O interactions.

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Section: Commentsupporting

confidence: 85%

meso-Bis(phenylsulfinyl)methane

2003

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“…Also the S-C(ll) distance, 1.824(11), is longer than those reported for the S -C sp , (secondary) bond (1.802 -1.829 Ä: Svinning, Mo and Bruun, 1976;Tranqui et al, 1974;Carpy et al, 1979). The sulfoxide bond length, 1.490(4), is typical of values found for this bond: 1.484 -1.517 Ä (Hoyos- Guererro et al, 1983;Beckhaus et al, 1979;Svinning et al, 1976;de la Camp and Hope, 1970;Tranqui et al, 1974;Dahlen, 1974).…”

Section: Discussionmentioning

confidence: 72%

“…The S -C(l) bond, 1.806(6), is longer than other bonds of the S -C spI type (1.797 -1.804 Ä: Beckhaus et al, 1979;Dahlen, 1974;de la Camp and Hope, 1970). Also the S-C(ll) distance, 1.824(11), is longer than those reported for the S -C sp , (secondary) bond (1.802 -1.829 Ä: Svinning, Mo and Bruun, 1976;Tranqui et al, 1974;Carpy et al, 1979).…”

Section: Discussionmentioning

confidence: 99%

The crystal structure of p-nitrobenzyl ester of (+)-1,5-nitronaphthylsulfinylacetic acid

Kozioł¹,

Kurys²,

Janczewski³

1985

Zeitschrift Für Kristallographie - Crystalline Materials

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Absolute configuration / Crystal structure / (+)-l ^-Nitronaphthylsulfinylacetic acid esterAbstract. The crystal structure of CigH^^C^S has been determined by the single-crystal X-ray analysis. The crystals are monoclinic, space group P2\ [a = 12.429(2), b = 4.762(1), c = 15.689(2) Ä, β = 97.27(1)°, Ζ = 2, D c = 1.49, D m = 1.48 g cm' 3 , /i(CuΚα) = 1.86 mm" 1 ). The structure was refined to R = 0.0441 and R w = 0.0414 by full-matrix least-squares method using 1189 reflections. The absolute configuration at the sulphur atom was found to be R.

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“…However, the molecular and crystal structure has been determined by electron [28,29] and X-ray diffraction [30 333] for certain related compounds containing an arylsulfinyl fragment, such as diphenyl sulfoxide [28,30], (+)-methyl p-tolyl sulfoxide [31], (+)-3-bis(phenylsulfinyl)methyl-1,2-dimethylcyclopropene [32], and cis-2-ethoxy-1-phenylsulfinylcyclopropane [33]. The following bond lengths (A) were reported: C sp 23S 1.804 (6) [28,29], 1.76 (2) [30], 1.797 (6) [31], 1.791(5), 1.802 (5) [32], and 1.77 (2) [33]; S=O 1.489(5) [28,29], 1.47 (2) [30], 1.493(6) [31], 1.508(4), 1.487(4) [32], and 1.509 (8) [33]. The C sp 23S=O bond angle (deg) was reported to be 106.1(0.4) [30], 106.5(0.3) [31], and 105.1(4) [33].…”

mentioning

confidence: 99%

An ab initio Quantum-Chemical Study of C6H5S(O)CH3 and C6H5S(O)CF3

et al. 2005

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The potential functions of internal rotation around the C sp 23S bond in the C 6 H 5 S(O)CH 3 and C 6 H 5 S(O)CF 3 molecules were obtained by ab initio MP2(full)/6-31+G* calculations. The stationary points were identified by solving the vibrational problems. The structures in which the plane of the C sp 23S3C sp 3 bonds is approximately perpendicular to the benzene ring plane correspond to the energy minimum. The barriers to rotation around the C sp 23S bond, corrected for the zero-point vibration energy, are 21.29 [C 6 H 5 S(O)CH 3 ] and 28.98 [C 6 H 5 S(O)CF 3 ] kJ mol !1 . The bond angles (deg) are as follows: 95.7 (CSC), 107.1 (C sp 2SO), 106.3 (C sp 3SO) in C 6 H 5 S(O)CH 3 ; 93.5 (CSC), 108.2 (C sp 2SO), 105.2 (C sp 3SO) in C 6 H 5 S(O)CF 3 . The bond lengths are as follows (A): 1.520 (S=O), 1.804 (C sp 23S), 1.810 (C sp 33S) in C 6 H 5 S(O)CH 3 ; 1.507 (S=O), 1.799 (C sp 23S), 1.870 (C sp 33S) in C 6 H 5 S(O)CF 3 . According to the results of NBO calculations, the formally double S=O bond consists of a strongly polarized covalent s bond (S6O) and an almost ionic bond.An increase in the S=O bond multiplicity relative to a single bond is mainly due to hyperconjugation by the mechanism n(O)6s*(C sp 23S) and n(O)6s*(C sp 33S) and, to a lesser extent, by interaction of the oxygen lone electron pairs with the Rydberg orbitals of the S atoms, characterized by a large contribution of the d component.

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(±)-3-Bis(phenylsulfinyl)methyl-1,2-dimethylcyclopropene

Cited by 6 publications

References 1 publication

meso-Bis(phenylsulfinyl)methane

meso-Bis(phenylsulfinyl)methane

The crystal structure of p-nitrobenzyl ester of (+)-1,5-nitronaphthylsulfinylacetic acid

An ab initio Quantum-Chemical Study of C6H5S(O)CH3 and C6H5S(O)CF3

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