X-ray study of structure and charge density of 1-methylsulfonyl-2-phenylsulfonylethane

Mo, Frode; Gaasdal, A.

doi:10.1107/s0567740880008722

Cited by 5 publications

(6 citation statements)

References 49 publications

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“…-0.003 Ä. On the other hand the value of r(S -Me) from the high-0 refinement, 1.756(2) Ä , is in very good agreem ent with the values obtained by the same technique for two other methylsulphones, namely l,2-bis(m ethylsulphonyl)ethane, 1.755 -1.757(2) Ä [7], and l-methylsulphonyl-2-phenylsulphonylethane, 1.759(3) Ä [8].…”

Section: R Esu Lts and Discussionsupporting

confidence: 59%

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Molecular Structures of p-Methylsulphonylbenzoic Acid and Methylphenylsulphone: Comparison of X-Ray and Electron Diffraction Results

Brunvoll

Colapietro²,

Domenicano³

et al. 1984

Zeitschrift Für Naturforschung B

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The molecular structures of p-methylsulphonylbenzoic acid and methylphenylsulphone have been accurately determined by X-ray crystallography and gas electron diffraction, respectively. After correction for systematic effects, the geometry of the crystal molecule is seen to agree with that of the free molecule within a few thousandths of an Å unit for bond distances and a few tenths of a degree for bond angles. An exception is the S-Me bond distance, which is ca. 0.02 Å shorter in the crystal. The distortion of the benzene ring angles from 120°, an effect of the - SO2Me substituent, is virtually the same from both experiments

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Section: R Esu Lts and Discussionsupporting

confidence: 59%

“…The three hydrogen atoms of the -S 0 2Me substituent point towards sulphonyl oxy gens from neighbouring molecules, with C -H -O separations of 3.47-3.69 Ä. Short contacts between sulphonyl oxygens and aliphatic hydrogens are nor mal in crystalline sulphones [6][7][8].…”

Section: R Esu Lts and Discussionmentioning

confidence: 99%

Molecular Structures of p-Methylsulphonylbenzoic Acid and Methylphenylsulphone: Comparison of X-Ray and Electron Diffraction Results

Brunvoll

Colapietro²,

Domenicano³

et al. 1984

Zeitschrift Für Naturforschung B

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“…fia(£) -Rx(t) was approximated outside that window by an exponential decay function with a time constant of 10-20 ns, whose value was obtained by fitting to the latter part of the measured function. For the numerical Laplace transforms six frequencies per decade were used, spaced at equal intervals in log f. When benzene (x) was compared with cyclohexane (s) at 25 °C in five measurements, c'x -t's at 1, 10, and MHz was 0.258 (±0.013), 0.258 (±0.012), and 0.259 (±0.015), which compare well with the literature value31 of 0.251. Negligible loss values were obtained within that range, but at higher frequencies this was not so; moreover, the t' values there showed systematic errors and deteriorating precision.…”

Section: Mhzmentioning

confidence: 99%

“…As is shown in Figure 16, D±tX is sensitive to p, x, and a, tending to unity from above as x --1, with a slope that is steeper the greater the order in the chain (i.e., when a and p are both high). As a decreases towards 1/2, Dj_ x is less sensitive to x and becomes independent of p. The threshold parameter q was not introduced into this calculation, but if there is a threshold for the formation of a helix or a stiff section, Figure 17. Complex plane plot for a 5.00% (w/w) solution of X70X in benzene at 25 °C. The points are the mean of three separate measurements; the curve was obtained by least-squares fitting the data with eq 25, which found e'0 = 2.413, t'" = 2.316, = 22.7 ns, and ß = 0.495.…”

Section: Id-mentioning

confidence: 99%

Configurational order and kinetic flexibility in polysulfones studied at low and high frequencies by dielectric means using solutions of terpolymers of sulfur dioxide, hex-1-ene, and cyclohexene

Cole¹,

Winsor²,

Fawcett³

et al. 1987

Macromolecules

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A conformational analysis of poly(o1efin sulfone) chains emphasizing the role of third-order Markov correlations of bond conformation resulting from electrostatic interactions between adjacent sulfone dipoles on the main chain led us to prepare terpolymers of SO2, hex-1-ene, and cyclohexene and to study their dielectric behavior at low and high frequencies in dilute solution in order to measure the equilibrium dipole momenta that characterize the ordered structures. Chain stiffness, as measured by the magnitude of the low-frequency relaxing dipole moment, develops strongly in the terpolymers as the mole fraction of hex-1-ene sulfone residues nears unity and is interpreted by a model that falls between the random flight model and the wormlike chain model. Stiff polar segments are created by a sequence of gauche main-chain C-C bonds where the dipoles nest together in favorable electrostatic situations. The size and shape of these stiff segments cannot both be determined, but their configuration is probably close to that of a helix, and their mean content in poly(hex-1-ene sulfone) is about 20-25 atactic hex-1-ene residues. At high frequencies a new form of the time-domain system has found the relaxation time of the segmental relaxation discovered in these terpolymers not to be significantly reduced by the inclusion of a small proportion of cyclohexene sulfone residues, yet the poly(cyc1ohexene sulfone) chain itself is kinetically more flexible.

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“…The C(7) -0(3) bond, 1.367(2) Ä, is within the typical ränge for methoxybenzenes (Hauback et al, 1988;and references therein). The O -S-O angle, 117.8(1)°, is slightly larger than the corresponding mean value, 117.1[0.1]°^, for MSO2PS, l-(methylsulfonyl)-2-(phenylsulfonyl)ethane = MPSO2 (Mo and Gaasdal, 1980) and 1,2bis(methylsulfonyl)ethane = MMDS (Mo and Berg, 1982). All other angles in the fragment -CH2-SO2-CH3 in MSOzpmoPS, MSOjPS, MPSO2 and MMDS are in good agreement.…”

Section: Analyses Of Thermal Motionmentioning

confidence: 63%

Crystal structure of 1-(methylsulfonyl)- 2-(p-methoxyphenylthio)ethane at 87 K. A comparative study of two different crystals

Hauback¹,

Mo²

1990

Zeitschrift Für Kristallographie - Crystalline Materials

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The structure of l-(methylsulfonyl)-2-(p-methoxyphenylthio)ethane, C10H14O3S2, was determined from an X-ray diffraction study of two different crystals, A and B, at 87 K. The space group is monoclinic, Pljc, a = 10.859(1), b = 5.310(1), c = 19.934 (3) 98.49(2)° and Z = 4 from high-order reflections for crystal B. Intensities were collected to (sin 0)ß = 0.650 for crystal A and to 0.904 Ä"' for B with MoÄa radiation. The structure was solved by direct methods. Parameters derived for crystal A (Ä = 0.029 for 2418 FJ and from the data with (sin0)/ X < 0.650 Ä"' for B (Ä = 0.032 for 2402 F,) were compared and analysed by half-normal probability plots and by x^ tests. The agreement is very good. The slopes in all plots are < 1.0 indicating a slight overestimation of the Standard deviates. A normal probability plot of the two sets of observed F^ [(sin 9)/X < 0.65 Ä~'] has a siope very dose to 1.0. Least-squares refmements have been carried out with various subsets of data for crystal B. The Parameters from the refmement with (sin 0)/A > 0.75 Ä"' were taken to give the best description of the structure (/? = 0.027, 1387 F"). The refined bond lengths in the fragment containing S and the phenyl ring were corrected for thermal motion. Before correction the ring C -C bonds are about 0.0034 Ä longer than the values from the refinement with all data. Bonding Parameters at the S atoms corroborate previous observations for some closely related sulfide and sulfone structures. The distortions from €2« symmetry in the para-substituted phenyl ring is largely effected by the OCH 3 group which is confirmed from a comparison of various parasubstituted anisoles. The observed reversible change in colour of the crystals, from colourless at room temperature to pale purple at 87 K seems to be related to a shortening of an intermolecular S • • • Ph contact.

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X-ray study of structure and charge density of 1-methylsulfonyl-2-phenylsulfonylethane

Cited by 5 publications

References 49 publications

Molecular Structures of p-Methylsulphonylbenzoic Acid and Methylphenylsulphone: Comparison of X-Ray and Electron Diffraction Results

Molecular Structures of p-Methylsulphonylbenzoic Acid and Methylphenylsulphone: Comparison of X-Ray and Electron Diffraction Results

Configurational order and kinetic flexibility in polysulfones studied at low and high frequencies by dielectric means using solutions of terpolymers of sulfur dioxide, hex-1-ene, and cyclohexene

Crystal structure of 1-(methylsulfonyl)- 2-(p-methoxyphenylthio)ethane at 87 K. A comparative study of two different crystals

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