Bond-length/Dihedral-angle and Bond-length/Bond-order Relationships for Sulphur(II)-Sulphur(II) Bonds.

Hordvik, Asbjørn; Grjotheim, K.; Krohn, Christine E.; Motzfeldt, K.; Williams, D. H.; Bunnenberg, E.; Djerassi, Carl; Records, Ruth

doi:10.3891/acta.chem.scand.20-1885

Cited by 115 publications

(41 citation statements)

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“…-a]-s-t riazi ne 2,4,5-Trichloro-6-(methylthio)isophthalonitrile 3,3'-Trithiobis-(2,4-pentanedione) 2,2'-Dithiobis-(l-phenyl-l,3-butanedione) 3,3'-Dithiobis-(2,4-pentanedione) Power & Jones (1971c) This study The S(1)-S(2) distance of 2.082 (2) A is slightly longer than that anticipated from the plot of S-S bond length versus the -C-S-S-C-torsion angle (Hordvik, 1966). The torsion angle in this study is 68.6 °.…”

Section: Discussionmentioning

confidence: 78%

The crystal and molecular structure of the enol form of 3,3'-dithiobis-(2,4-pentanedione)

Jones¹,

Power²

1976

Acta Crystallogr Sect B

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The crystal structure of the enol form of 3,3'-dithiobis-(2,4-pentanedione), C10H~404S2, has been determined using three-dimensional X-ray diffraction data (Mo K0c radiation) collected by counter methods.A report [Power & Jones, Inorg. Nucl. Chem. Lett. (1971), 7, 887-890] outlining what is now known to be the incorrect structure, has previously been published. The compound crystallizes in the orthorhombic space group Pna21 and has cell dimensions a= 14-852 (5), b= 12.264 (4) and c=6.935 (2) A; at,,= 1.36, de= 1-38 g cm -a for Z=4. The structure was refined, on F, by full-matrix, least-squares methods to an R value of 0.053 and wR of 0.038 for 1297 measured reflexions. The molecule exists as the enol tautomer and the short, intramolecular hydrogen bonds formed [O..-O contacts of 2.418 (6) and 2.444 (7) A] are asymmetric. There is evidence for alternating single and double bonds in the enol ring. The S-S distance is 2.082 (2) A and the C-S distances are 1.744 (5) and 1-743 (4) ~. From comparison with other organic sulphides, a dependence of the C-S bond length on the state of hybridization of the carbon atom is indicated. The C-S-S-C torsion angle is 68-6 °.

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Section: Discussionmentioning

confidence: 78%

The crystal and molecular structure of the enol form of 3,3'-dithiobis-(2,4-pentanedione)

Jones¹,

Power²

1976

Acta Crystallogr Sect B

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“…Perhaps more significant is that the Te-Te-Te-Te dihedral angle of 99.9 (1) ° in the Ph4 P+ structure is considerably smaller than the present value of 105.3 (1) °. As noted by Hordvik (1966) there is a correlation between disulfide bond lengths and dihedral angles (presumably due to eclipsing of lone pairs on the chalogen atoms involved) and this may be responsible for the longer bond lengths in the Ph4 P÷ salt. Unfortunately the dihedral angles in the Te 2-salt are not readily available.…”

mentioning

confidence: 99%

(4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)sodium tetratelluride(2-)

Devereux¹,

Schrobilgen²,

Sawyer³

1985

Acta Crystallogr C

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“…This bond length differs significantly from those usually found in aliphatic disulfides with dihedral angles near to 90 ° (Hordvik, 1966;Lee, 1972;Lee & Bryant, 1970;Lee & Bryant, 1969aOttersen, Warner & Serf, 1973b). The sulfur-sulfur bond lengths reported for dicinnamyl disulfide (lee & Bryant, 1971) and dibenzyl disulfide (Lee & Bryant, 1969b;van Dijk & Visser, 1971) are 2.01 (1) and 2.02 (1) A, with CSSC dihedral angles of 66.4 and 92.1 °, respectively.…”

Section: Introductionmentioning

confidence: 66%

“…The sulfur-sulfur bond lengths reported for dicinnamyl disulfide (lee & Bryant, 1971) and dibenzyl disulfide (Lee & Bryant, 1969b;van Dijk & Visser, 1971) are 2.01 (1) and 2.02 (1) A, with CSSC dihedral angles of 66.4 and 92.1 °, respectively. Hordvik (1966) gives 2.03-2.05 A as the expected length of an aliphatic S-S bond. Although CSSC dihedral angles of 105 to 110 ° have been reported (Foss, Johnsen & Tvedten, 1958;Foss & Johnsen, 1965;Oughton & Harrison, 1959), values between 80 and 100 ° (Hordvik, 1966;Lee & Bryant, 1969) are usually observed.…”

Section: Introductionmentioning

confidence: 99%

“…Hordvik (1966) gives 2.03-2.05 A as the expected length of an aliphatic S-S bond. Although CSSC dihedral angles of 105 to 110 ° have been reported (Foss, Johnsen & Tvedten, 1958;Foss & Johnsen, 1965;Oughton & Harrison, 1959), values between 80 and 100 ° (Hordvik, 1966;Lee & Bryant, 1969) are usually observed. Repulsion between the lone-pair electrons is expected to be at a minimum when the dihedral angle is 90 ° (Bergson, 1957).…”

Section: Introductionmentioning

confidence: 99%

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The crystal and molecular structure of bis[2-(N,N-dimethylamino)ethyl]disulfide dihydrochloride

Ottersen¹,

Warner²,

Seff³

1973

Acta Crystallogr Sect B

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The crystal and molecular structure of bis- [2-(N,N-dimethylamino)ethyl]disulfide dihydrochloride [alternatively named 2,2"-dithiobis-(N,N-dimethyl)ethylamine dihydrochloride] has been determined crystallographically using the 1972 unique and significant reflections for which 20< 52 °, and refined to an R index of 0.043. Counter methods with graphite monochromatized Mo K~ radiation were employed. All hydrogen atoms were located on a difference Fourier function. Crystals form in the monoclinic space group P21/c with cell dimensions a = 11"646 (2), b = 11"065 (2), c = 12.370 (3) ,~ and/~ = 112.40 (2) °.Estimated standard deviations in non-hydrogen bond lengths range from 0.001 to 0.005 A and, in angles, from 0.11 to 0-26 °. The sulfur-sulfur bond length is found to be 2.037 (1) A with a dihedral angle of 82.4 (2) °. A short intermolecular contact (3.55 A) between a sulfur atom and a chloride ion is observed.

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Bond-length/Dihedral-angle and Bond-length/Bond-order Relationships for Sulphur(II)-Sulphur(II) Bonds.

Cited by 115 publications

References 0 publications

The crystal and molecular structure of the enol form of 3,3'-dithiobis-(2,4-pentanedione)

The crystal and molecular structure of the enol form of 3,3'-dithiobis-(2,4-pentanedione)

(4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)sodium tetratelluride(2-)

The crystal and molecular structure of bis[2-(N,N-dimethylamino)ethyl]disulfide dihydrochloride

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