Comparison of two independent structure determinations of diphenyl disulphide

Sacerdoti, M.; Gilli, G.; Domiano, P.

doi:10.1107/s0567740875002683

Cited by 43 publications

(31 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…6) According to the literature there are several MO calculations in which a preference of the gauche (cis) form over the anti (trans) form in relation to the disulfide linkage and an energy minimum in the dihedral angle near 90°have been shown. 7,8) Furthermore, some structural data for comparatively simple disulfides such as dimethyl disulfide, 9,10) dibenzyl disulfide, 11) and diphenyl disulfide 12,13) by other investigators were in agreement with this prediction. However, there have not been many studies on the conformations of disulfide compounds and a more detailed investigation of their conformations is still valuable.…”

supporting

confidence: 70%

“…3-85.8°a nd these values are slightly lower than those (83.9-96.6°) in the MO calculations and structural data described above. [7][8][9][10][11][12][13] Syntheses of 1-(Benzoylthio)indolizine Derivatives According to the procedure described earlier by us 14) these 1-benzoylthio-2-(R-thio)indolizine derivatives 4a-x were synthesized from the S-alkylation of pyridinium 1-[2-(R-thio)-2-thioxo]ethanides (1a-x) with phenacyl bromide (2), followed by the treatment of the resulting pyridinium salts (3a-x) with 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) and chloranil in chloroform at 0°C. These results are summarized in Chart 1.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Preparation of New Nitrogen-Bridged Heterocycles. 60. Syntheses and Conformational Analyses of Bis(indolizin-1-yl) Disulfides

Kakehi

Suga

Okuno

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

In our preceding papers we described that the conformational stability of a sulfide linkage is inherently in the following order: gauche formϾanti formϾeclipse form, irrespective of the presence of some attractive interaction between the substituents on the terminal atoms, but the difference in the formation energies of the optimized gauche and anti conformation is not large.1,2) This order was also consistent with our experimental results observed for various 3-(R-thio)-thieno [3,4-b]indolizine derivatives, [1][2][3][4][5] and the extra presence of the intramolecular p-p interaction made one of the gauche conformations more predominant than the other gauche and anti ones in the solution state. These molecules can be novel candidates for investigating face selectivity or conformational control through a single bond. As an extension of this work, we are interested in the conformation about the disulfide linkage, since we previously found a similar phenomenon in the X-ray analysis of bis [thieno[3,4-b]indolizin-3-yl] disulfide. 6) According to the literature there are several MO calculations in which a preference of the gauche (cis) form over the anti (trans) form in relation to the disulfide linkage and an energy minimum in the dihedral angle near 90°have been shown. 7,8) Furthermore, some structural data for comparatively simple disulfides such as dimethyl disulfide, 9,10) dibenzyl disulfide, 11) and diphenyl disulfide 12,13) by other investigators were in agreement with this prediction. However, there have not been many studies on the conformations of disulfide compounds and a more detailed investigation of their conformations is still valuable. We selected bis(indolizin-1-yl) disulfide derivatives as the model compound for the following reasons: 1) an effective method for the preparation of these compounds has been already developed by us 14); 2) their Mopac PM3 calculations 15) supported the appearance of exclusive or nearly exclusive gauche forms; and 3) the participation of the intramolecular p-p interaction between the two indolizin-1-yl groups can be expected. In this paper we report the facile syntheses and the conformations of some bis(indolizin-1-yl) disulfide derivatives. Results and DiscussionConformational Analyses of Some Bis(indolizin-1-yl) Disulfides by Molecular Calculations Considering the molecular structures of bis[2-(R-thio)indolizin-1-yl] disulfides (5) (see Chart 2), the 6 most probable conformations were selected for calculation ( Fig. 1): two anti forms A1 and A2, and 4 gauche forms G1 with an intramolecular p-p interaction, G2, G3, and G4. Since the gauche forms G3 and G4 are enantiomeric, however, the Mopac PM3 calculations 15) were performed for the A1, A2, G1, G2, and G3 of Compounds 5a-e, i. The relative formation energy and one torsion angle (C-S-S-C) in the respective optimized conformations using the G3 form as a standard are listed in Table 1. As expected, all or the majority of the A1 or A2 forms were changed to the G1 and G2 or G3 and G4 forms respectively during the optimized...

show abstract

supporting

confidence: 70%

mentioning

confidence: 99%

Preparation of New Nitrogen-Bridged Heterocycles. 60. Syntheses and Conformational Analyses of Bis(indolizin-1-yl) Disulfides

Kakehi

Suga

Okuno

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…The C(1)-S(2) and C(3)-S(3) distances are slightly shorter than S-C(sp 2) single bonds, e.g. 1.747 A in $3(SO2Ph)2 (Chen & Wang, 1984) and 1-789, 1.788A in (PhS)2 (Sacerdoti & Gilli, 1975). Unlike those of (1), the two endocyclic S-C bond lengths are identical within their standard deviations.…”

mentioning

confidence: 86%

Structure of 5-(p-methoxyphenyl)-3H-1,2-dithiole-3-thione, C10H8OS3

Wang¹,

Lin²,

Wei³

1985

Acta Crystallogr C

View full text Add to dashboard Cite

“…An extraordinarily long C-C bond of 1.64 A was predicted for hexaphenylethane (Hounshell, Dougherty, Hummel & Mislow, 1977). Comparable C-S bond lengths and C-S-C bond angles are: 1.847(2) A, 76.8(3) ° in trimethylene sulfide (Karakido & Kuchitsu, 1975) (Sacerdoti, Gilli & Domiano, 1975), 1.785 (2) A in di-2-pyridyl disulfide (Raghavan & Serf, 1977), 1.776(6) A, 103 ° in di-o-tosyl sulfide (Sarcerdoti, Bertolasi & Gilli, 1976).…”

Section: -C(mi)-c(1a)-c(2a)mentioning

confidence: 99%