Sulfur-sulfur lone pair and sulfur-naphthalene interactions in naphtho[1,8-b,c]-1,5-dithiocin

Glass, Richard S.; Andruski, Stephen W.; Broeker, Jeffrey L.; Firouzabadi, Habib; Steffen, L. Kraig; Wilson, George S.

doi:10.1021/ja00193a041

Cited by 86 publications

(32 citation statements)

References 8 publications

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“…This can be attributed to the presence of an HgÀ ÀS covalent bond in the latter compounds. These distances are slightly larger than those observed in Naptho [1,8-b,c]71,5dithiocin (avg 2.926 Å ) [30] but smaller than twice the van der Waals radius of S (3.70 Å ) [31]. Table 3.…”

Section: [Hgcl 4 ][(Nhmentioning

confidence: 72%

Solution behavior of Hg(II)-cystamine by Uv-Vis and¹⁹⁹Hg NMR

Bharara

Parkin

Atwood

2005

Main Group Chemistry

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Section: [Hgcl 4 ][(Nhmentioning

confidence: 72%

Solution behavior of Hg(II)-cystamine by Uv-Vis and¹⁹⁹Hg NMR

Bharara

Parkin

Atwood

2005

Main Group Chemistry

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“… Compound 28 , with face‐to‐face disulfide contacts, shows a SS separation of 3.182(1) Å 27. The two molecules of compound 30 , in which the sulfide groups are not too far from both being in the aromatic plane and thus edge on to each other, show SS separations of 2.918(2) and 2.934(2) Å,28 and other intramolecular contacts between the shorter radii for sulfide and thiocarbonyl sulfur atoms have been observed at about 2.9 Å 20 . peri ‐Naphthalene 29 with an edge‐to‐face contact between the sulfide groups has an intermediate S⋅⋅⋅S separation (3.005(1) Å) 27.…”

Section: Discussionmentioning

confidence: 99%

Weak Attractive Interactions between Methylthio Groups and Electron‐Deficient Alkenes in peri‐Naphthalenes: A Competition with Conjugative Effects

O'Leary

Wallis

2006

Chemistry A European J

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The solid-state conformations of five peri-disubstituted naphthalenes bearing a methylthio group and an electron-deficient alkene indicate a weak attractive interaction between the functional groups in four cases in which out-of-plane displacements lead to a common orientation of the MeSsp(2)-C vector to the alkene bond. In some cases the interaction is not strong enough to outweigh the tendency of the alkene to conjugate with the aromatic ring, and in one case this optimisation of conjugation alone controls the molecular conformation. The methylthio group lies close to the aromatic plane in all but one example for which the plane of the sulfide group is presented to the alkene.

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“…Cyclic dichalcogenides 3 are the example of cis ‐dichalcogenides. Another aim of the analysis is to construct the firm basis to clarify the E—E' trans ‐annular interactions in cyclo ‐E(CH 2 CH 2 CH 2 ) 2 E' ( 4 ), their dications ( 4 2+ ) and the dimers ( 4 2 2+ ) reported by research groups of Furukawa and Glass . The cyclic dichalcogenides 3 are the candidates for the purpose.…”

Section: Introductionmentioning

confidence: 99%

Dynamic and Static Behavior of E–E' Bonds in Neutral and Charged Forms of HEE'H, MeEE'Me, andCyclo‐1,2‐EE'(CH₂)₃(E, E' = O, S, Se, and Te) Elucidated by AIM Dual Functional Analysis

Hayashi

Matsuiwa

Miza

et al. 2014

Heteroatom Chemistry

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The nature of the E‐*‐E' bonds in neutral, monoanionic, monocationic, and dicationic forms of HEE'H (1), MeEE'Me (2), and cyclo‐1,2‐EE'(CH2)3 (3) (E, E' = O, S, Se, Te) is investigated by applying AIM (atoms‐in‐molecules method) dual functional analysis. Hb(rc) are plotted versus Hb(rc) – Vb(rc)/2 for the data of E‐*‐E' at bond critical points (BCPs) of fully optimized structures and perturbed structures around the fully optimized ones. Plots for the fully optimized structures are analyzed by the polar coordinate (R, θ) representation. The (θp, κp) parameters are derived from those of the perturbed structures: θp corresponds to the tangent line of each plot, and κp is the curvature. While (R, θ) correspond to the static nature, (θp, κp) represent the dynamic nature of interactions. The nature of E‐*‐E' in the neutral and charged species is classified by comparing their θ and θp values with those of the standard interactions as a reference. Data for E‐*‐E' in the neutral forms of 1–3 appear in the shared‐shell (SS) region (180° < θ), except for MeS‐*‐TeMe (2c), which does in the regular closed‐shell (CS) region (90° < θ < 180°). The E–E' bonds in the monoanionic forms of 1–3 become much longer and weakened. Therefore, data of the monoanionic forms appear in the regular CS. On the other hand, the strengths of E‐*‐E' in the mono‐ and dicationic forms are almost equal to those in the neutral forms of 1–3 in the plots, irrespective of the shorter E‐*‐E' lengths in the cationic forms, relative to the neutral forms.

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Sulfur-sulfur lone pair and sulfur-naphthalene interactions in naphtho[1,8-b,c]-1,5-dithiocin

Cited by 86 publications

References 8 publications

Solution behavior of Hg(II)-cystamine by Uv-Vis and¹⁹⁹Hg NMR

Solution behavior of Hg(II)-cystamine by Uv-Vis and¹⁹⁹Hg NMR

Weak Attractive Interactions between Methylthio Groups and Electron‐Deficient Alkenes in peri‐Naphthalenes: A Competition with Conjugative Effects

Dynamic and Static Behavior of E–E' Bonds in Neutral and Charged Forms of HEE'H, MeEE'Me, andCyclo‐1,2‐EE'(CH₂)₃(E, E' = O, S, Se, and Te) Elucidated by AIM Dual Functional Analysis

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Sulfur-sulfur lone pair and sulfur-naphthalene interactions in naphtho[1,8-b,c]-1,5-dithiocin

Cited by 86 publications

References 8 publications

Solution behavior of Hg(II)-cystamine by Uv-Vis and199Hg NMR

Solution behavior of Hg(II)-cystamine by Uv-Vis and199Hg NMR

Weak Attractive Interactions between Methylthio Groups and Electron‐Deficient Alkenes in peri‐Naphthalenes: A Competition with Conjugative Effects

Dynamic and Static Behavior of E–E' Bonds in Neutral and Charged Forms of HEE'H, MeEE'Me, andCyclo‐1,2‐EE'(CH2)3(E, E' = O, S, Se, and Te) Elucidated by AIM Dual Functional Analysis

Contact Info

Product

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Solution behavior of Hg(II)-cystamine by Uv-Vis and¹⁹⁹Hg NMR

Solution behavior of Hg(II)-cystamine by Uv-Vis and¹⁹⁹Hg NMR

Dynamic and Static Behavior of E–E' Bonds in Neutral and Charged Forms of HEE'H, MeEE'Me, andCyclo‐1,2‐EE'(CH₂)₃(E, E' = O, S, Se, and Te) Elucidated by AIM Dual Functional Analysis