Microwave Spectra, Molecular Structure, and Electric Dipole Moment of 1,2-Dithiin

Gillies, J. Z.; Gillies, C. W.; Cotter, E. A.; Block, Eric; DeOrazio, Russell J.

doi:10.1006/jmsp.1996.0232

Cited by 26 publications

(24 citation statements)

References 10 publications

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“…There is a reversible oxidation at 0.67 -0.745 V in CH 3 CN and 0.81-0.85 V in CH 2 C1 2 followed by an irreversible oxidation at higher potential (1.03-1.40 V) except for lb which shows only irreversible oxidations at 0.96 and 1.26 V in CH 3 poses the oxidation potential of 2 was measured under these conditions and found to be 1.13 and 1.04 V in CH 2 C1 2 and CH 3 CN, respectively.…”

Section: Electrochemistrymentioning

confidence: 94%

Spectroscopic, Theoretical, and Electrochemical Studies of 1,2-Dithiins

Glass

Pollard

Schroeder

et al. 1997

Phosphorus, Sulfur, and Silicon and the Related Elements

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The lowest oxidation potentials for 1,2-dithiins are in the range of 0.67-0.96 V in acetonitrile and 0.81-1.04 V in dichloromethane. These oxidation potentials are less anodic than expected based on the ionization potentials of 1,2-dithiin determined by photoelectron spectroscopy. Theoretical calculations suggest that the reason for this difference is a change in optimized geometry between 1,2-dithiin and its oxidized species.

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Section: Electrochemistrymentioning

confidence: 94%

Spectroscopic, Theoretical, and Electrochemical Studies of 1,2-Dithiins

Glass

Pollard

Schroeder

et al. 1997

Phosphorus, Sulfur, and Silicon and the Related Elements

View full text Add to dashboard Cite

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“…(6), (8) and (11) we can see that the sum of the roots of the secular equations does not contain the constants of vibronic coupling between the terms. Indeed, for interaction of only two terms this is seen directly from the sum of the two solutions (6), while for the cubic equation (8) and fourth order equation (11) it follows from the well-known algebra relation. For the three roots e 1 ; e 2 ; and e 3 of Eq.…”

Section: Excited States Energy Profiles and Vibronic Coupling Constmentioning

confidence: 96%

“…In so doing we can avoid calculating the roots of Eqs. (8) and (11), using instead their combinations in Eqs. (12) and (13) and fitting them to the corresponding values of these combination of the energies obtained from the ab initio calculated energy profiles of the corresponding terms.…”

Section: Moleculesmentioning

confidence: 99%

“…(9) and (11) in terms of all these constants are cumbersome, while direct calculation of the constants is difficult. However, the latter can be estimated by means of ab initio calculations of corresponding energy profiles and employing a procedure of fitting the equations above to the results of ab initio calculations (Section 4).…”

Section: Geometry Parameters Moleculesmentioning

confidence: 99%

“…Structural studies of 1,2-dithiin reveal that its high-symmetry planar C 2v configuration is unstable, and it has a twisted equilibrium structure with C 2 symmetry in equilibrium [11]. Ab initio calculation of 3,6-flouroalkyl 1,2-dithiin derivatives show that these compounds adopt a twisted geometry for both 1,2-dithiin and related 1,2-diselenin [1].…”

Section: Introductionmentioning

confidence: 98%

See 2 more Smart Citations

Pseudo Jahn-Teller origin of instability of planar configurations of hexa-heterocycles. Application to compounds with 1,2- and 1,4-C4X2 skeletons (X = O, S, Se, Te)

2015

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3,6-Bis(p-dimethylaminophenyl)-1,2-dithiin versus 3,4-Bis(p-dimethylaminophenyl)-1,2-dithiete – A Mechanistic Probe for the Photoinduced Behavior of the 1,2-Dithiin System©

Schroth¹,

Spitzner

Bruhn

1998

Eur. J. Org. Chem.

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Whereas 3,4‐bis(p‐dimethylaminophenyl)‐1,2‐dithiete (18) is in equilibrium with its ring‐opened valence isomer 19/19′, which can also exist as a solid, the analogously disubstituted 1,2‐dithiin 20 is stable when protected from light, but on exposure to light undergoes immediate ring transformation to 2,5‐bis(p‐dimethylaminophenyl)thiophene‐3‐thiol (30). To a lesser extent, it also undergoes sulfur extrusion to form 2,5‐bis(p‐dimethylaminophenyl)thiophene (29). The ring‐opened valence isomer 21/21′ and dihydrothiophene episulfide 28 are suggested as key intermediates. X‐ray crystallography of the disulfide 31 obtained from the main product 30 unequivocally confirms the structure. The synthesis of 20 is based on the nucleophilic addition of 1,1‐dimethylethanethiol to 1,4‐bis(p‐dimethylaminophenyl)butadiyne (23a) with ensuing functional group conversion. An efficient variant of this method using ethoxycarbonylsulfenyl chloride as a deprotecting reagent is described, leading to the synthesis of 3,6‐diphenyl‐1,2‐dithiin (27).

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Microwave Spectra, Molecular Structure, and Electric Dipole Moment of 1,2-Dithiin

Cited by 26 publications

References 10 publications

Spectroscopic, Theoretical, and Electrochemical Studies of 1,2-Dithiins

Spectroscopic, Theoretical, and Electrochemical Studies of 1,2-Dithiins

Pseudo Jahn-Teller origin of instability of planar configurations of hexa-heterocycles. Application to compounds with 1,2- and 1,4-C4X2 skeletons (X = O, S, Se, Te)

3,6-Bis(p-dimethylaminophenyl)-1,2-dithiin versus 3,4-Bis(p-dimethylaminophenyl)-1,2-dithiete – A Mechanistic Probe for the Photoinduced Behavior of the 1,2-Dithiin System©

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