The Dipole Moments of Diphenyl Sulfide, Sulfoxide, Sulfone, and Their Derivatives

Toshiyasu, Yoshio; Taniguchi, Yoshio; Kimura, Ko; Fujishiro, Ryoichi; Yoshihara, Masakuni; Tagaki, Waichiro; Ōae, Shigeru

doi:10.1246/bcsj.42.1878

Cited by 13 publications

(5 citation statements)

References 7 publications

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“…In addition to the large partial charges, the diphenylsulfone part of the R-BAPS monomer unit is characterized by a substantial dipole moment. The value of this dipole moment can be used for verification of the atomic charges: It turns out that the calculated dipole moment of the diphenylsulfone part of the R-BAPS monomer unit (μ = 6.1 D) agrees rather well with experimental values of the dipole moment of diphenylsulfone molecules (μ ∼ 5.1 D). − …”

Section: Model and Simulation Methodologymentioning

confidence: 60%

Microsecond Atomic-Scale Molecular Dynamics Simulations of Polyimides

et al. 2013

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We employ microsecond atomic-scale molecular dynamics simulations to get insight into the structural and thermal properties of heat-resistant bulk polyimides. As electrostatic interactions are essential for the polyimides considered, we propose a two-step equilibration protocol that includes long (microsecond-scale) MD simulations of polymer melt with partial atomic charges switched off, followed by relatively short runs (100 ns) of the polymer system with full electrostatics. We demonstrate that macroscopic characteristics of a polyimide sample (such as the glass transition temperature and density) are not particularly sensitive to the degree of equilibration. However, great caution should be paid when local structural characteristics are considered: proper equilibration of the local polymer structure (monitored through the radius of gyration and the end-to-end distance of individual chains) is found to require simulations on a microsecond time scale. Finally, we found a dramatic impact of electrostatic interactions on the properties of the bulk polyimides considered: when intra-and intermolecular dipole−dipole interactions come into play we witness compaction of individual polymer coils and eventually an increase in the glass transition temperature and polymer density.

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Section: Model and Simulation Methodologymentioning

confidence: 60%

Microsecond Atomic-Scale Molecular Dynamics Simulations of Polyimides

et al. 2013

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“…Phillips et al 28 proposed double bond characteristics of the S-O bond based on small dipole moments (2.2-2.9 D) of the S-O linkage, a short bond length and greater bond strength. However Cumper and Walker 29 recalculated the dipole moments and found that the dipole moment is in the range of 2.8 to 4.3 D. Similarly Toshiyasu et al 30 determined the dipole moment of the diaryl sulfone as high as 4.5 D. These larger dipole moments suggest that the S-O linkage as charge separated. This indicates that the sulfones and sulfonamides act as strong electron withdrawing groups and could decrease the electron density significantly in the vinyl group resulting in a harder terminal β-carbon electrophile.…”

Section: Resultsmentioning

confidence: 99%

Intrinsic reactivity profile of electrophilic moieties to guide covalent drug design: N-α-acetyl-l-lysine as an amine nucleophile

et al. 2016

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“…As shown in Fig. 1, PPS has a structure in which two phenyl rings are bonded by S with a bond angle ∠C–S–C of 110 [5], which gives a comparatively large dipole moment of 1.46 D [6] to the structure of diphenyl sulfide. However, since the molecular chain has a zigzag structure as shown in Fig.…”

Section: Discussionmentioning

confidence: 99%

Dielectric properties of poly(phenylene sulfide) as a function of temperature and frequency

Hikosaka

Ohki²

2011

IEEJ Transactions Elec Engng

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Dielectric properties of poly(phenylene sulfide) (PPS), a kind of super engineering plastic, were investigated over a wide temperature range by measuring its frequency spectra of complex permittivity and thermally stimulated polarization and depolarization currents (TSPC and TSDC). Experimental results indicate that its permittivity and dielectric loss factor remain stable and maintain low values up to around 140 °C, despite the fact that its glass transition appears at a much lower temperature of 88 °C. As for TSPC and TSDC, a very small peak associated with the glass transition appears at about 110 °C. Furthermore, a much clearer TSPC peak due to orientation of dipole moments associated with the ether linkage induced by the cross‐linking reaction appears at about 150–170 °C. The corresponding TSDC peak due to randomization of these dipoles is very small compared to the TSPC peak, since PPS was cross‐linked during the high‐temperature process in the TSPC measurement, which made rotation of the dipoles difficult. At temperatures higher than 150 °C, both the real and imaginary parts of the complex permittivity show significant increases with increase in temperature and decrease in frequency. This is attributable to the transport of the charge carriers. © 2011 Institute of Electrical Engineers of Japan. Published by John Wiley & Sons, Inc.

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The Dipole Moments of Diphenyl Sulfide, Sulfoxide, Sulfone, and Their Derivatives

Cited by 13 publications

References 7 publications

Microsecond Atomic-Scale Molecular Dynamics Simulations of Polyimides

Microsecond Atomic-Scale Molecular Dynamics Simulations of Polyimides

Intrinsic reactivity profile of electrophilic moieties to guide covalent drug design: N-α-acetyl-l-lysine as an amine nucleophile

Dielectric properties of poly(phenylene sulfide) as a function of temperature and frequency

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