Comments on chemical properties reported for diphenyl disulfide and its derivatives: The merit of the phenyl groups

Hung Sung Lin, Yan Wu, Yu Ju Liu, Shu Hui Chen, Wei Ting Chen, Shao Pin Wang

研究成果: Article

摘要

The symmetrical 2,2′-disubstitued derivatives of diphenyl disulfide showing widely spanning rates of electrophilic attack of the HIV-1 nucleocapsid protein p7 zinc fingers have been rationalized, based on the lowest unoccupied molecular orbital (LUMO)-lowering approach, by the substituents' π-effects and the hydrogen bond stabilization effects. In the 2,2′-amide- and 4,4′-N-amide-substituted derivatives, the extent of LUMO lowering has been reduced by the destabilization of lone-pair bond orbital, lp(N), present on the nitrogen atom of N-amide. From the natural bond orbital viewpoint, hydrogen bond stabilization of LUMO is mainly governed by stabilization of the σ*SS bond orbital.

原文English
期刊Journal of the Chinese Chemical Society
DOIs
出版狀態Accepted/In press - 2019 一月 1

指紋

Molecular orbitals
Amides
Chemical properties
Stabilization
Derivatives
Hydrogen bonds
Chemical bonds
Zinc
Nitrogen
Atoms
diphenyl disulfide

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

引用此文

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title = "Comments on chemical properties reported for diphenyl disulfide and its derivatives: The merit of the phenyl groups",
abstract = "The symmetrical 2,2′-disubstitued derivatives of diphenyl disulfide showing widely spanning rates of electrophilic attack of the HIV-1 nucleocapsid protein p7 zinc fingers have been rationalized, based on the lowest unoccupied molecular orbital (LUMO)-lowering approach, by the substituents' π-effects and the hydrogen bond stabilization effects. In the 2,2′-amide- and 4,4′-N-amide-substituted derivatives, the extent of LUMO lowering has been reduced by the destabilization of lone-pair bond orbital, lp(N), present on the nitrogen atom of N-amide. From the natural bond orbital viewpoint, hydrogen bond stabilization of LUMO is mainly governed by stabilization of the σ*SS bond orbital.",
author = "Lin, {Hung Sung} and Yan Wu and Liu, {Yu Ju} and Chen, {Shu Hui} and Chen, {Wei Ting} and Wang, {Shao Pin}",
year = "2019",
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T1 - Comments on chemical properties reported for diphenyl disulfide and its derivatives

T2 - The merit of the phenyl groups

AU - Lin, Hung Sung

AU - Wu, Yan

AU - Liu, Yu Ju

AU - Chen, Shu Hui

AU - Chen, Wei Ting

AU - Wang, Shao Pin

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The symmetrical 2,2′-disubstitued derivatives of diphenyl disulfide showing widely spanning rates of electrophilic attack of the HIV-1 nucleocapsid protein p7 zinc fingers have been rationalized, based on the lowest unoccupied molecular orbital (LUMO)-lowering approach, by the substituents' π-effects and the hydrogen bond stabilization effects. In the 2,2′-amide- and 4,4′-N-amide-substituted derivatives, the extent of LUMO lowering has been reduced by the destabilization of lone-pair bond orbital, lp(N), present on the nitrogen atom of N-amide. From the natural bond orbital viewpoint, hydrogen bond stabilization of LUMO is mainly governed by stabilization of the σ*SS bond orbital.

AB - The symmetrical 2,2′-disubstitued derivatives of diphenyl disulfide showing widely spanning rates of electrophilic attack of the HIV-1 nucleocapsid protein p7 zinc fingers have been rationalized, based on the lowest unoccupied molecular orbital (LUMO)-lowering approach, by the substituents' π-effects and the hydrogen bond stabilization effects. In the 2,2′-amide- and 4,4′-N-amide-substituted derivatives, the extent of LUMO lowering has been reduced by the destabilization of lone-pair bond orbital, lp(N), present on the nitrogen atom of N-amide. From the natural bond orbital viewpoint, hydrogen bond stabilization of LUMO is mainly governed by stabilization of the σ*SS bond orbital.

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