TY - JOUR
T1 - Comments on some chemical properties of diphenyl disulfide and its derivatives
T2 - II.Correlating the studies of reductive cleavage of disulfide bonds with the studies of anti-human immunodeficiency virus activity with lowest unoccupied molecular orbital properties
AU - Lin, Hung Sung
AU - Wu, Yan
AU - Liu, Yu Ju
AU - Chen, Shu Hui
AU - Chen, Wei Ting
AU - Wang, Shao Pin
N1 - Publisher Copyright:
© 2020 Chemical Society Located in Taipei and Wiley-VCH Verlag GmbH & Co. KGaA
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/11
Y1 - 2020/11
N2 - The higher anti-human immunodeficiency virus activity of a symmetrical 2,2′-disubstitued derivative of diphenyl disulfide (DPDS) has been explained by the lower energy of the lowest unoccupied molecular orbital (LUMO), resulted from a better hydrogen bond stabilization of the σ*SS bond orbital (BO). This conclusion entails the participation of σ*SS BO in constructing the LUMO. The higher content of σ*SS BO, compared to π*CC BOs of phenyl groups, in LUMO of DPDS has been found through analysis of the LUMO of DPDS expanded in the BO space. The high content of σ*SS BO (%σ*SS) in the LUMO of DPDS has laid the foundation for the formation of σ-type radical anion intermediate in the stepwise reductive cleavage of disulfide bond in the symmetrical 4,4′-disubstitued DPDS derivatives. For the nine 4,4′-disubstituted DPDS-derivatives under reductive cleavage studies, the increasing %σ*SS in the LUMOs is parallel to the increasing value of inner reorganization energy.
AB - The higher anti-human immunodeficiency virus activity of a symmetrical 2,2′-disubstitued derivative of diphenyl disulfide (DPDS) has been explained by the lower energy of the lowest unoccupied molecular orbital (LUMO), resulted from a better hydrogen bond stabilization of the σ*SS bond orbital (BO). This conclusion entails the participation of σ*SS BO in constructing the LUMO. The higher content of σ*SS BO, compared to π*CC BOs of phenyl groups, in LUMO of DPDS has been found through analysis of the LUMO of DPDS expanded in the BO space. The high content of σ*SS BO (%σ*SS) in the LUMO of DPDS has laid the foundation for the formation of σ-type radical anion intermediate in the stepwise reductive cleavage of disulfide bond in the symmetrical 4,4′-disubstitued DPDS derivatives. For the nine 4,4′-disubstituted DPDS-derivatives under reductive cleavage studies, the increasing %σ*SS in the LUMOs is parallel to the increasing value of inner reorganization energy.
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U2 - 10.1002/jccs.202000044
DO - 10.1002/jccs.202000044
M3 - Article
AN - SCOPUS:85091691318
VL - 67
SP - 2149
EP - 2152
JO - Journal of the Chinese Chemical Society
JF - Journal of the Chinese Chemical Society
SN - 0009-4536
IS - 11
ER -