One Pot Synthesis of Novel 4-[(5-Aryl-1,3,4-thiadiazol-2-ylamino)methyl]phenol Derivatives

刘汉文,; 裴文丑,; 唐子龙,

doi:10.6023/cjoc1110131

Cited by 1 publication

(1 citation statement)

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“…As regards the effect of substituents on the reducibility of organic compounds, it has been studied in‐depth by many chemical researchers. Celik and Zhu have studied the reduction of these compounds containing XPhCHNG or GCHNPhY structure, and Sauro has studied the reduction potential ( E Red ) of aryl‐substituted acetophenone azines (XPhC (Me)N–NC (Me)PhY. Celik, Zhu, and Sauro all have observed that the E Red values of CN bonds in the investigated compounds are linearly correlated to the Hammett parameter σ of substituents X and Y. Heyes studied the reductions of the pyrylium and thiopyrylium cations.…”

Section: Introductionmentioning

confidence: 99%

Additional effect of para‐hydroxyl on the reduction potentials of theN‐benzylidenebenzenamines

Cao

Zhou

Cao

2019

J of Physical Organic Chem

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The reduction potential E Red of disubstituted N-benzylidenebenzenamines XArCH NArY (abbreviated as XBAY) is a measure of the electron acceptance ability of the Lowest-energy Unoccupied Molecular Orbital (LUMO) in molecule, which is closely related to the electronic effects of substituents X and Y in molecule. Previous studies on the E Red of XBAY reported by Luo, Wang, and Yuan all did not involve these molecules containing hydroxyl. In this work, 28 samples of disubstituted N-benzylidenebenzenamines containing parahydroxyl, (abbreviated as 4-OHBAY or XBAOH-4 0 ) were synthesized, and their E Red values were measured. Then, 127 compounds were taken as a complicated E Red data set, which involved 28 compounds (4-OHBAY and XBAOH-4 0 ) of this work and 99 compounds XBAY reported by Luo. Based on these data E Red set, through a quantitative regression analysis method and comparison of the factors affecting the E Red , the following results are obtained: (a) Because the phenolic hydroxyl OH can dissociate H + to form phenolic oxygen anion, the change regularity of E Red of compounds 4-OHBAY and XBAOH-4 0 is somewhat different from that of E Red of XBAY compounds without hydroxyl OH. That is, hydroxyl OH has an additional effect on the E Red , which decreases the E Red value. (b) The additional effects of 4-OH on the E Red is different from that of 4 0 -OH. The effect of hydroxyl OH attached to the aldehyde aromatic ring on the E Red is more than that of OH attached to the amine aromatic ring. K E Y W O R D Sadditional effect, para-hydroxyl N-benzylidenebenzenamine, reduction potential, substituent electronic effect

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Section: Introductionmentioning

confidence: 99%