Chalcone유도체에 대한 Thioglycolic acid의 친핵성 첨가 반응메카니즘과 그 반응 속도론적 연구

박은경 명지대학교 대학원 1990 국내석사

The kinetics of the addition of chalcone derivatives was investigated by ultraviolet spectrophotometery in 5% dioxane-H(2)O at 50℃. A rate equation was obtained in wide range of pH. The substituent effects on chalcone derivatives were studied, and addition were facilitated by electron attracting groups. The final product was chalcone-β-thioglycolic acid synthesized by the addition of thioglycolic acid to chalcone. On the base of the rate equation, substitutent effect, general base effect and final product, the plausible addition mechanism was proposed: Below pH 9.0, only neutral thioglycolic acid molecule was added to the carbon-carbon double bond, and in the range of pH9.0-11.0, neutral thioglycolic acid molcule and thioglycolic acid anion competitively attacted the double bond. By contrast, above pH11.0, the reaction was dependent upon only the addition of thioglycolic acid anion. Chalcone유도체에 대한 thioglycolic acid 의 첨가 반응 속도를 50℃의 5% dioxane 수용액 중에서 자외선 분광기를 사용하여 측정하였다. Chalcone 유도체에 thioglycolic acid를 첨가시켰을 때 친핵성 첨가 반응 속도에 미치는 치환기 효과를 검토하기 위하여 Hammett plot를 한 결과 전자 유인성 기에 의하여 반응 속도가 촉진됨을 확인할 수 있었다. 한편, chalcone에 thioglycolic acid를 반응시켰을 때의 생성물은 chalcone-β-thioglycolic acid이었으며 반응 속도 상수의 변화, 치환기 효과 및 general base 효과등의 결과로부터 Chalcone에 대한 thioglycolic acid의 친핵성 첨가 반응은 pH 1.0 ~ 9.0 에서는 thioglycolic acid의 중성분자가, pH 9.0 ~ 11.0에서는 thioglycolic acid의 중성 분자와 그의 음이온이 경쟁적으로 첨가되며, PH 11 이상에서는 음이온만이 첨가됨을 알 수 있었다.

Thioglycolic acid를 이용한 황-포함 작용기 도입에 관한 연구

신영진 성신여자대학교 일반대학원 2021 국내석사

C-S bond formation is important for the synthesis of various chemicals such as pharmaceuticals, pesticides, and polymer materials. Several reagents such as H2S, NaSH, sulfur powder, etc. have been used as sulfur source for the C-S coupling. However, they have some limitations; they are highly reactive and toxic, and have unpleasant odor. Thioglycolic acid can be a complementary sulfur source for copper-catalyzed C-S bond forming reactions and the most important variable in this reaction is the solvent; polar aprotic solvents such as DMSO or DMF work best. Interestingly, several different C-S bond containing products were obtained depending on the reaction solvents. Each optimized protocol gave biaryl disulfide and 2-(phenylthio)acetic acid, respectively. Thioglycolic acid can be also used to introduce a thioformyl group into amines. Thioformyl group are often used as an intermediate of various compounds. However, its synthetic methods have been rarely reported. Toxic H2S gas or reagents of low atom economy are required to prepare thioformamides. Yet, these reagents produce a very limited variety of thioformamide. This study discovered that the introduction of thioformyl group into primary and secondary amines and aniline is possible by using of thioglycolic acid in the absence of a transition metal catalyst.

퍼머넌트제의 웨이브 효율과 모발손상 비교

이종숙 建陽大學校 保健福祉大學院 2007 국내석사

The hair style of women was enlarged its importance of an aesthetic point of view as a means of self-expression. In proportion to the desire of strong personality expression, chemical treatments on hair as well as repeat and crossing treatments were increased. Particularly permanent wave treatment was the most popular style in woman. But the excessive chemical treatments cause not only hair damage but also impede personality expressions and brings about serious obstacles at an aesthetic point of view. Thus various permanent wave lotions were investigated and sales on the market. The permanent wave lotions have two face, the one is the efficacy of waves and the another is damage of hair. These two points were dependent factor to each other. For the purpose of the investigation on correlation of these two factors, the wave efficacy and hair damage following chemical treatments, using 4 different permanent wave lotions, these were thioglycolic acid, cysteine, cysteine HCl and cysteamine. In order to this experiment, three women's healthy hairs are picked and executed permanent, colorings, and decoloration treatments. To find out the efficiency of permanent wave lotion, the efficiency of permanent wave and the maintenance ratio of the wave were measured. By comparing the before and after of perm processing, the efficiency of wave was evaluated and the maintenance ratio of wave was observed and calculated by observing the changes of curl after alkali-processing of the wave-formed hair. The wave efficiency was potent orderly cysteamine, cysteine, cysteine HCl and thioglycolic acid. Repeated operation, these results were similar to simple operation and resulted more potent differences. The pH of permanent wave lotion were highest at 9.18 in case of thioglycolic acid and other formulations were below 9. The elasticity of hair, maximum length returning to an orignal situation when pulling hair and unloose it were evaluated. We measured the moisture retention of hair, the degree of moisture retention at the dry condition after supplying sufficient moisture with hair and alkali solubility, the quantity of hair protein dissolving and coming out at alkali and also analysed and evaluated cystine content existing in the hair. Through these results on hair damage ratios were orderly thioglycolic acid, cysteine, cysteine HCl and cysteamine. Also the same patterns were shown in physical touch test following permanent operation but the difference was not important among permanent wave lotions. The elasticities were 134.8 % in case of virgin hair but in case of thioglycolic acid was diminished as 121.2 %. In case of cysteamine it was 129.8 % as relatively high value could verify a low hair damage. In chemical damage tests, operation of permanent wave aggressive damage on hair but the choice of permanent wave lotion could reduce it. Moisturizing effects of virgin hair was 14.0 %, 12.0 % of thioglycolic acid and 12.8 % of cysteamine. In alkali release tests, damaged hair had high level of protein loose value such as thioglycolic acid compared with cysteine and cysteamine. Similar results were shown in cystine release patterns. These results were shown the correlation with hair damage and wave effectivity of permanent wave lotion.

α-Cyano-β-phenylacrylic acid에 대한 Thioglycolic acid첨가 생성물의 합성

유희종 성심여자대학교 대학원 1983 국내석사

α-시아노 아세트산 칼륨과 벤즈알데히드 유도체로 부터, α-시아노-β-페닐아크릴산 유도체를 합성하고, α-시아노-β-페닐아크릴산 유도체에 티오글리콜산을 첨가시켜, 지금까지 보고된 바 없는 다음과 같은 다섯가지 새로운 화합물을 합성하였으며, uv, ir 및 nmr 스펙트럼 등으로 이 화합물의 구조를 확인하였읍니다. (3-Cyano-2-phenyl-4-oxo-tetrahydro)-thiophene. [3-Cyano-2-(p-methyl phenyl)-4-oxo-tetrahydro]-thiophene. [3-Cyano-2-(p-methoxyphenyl)-4-oxo-tetrahydro]-thiophene. [3-Cyano-2-(p-chloro phenyl)-4-oxo-tetrahydro]-thiophene. [3-Cyano-2-(3,4,5-tri-methoxy phenyl)-4-oxo-tetrahydro]-thiophene. Five new compounds were synthesized by the cyclization reaction of thioglycolic acid to the derivatives of α-Cyano-β-phenyl acrylic acid. (3-Cyano-2-phenyl-4-oxo-tetrahydro)-thiophene. [3-Cyano-2-(p-methyl phenyl)-4-oxo-tetrahydro]-thiophene. [3-Cyano-2-(p-methoxyphenyl)-4-oxo-tetrahydro]-thiophene. [3-Cyano-2-(p-chlorophenyl)-4-oxo-tetrahydro]-thiophene. [3-Cyano-2-(3,4,5-tri-methoxyphenyl)-4-oxo-tetrahydro]-thiophene. The structures of these compounds were identified by means of ultraviolet, infrared and n.m.r. spectra.

β-Nitrostyrene 유도체에 대한 Thioglycolic acid의 친핵성 첨가반응에 관한 반응속도론적 연구

한인섭 高麗大學校 1980 국내박사

Vinyl sulfilimine에 대한 Thioglycolic acid의 친핵성 첨가물의 합성과 그의 반응메카니즘에 대한 연구

한만소 高麗大學校 1989 국내석사

1-Chloro-1-phenyl-2-carboethoxy-2-cyanoethene 誘導體에 對한 Thioglycolic acid 添加物의 合成

이만구 圓光大學校 1982 국내석사

β,β-Dichlorostyrene의 合成과 Thioglycolic Acid 및 Cysteine의親核性添加反應에 關한 反應逮度論的 硏究

유정열 고려대학교 1980 국내석사