四川大学：《绿色化学》课程教学资源（PPT课件）第四章 设计更加安全化学品的应用 Application of Designing Safer Chemicals

四川大学化学学院 2002年7月26日 1 Chapter 4 Application of Designing Safer Chemicals

四川大学化学学院 2002年7月26日 1 Chapter 4 Application of Designing Safer Chemicals

⚫ 4.1 Isosteric Replacement of Carbon with Silicon (用硅对碳进行等电排置换)in the Design of Safer Chemicals ⚫ 4.2 Designing Biodegradable Chemicals ⚫ 4.3 Designing Aquatically Safer Chemicals ⚫ References

⚫ 4.1 Isosteric Replacement of Carbon with Silicon (用硅对碳进行等电排置换)in the Design of Safer Chemicals ⚫ 4.2 Designing Biodegradable Chemicals ⚫ 4.3 Designing Aquatically Safer Chemicals ⚫ References

4.1 Isosteric Replacement of Carbon with Silicon (用硅对碳进行等 电排置换)in the Design of Safer Chemicals

4.1 Isosteric Replacement of Carbon with Silicon (用硅对碳进行等 电排置换)in the Design of Safer Chemicals

Silicon is an Isostere of Carbon Differences between Silicon compounds and Carbon compounds The degradation and oxidative metabolism of organic silicon compounds Examples of isosteric replacement of carbon with silicon for the design of safer chemicals

Silicon is an Isostere of Carbon Differences between Silicon compounds and Carbon compounds The degradation and oxidative metabolism of organic silicon compounds Examples of isosteric replacement of carbon with silicon for the design of safer chemicals

四川大学化学学院 2002年7月26日 5 4.1.1 Silicon is an Isosteric atom of Carbon Common Features of Silicon and Carbon ◼ grouped in column 4A of the Periodic Table ◼ having many chemical similarities ： tetravalent, tetrahedral, and form stable bonds with carbon. ◼ 金刚石 碳化硅

四川大学化学学院 2002年7月26日 5 4.1.1 Silicon is an Isosteric atom of Carbon Common Features of Silicon and Carbon ◼ grouped in column 4A of the Periodic Table ◼ having many chemical similarities ： tetravalent, tetrahedral, and form stable bonds with carbon. ◼ 金刚石 碳化硅

4.1.1 Silicon is an Isosteric atom of Carbon Organic derivatives of silicon and carbon generally have no intrinsic toxicity, in contrast with the other Group 4A elements germanium, tin, and lead. From a toxicity perspective, silicon is the only Group 4A element that is a suitable replacement for carbon. In addition, silicon is an abundant, inexpensive element and one that is available in a variety of forms

4.1.1 Silicon is an Isosteric atom of Carbon Organic derivatives of silicon and carbon generally have no intrinsic toxicity, in contrast with the other Group 4A elements germanium, tin, and lead. From a toxicity perspective, silicon is the only Group 4A element that is a suitable replacement for carbon. In addition, silicon is an abundant, inexpensive element and one that is available in a variety of forms

四川大学化学学院 2002年7月26日 7 The lifetime of organic silicon compounds is quite limited Insecticide (杀虫剂) Example Urethanes(尿烷), neutral analogs of the neuro-transmitter(神 经传递质)acetylcholine(乙酰胆碱)(1), were found to be antagonists(拮抗药)of (1) with identical dose-response curves . Interestingly, silane was much less toxic to mice than Urethane(carbon), and exhibited muscle relaxant properties

四川大学化学学院 2002年7月26日 7 The lifetime of organic silicon compounds is quite limited Insecticide (杀虫剂) Example Urethanes(尿烷), neutral analogs of the neuro-transmitter(神 经传递质)acetylcholine(乙酰胆碱)(1), were found to be antagonists(拮抗药)of (1) with identical dose-response curves . Interestingly, silane was much less toxic to mice than Urethane(carbon), and exhibited muscle relaxant properties

Acetylcholine(乙酰 胆碱) Urethane(尿烷) Muscarinic Antagonistis（ 蝇覃碱拮抗剂） O NH2 N O CH3 Si O NH2 O O O

Acetylcholine(乙酰 胆碱) Urethane(尿烷) Muscarinic Antagonistis（ 蝇覃碱拮抗剂） O NH2 N O CH3 Si O NH2 O O O

O NHCH3 O O NHCH3 Si O Carbamate Silicon substituted Isostere of carbamate (More degradable, less toxic to human and environment) Carbamate insecticide and its silicon analog were found to have similar toxicity to the house fly

O NHCH3 O O NHCH3 Si O Carbamate Silicon substituted Isostere of carbamate (More degradable, less toxic to human and environment) Carbamate insecticide and its silicon analog were found to have similar toxicity to the house fly

四川大学化学学院 2002年7月26日 10 ◼ In both of these examples, the tert￾butyl and trimethylsilyl groups function simply as isosteres of trimethylammonium

四川大学化学学院 2002年7月26日 10 ◼ In both of these examples, the tert￾butyl and trimethylsilyl groups function simply as isosteres of trimethylammonium