What is triflate used for?
A triflate group is an excellent leaving group used in certain organic reactions such as nucleophilic substitution, Suzuki couplings and Heck reactions. Since alkyl triflates are extremely reactive in SN2 reactions, they must be stored in conditions free of nucleophiles (such as water).
What is OTf in organic chemistry?
Illustrated Glossary of Organic Chemistry – Triflate (trifluoromethanesulfonate; TfO) Trifluoromethanesulfonate (triflate; TfO; OTf): An ester or salt of trifluoromethanesulfonic acid (CF3SO3H).
What is 3so3?
Silver trifluoromethanesulfonate, or silver triflate is the triflate (CF3SO3−) salt of Ag+. It is a white or colorless solid that is soluble in water and some organic solvents including, benzene. It is a reagent used in the synthesis of organic and inorganic triflates.
Why is triflic acid so strong?
Its extreme acidity can be derived from the extreme amount of resonance between the sulfur and three oxygen atoms coupled with the extremely electron-withdrawing qualities of the fluorocarbon group. Triflic acid is also very effective because its conjugate base does not act as a nucleophile.
Which is better leaving group triflate or tosylate?
No. They are the best leaving groups, but there are other good leaving groups. Triflate, tosylate, and mesylate ions are excellent leaving groups, because the sulfonate ions can stabilize the negative charge via resonance. Good leaving groups are weak bases.
Is ts a good leaving group?
The tosylate group makes for an excellent leaving group and is commonly used in organic chemistry in a multitude of reactions. This is a most stabilizing effect and this is what makes the tosylate group such a good leaving group.
Whats does OTF mean?
OTF
| Acronym | Definition |
|---|---|
| OTF | One Time Fee |
| OTF | Off the Front (cycling/racing slang) |
| OTF | Open Trace Format |
| OTF | Over the Falls (surfing) |
Is mesylate a good leaving group?
Chlorides, bromides, and tosylate / mesylate groups are excellent leaving groups in nucleophilic substitution reactions, due to resonance delocalization of the developing negative charge on the leaving oxygen.
What does sulfuric acid look like?
Concentrated sulfuric acid is highly corrosive towards other materials, from rocks to metals, since it is an oxidant with powerful dehydrating properties….Sulfuric acid.
| Names | |
|---|---|
| Appearance | Clear, colorless liquid |
| Odor | Odorless |
| Density | 1.8302 g/cm3, liquid |
| Melting point | 10.31 °C (50.56 °F; 283.46 K) |
What is the pH of magic acid?
-23
Magic acid is a combination of three very strong acids, and it acts like it has a pH of -23. That’s a hundred billion times more powerful than pure sulfuric acid!
What’s the strongest acid in the world?
Fluoroantimonic acid
Fluoroantimonic acid is the strongest super-acid known in existence. It is 20 quintillion times more acidic than 100% sulfuric acid, and it can dissolve glass plus a host of other substances.
What is the most powerful base?
The title of strongest base in the world belongs to ortho-diethynylbenzene dianion. This superbase has the strongest proton affinity ever calculated (1843 kJ mol−1), beating out a long-standing contender known as lithium monoxide anion.
Which is the correct way to write triflate?
The triflate group is often represented by −OTf, as opposed to −Tf ( triflyl ). For example, n -butyl triflate can be written as CH 3 CH 2 CH 2 CH 2 OTf.
When to use a triflate as a leaving group?
A triflate group is an excellent leaving group used in certain organic reactions such as nucleophilic substitution, Suzuki couplings and Heck reactions. Since alkyl triflates are extremely reactive in S N 2 reactions, they must be stored in conditions free of nucleophiles (such as water).
How is the triflate group displaced from Silicon?
The triflate group is displaced very readily from silicon, the hydrolysis of silyl triflates occurring rapidly even in crowded molecules. For example, the silyl triflates (Me3 Si) 2 C (SiMe 2 CH═CH 2 ) (SiMe 2 OSO 2 CF 3) and (Me 3 Si) 3 CSiMe 2 OSO 2 CF 3 both react readily with 1% water in MeOH to give the corresponding silanols exclusively (17).
Which is the correct formula for triflate ion?
Triflate, also known by the systematic name trifluoromethanesulfonate, is a functional group with the formula CF 3 SO 3 −. The triflate group is often represented by −OTf, as opposed to −Tf ( triflyl ). For example, n -butyl triflate can be written as CH 3 CH 2 CH 2 CH 2 OTf.