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The methylene group in diphenylmethane is mildly acidic with a pK a of 32.2, and so can be deprotonated with sodium amide. [3] (C 6 H 5) 2 CH 2 + NaNH 2 − → (C 6 H 5) 2 CHNa + NH 3. The resulting carbanion can be alkylated. For example, treatment with n-bromobutane produces 1,1-diphenylpentane in 92% yield. [4]
Ball-and-stick model of diphenylmethane. The benzhydryl compounds are a group of organic compounds whose parent structures include diphenylmethane (which is two benzene rings connected by a single methane), with any number of attached substituents, including bridges.
The bisphenols (/ ˈ b ɪ s f ɪ n ɒ l /) are a group of industrial chemical compounds related to diphenylmethane; commonly used in the creation of plastics and epoxy resins. [1] [2] [3] Most are based on two hydroxyphenyl functional groups linked by a methylene bridge.
Methylene diphenyl diisocyanate (MDI) is an aromatic diisocyanate. Three isomers are common, varying by the positions of the isocyanate groups around the rings: 2,2′-MDI, 2,4′-MDI, and 4,4′-MDI. The 4,4′ isomer is most widely used, and is also known as 4,4′-diphenylmethane diisocyanate. [3] This isomer is also known as Pure MDI.
Steric effects however prevent all three phenyl rings from achieving coplanarity simultaneously. Consequently diphenylmethane is even more acidic, albeit only slightly, because in its anion the charge is spread over two phenyl rings at the same time. The trityl anion is isolable in crown ethers: Its sodium salt can be prepared from the chloride ...
It is used in the synthesis of modafinil [4] and the benzhydryl group is present in the structure of many histamine H1 antagonists like diphenylhydramine. Benzhydrol is also used in the production of agrochemicals as well as other organic compounds and as a terminating group in polymerizations .
The group may be represented as −CH 2 − or >CH 2, where the '>' denotes the two bonds. This stands in contrast to a situation where the carbon atom is bound to the rest of the molecule by a double bond, which is preferably called a methylidene group, represented =CH 2. [2] Formerly the methylene name was used for both isomers.
These compounds are active in the cleavage of the RNA model compound HPNP. Substitution of the methylene group of the parent diphenylmethane spacer with cyclohexylidene and adamantylidene moieties enhances catalytic efficiency, with gem dialkyl effect accelerations of 4.5 and 9.1, respectively.