Diphenylmethane2
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Diphenylmethane2
Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated ). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid. Diphenylmethane is a common skeleton in organic chemistry. The diphenylmethyl group is also known as ''benzhydryl''. Synthesis It is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as aluminium chloride: :C6H5CH2Cl + C6H6 → (C6H5)2CH2 + HCl Reactivity of the C-H bond The methylene group in diphenylmethane is mildly acidic with a p''K''a of 32.2, and so can be deprotonated with sodium amide. :(C6H5)2CH2 + NH2− → (C6H5)2CH− + NH3 The resulting carbanion can be alkylated. For example, treatment with ''n''-bromobutane produces 1,1-diphenylpentane in 92% yield. :(C6H5)2CH− + CH3CH2CH2CH2Br → (C6H5)2CHCH2CH2CH2CH3 + Br− Alkylation of various benzhydryl compounds has been demonst ...
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Benzhydryl
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. This group typically excludes compounds in which either benzene is fused to another ring (bicyclic, tricyclic, polycyclic) or includes a heteroatom, or where the methane connects to three or four benzenes. The benzhydryl ''radical'' can be abbreviated or Bzh. Carboaromatic Alcohols *''Acyclic:'' pridinol *''Pyrolidino:'' diphenylprolinol *''2-Piperidine:'' pipradrol *''4-Piperidine:'' terfenadine, fexofenadine *''Benzilic ester:'' QNB, JB-336, JB-318, benactyzine Alkenes *''Tricycle:'' amitriptyline, melitracen, cyclobenzaprine, tianeptine, amineptine, clopenthixol, chlorprothixene, flupentixol, thiothixene, zuclopenthixol *''Tricyclic and piperidine:'' pimethixene, cyproheptadine *''Acyclic:'' gilutensin Alkyl(amine)s *''Acyclic:'' (3-phenylpropyla ...
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Benzhydryl Compounds
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. This group typically excludes compounds in which either benzene is fused to another ring (bicyclic, tricyclic, polycyclic) or includes a heteroatom, or where the methane connects to three or four benzenes. The benzhydryl ''radical'' can be abbreviated or Bzh. Carboaromatic Alcohols *''Acyclic:'' pridinol *''Pyrolidino:'' diphenylprolinol *''2-Piperidine:'' pipradrol *''4-Piperidine:'' terfenadine, fexofenadine *''Benzilic ester:'' QNB, JB-336, JB-318, benactyzine Alkenes *''Tricycle:'' amitriptyline, melitracen, cyclobenzaprine, tianeptine, amineptine, clopenthixol, chlorprothixene, flupentixol, thiothixene, zuclopenthixol *''Tricyclic and piperidine:'' pimethixene, cyproheptadine *''Acyclic:'' gilutensin Alkyl(amine)s *''Acyclic:'' (3-phenylpropyla ...
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Benzhydryl Compounds
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. This group typically excludes compounds in which either benzene is fused to another ring (bicyclic, tricyclic, polycyclic) or includes a heteroatom, or where the methane connects to three or four benzenes. The benzhydryl ''radical'' can be abbreviated or Bzh. Carboaromatic Alcohols *''Acyclic:'' pridinol *''Pyrolidino:'' diphenylprolinol *''2-Piperidine:'' pipradrol *''4-Piperidine:'' terfenadine, fexofenadine *''Benzilic ester:'' QNB, JB-336, JB-318, benactyzine Alkenes *''Tricycle:'' amitriptyline, melitracen, cyclobenzaprine, tianeptine, amineptine, clopenthixol, chlorprothixene, flupentixol, thiothixene, zuclopenthixol *''Tricyclic and piperidine:'' pimethixene, cyproheptadine *''Acyclic:'' gilutensin Alkyl(amine)s *''Acyclic:'' (3-phenylpropyla ...
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International Union Of Pure And Applied Chemistry
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is a member of the International Science Council (ISC). IUPAC is registered in Zürich, Switzerland, and the administrative office, known as the "IUPAC Secretariat", is in Research Triangle Park, North Carolina, United States. This administrative office is headed by IUPAC's executive director, currently Lynn Soby. IUPAC was established in 1919 as the successor of the International Congress of Applied Chemistry for the advancement of chemistry. Its members, the National Adhering Organizations, can be national chemistry societies, national academies of sciences, or other bodies representing chemists. There are fifty-four National Adhering Organizations and three Associate National Adhering Organizations. IUPAC's Inter-divisional Committee on ...
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University Of California, Berkeley
The University of California, Berkeley (UC Berkeley, Berkeley, Cal, or California) is a public land-grant research university in Berkeley, California. Established in 1868 as the University of California, it is the state's first land-grant university and the founding campus of the University of California system. Its fourteen colleges and schools offer over 350 degree programs and enroll some 31,800 undergraduate and 13,200 graduate students. Berkeley ranks among the world's top universities. A founding member of the Association of American Universities, Berkeley hosts many leading research institutes dedicated to science, engineering, and mathematics. The university founded and maintains close relationships with three national laboratories at Berkeley, Livermore and Los Alamos, and has played a prominent role in many scientific advances, from the Manhattan Project and the discovery of 16 chemical elements to breakthroughs in computer science and genomics. Berkeley is ...
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Accounts Of Chemical Research
''Accounts of Chemical Research'' is a semi-monthly peer-reviewed scientific journal published by the American Chemical Society containing overviews of basic research and applications in chemistry and biochemistry. It was established in 1968 and the editor-in-chief is Cynthia J. Burrows (University of Utah). Abstracting and indexing The journal is abstracted and indexed in: According to the ''Journal Citation Reports'', the journal has a 2020 impact factor The impact factor (IF) or journal impact factor (JIF) of an academic journal is a scientometric index calculated by Clarivate that reflects the yearly mean number of citations of articles published in the last two years in a given journal, as i ... of 22.384. References External links * {{American Chemical Society Journals Chemical Research Publications established in 1968 Monthly journals English-language journals ...
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Toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent. As the solvent in some types of paint thinner, permanent markers, contact cement and certain types of glue, toluene is sometimes used as a recreational inhalant and has the potential of causing severe neurological harm. History The compound was first isolated in 1837 through a distillation of pine oil by the Polish chemist Filip Walter, who named it ''rétinnaphte''. In 1841, French chemist Henri Étienne Sainte-Claire Deville isolated a hydrocarbon from balsam of Tolu (an aromatic extract from the tropical Colombian tree ''Myroxylon balsamum''), which Deville recognized as similar to Wa ...
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Propane
Propane () is a three-carbon alkane with the molecular formula . It is a gas at standard temperature and pressure, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used as a fuel in domestic and industrial applications and in low-emissions public transportation. Discovered in 1857 by the French chemist Marcellin Berthelot, it became commercially available in the US by 1911. Propane is one of a group of liquefied petroleum gases (LP gases). The others include butane, propylene, butadiene, butylene, isobutylene, and mixtures thereof. Propane has lower volumetric energy density, but higher gravimetric energy density and burns more cleanly than gasoline and coal. Propane gas has become a popular choice for barbecues and portable stoves because its low −42 °C boiling point makes it vaporise inside pressurised liquid containers (2 phases). Propane powers buses, forklifts, taxis, outboard boat motors, and ic ...
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Bond Dissociation Energy
The bond-dissociation energy (BDE, ''D''0, or ''DH°'') is one measure of the strength of a chemical bond . It can be defined as the standard enthalpy change when is cleaved by homolysis to give fragments A and B, which are usually radical species. The enthalpy change is temperature-dependent, and the bond-dissociation energy is often defined to be the enthalpy change of the homolysis at 0  K (absolute zero), although the enthalpy change at 298 K (standard conditions) is also a frequently encountered parameter. As a typical example, the bond-dissociation energy for one of the C−H bonds in ethane () is defined as the standard enthalpy change of the process : , : ''DH''°298() = Δ''H°'' = 101.1(4) kcal/mol = 423.0 ± 1.7 kJ/mol = 4.40(2)  eV (per bond). To convert a molar BDE to the energy needed to dissociate the bond ''per molecule'', the conversion factor 23.060 kcal/mol (96.485 kJ/mol) for each eV can be used. A variety of experim ...
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Isopropyl Chloride
Isopropyl chloride is an organic compound with the chemical formula (CH3)2CHCl. It is a colourless to slightly yellow, volatile, flammable liquid with a sweet, ether-like (almost like petroleum) odour. It is used industrially as a solvent. It is produced industrially by the addition of HCl to propylene: :CH3CH=CH2 + HCl → (CH3)2CHCl Isopropyl chloride can be easily produced in the lab by reacting concentrated hydrochloric acid with isopropyl alcohol in the presence of a calcium chloride or zinc chloride catalyst. The common ratio of alcohol to acid to catalyst is 1:2:1 using 30% HCl and near pure isopropanol. The reaction mixture is refluxed for several hours, or distilled over several hours. The isopropyl chloride is then separated from the remaining isopropyl alcohol by washing with water (the isopropyl chloride will form in insoluble layer above the water, while the alcohol will dissolve into solution along with any HCl present). In the presence of a catalyst, dr ...
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