N,N,N′,N′-Tetramethylformamidinium Chloride
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N,N,N′,N′-Tetramethylformamidinium Chloride
''N'',''N'',''N''′,''N''′-Tetramethylformamidinium chloride is the simplest representative of quaternary formamidinium cations of the general formula + with a chloride as a counterion in which all hydrogen atoms of the protonated formamidine C(=NH2)NH2sup>+ are replaced by methyl groups. Deprotonation results in the exceptionally basic bis(dimethylamino)carbene R2N−C̈−NR2. Preparation It is generated by protonation of (CH3)3COCH(N(CH3)2)2 ( Bredereck's reagent). :(CH3)3COCH(N(CH3)2)2 + H+ → (CH3)3COH + H(N(CH3)2)2sup>+ ''N'',''N'',''N''′,''N''′-Tetramethylformamidinium chloride is also obtained in high yield (95%) in the reaction of dimethylformamide (DMF) with dimethylcarbamoyl chlorideThe conversion of DMF with thionyl chloride in a ratio of 3:1 obtains the product in a is significantly lower yield (72%) which appears, however, more realistic in view of the tricky handling of the chloride salt. : Properties ''N'',''N'',''N''′,''N''′-Tetrameth ...
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An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convention. The net charge of an ion is not zero because its total number of electrons is unequal to its total number of protons. A cation is a positively charged ion with fewer electrons than protons while an anion is a negatively charged ion with more electrons than protons. Opposite electric charges are pulled towards one another by electrostatic force, so cations and anions attract each other and readily form ionic compounds. Ions consisting of only a single atom are termed atomic or monatomic ions, while two or more atoms form molecular ions or polyatomic ions. In the case of physical ionization in a fluid (gas or liquid), "ion pairs" are created by spontaneous molecule collisions, where each generated pair consists of a free electron and ...
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