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The alkyl derivatives of many metals undergo protonolysis. For the alkyls of very electropositive metals (zinc, magnesium, and lithium), water is sufficiently acidic, in which case the reaction is called hydrolysis. Protonolysis with mineral acids is sometimes used to remove organic ligands from a
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since the reaction requires polar M-R bonds, where δ+ and δ- signify partial positive and negative charges associated with the bonding atoms. When compounds containing these bonds are treated with acid (HX), these bonds cleave:
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Inorganic materials with highly charged anions are often susceptible to protonolysis. Derivatives of nitride (N), phosphides (P), and silicides (Si) hydrolyze to give
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Chu Sun, Masami Okabe, David L. Coffen, Jeffrey
Schwartz "Conjugate Addition Of A Vinylzirconium Reagent: 3-(1-octen-1-yl)cyclopentanone".Org. Synth. 1993, 71, 83.
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Gordon W. Gribble, Ahmed F. Abdel-Magid, "Sodium
Triacetoxyborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007, John Wiley & Sons.
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anion is susceptible to reaction with even weak acids, resulting protonolysis of one or more B-H bonds. Protonolysis of sodium borohydride with
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Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the
Elements (2nd Edn.), Oxford:Butterworth-Heinemann.
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42:(X = OH) is a special case of protonolysis. Compounds susceptible to hydrolysis often undergo protonolysis.
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Related reactions occur for hydrides of other electropositive elements, e.g.
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Nitrides, phosphides, silicides and related species
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16:Cleavage of a chemical bond by acids
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99:lithium aluminium hydride
180:10.15227/orgsyn.071.0083
28:organometallic chemistry
60:triacetoxyborohydride
22:is the cleavage of a
35:M-R + HX → M-X + H-R
216:Chemical reactions
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138:, and M-SiR
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146:References
40:Hydrolysis
124:phosphine
210:Category
78:→ NaBH(O
46:Hydrides
142:bonds.
120:ammonia
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128:silane
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105:Alkyls
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58:gives
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