Sulfides, for example, react with alkyl halides to give ternary sulfonium salts (equation # 1) in the same manner that 3º-amines are alkylated to quaternary ammonium salts. R–S (–) Na (+) + (CH 3) 2CH–Br (CH 3) 2CH–S–R + Na (+) Br (–)Īlthough the basicity of ethers is roughly a hundred times greater than that of equivalent sulfides, the nucleophilicity of sulfur is much greater than that of oxygen, leading to a number of interesting and useful electrophilic substitutions of sulfur that are not normally observed for oxygen. Thiolate conjugate bases are easily formed, and have proven to be excellent nucleophiles in S N2 reactions of alkyl halides and tosylates. Since hydrogen sulfide (H 2S) is a much stronger acid than water (by more than ten million fold), we expect, and find, thiols to be stronger acids than equivalent alcohols and phenols. The chemical behavior of thiols and sulfides contrasts with that of alcohols and ethers in some important ways. Sulfur analogs of alcohols are called thiols or mercaptans, and ether analogs are called sulfides. All rights reserved.Sulfur and Phosphorus Compounds 1. On behalf of the United States of America. Shall not be liable for any damage that may result fromįor NIST Standard Reference Data products. However, NIST makes no warranties to that effect, and NIST Uses its best efforts to deliver a high quality copy of theĭatabase and to verify that the data contained therein haveīeen selected on the basis of sound scientific judgment. The National Institute of Standards and Technology (NIST) Data from NIST Standard Reference Database 69:.Go To: Top, Reaction thermochemistry data, Referencesįree energy of reaction at standard conditionsĮnthalpy of reaction at standard conditionsĮntropy of reaction at standard conditions Heats of formaton of CH 3SCH 2I, the CH 3SCH 2 radical, and the pibond energy in CH 2S, Iodine catalyzed pyrolysis of dimethyl sulfide. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,Īn Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions,Ĭhem. Hydration of the Alkali Ions in the Gas Phase. Binding Energies of Li+ to pi - and n - Donor Bases, Intrinsic Acid - Base Properties of Molecules. Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. Heats of formation of liquid methyl sulfoxide and crystalline methyl sulfone at 18°, A reevaluation of the upper proton affinity range, Proton affinity ladders from variable-temperature equilibrium measurements. Peschke, M.,Ī Definitive Investigation of the Gas-Phase Two-Center Three-electron Bond in, +, and +: Therory and Experiment, Mutual Effects of Weak and Strong Ligands in Mixed Clusters,ĭeng, Y. The Ionic Hydrogen Bond and Ion Solvation. Gas phase chemistry of alpha-thio carbanions,Ĭan. Photoelectron Spectroscopy of Sulfur Ions, Go To: Top, Reaction thermochemistry data, Notes
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