Protic solvent

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Overview

In chemistry a protic solvent is a solvent that has a hydrogen atom bound to an oxygen as in a hydroxyl group or a nitrogen as in an amine group. More generally, any molecular solvent which contains dissociable H⁺, such as hydrogen fluoride, is called a protic solvent. The molecules of such solvents can donate an H⁺ (proton). Conversely, aprotic solvents cannot donate hydrogen.

Common characteristics of protic solvents:

• solvents display hydrogen bonding
• solvents have an acidic hydrogen (although they may be very weak acids)
• solvents are able to stabilize ions
  • cations by unshared free electron pairs
  • anions by hydrogen bonding

Examples are water, methanol, ethanol, formic acid, hydrogen fluoride and ammonia.

Polar aprotic solvents are solvents that share ion dissolving power with protic solvents but lack an acidic hydrogen. These solvents generally have high dielectric constants and high polarity.

Examples are dimethyl sulfoxide, dimethylformamide, dioxane and hexamethylphosphorotriamide, tetrahydrofuran.

Polar protic solvents are favorable for S_N1 reactions, while polar aprotic solvents are favorable for S_N2 reactions. Apart from solvent effects, polar aprotic solvents may also be essential for reactions which use strong bases, such as reactions involving Grignard reagents or n-butyllithium. If a protic solvent were to be used, the reagent would be consumed by a side reaction with the solvent.

References

• Loudon, G. Mark. Organic Chemistry 4th ed. New York: Oxford University Press. 2002. pg 317.

Cost Effectiveness of Protic solvent

| group5 = Clinical Trials Involving Protic solvent | list5 = Ongoing Trials on Protic solvent at Clinical Trials.gov • Trial results on Protic solvent • Clinical Trials on Protic solvent at Google

| group6 = Guidelines / Policies / Government Resources (FDA/CDC) Regarding Protic solvent | list6 = US National Guidelines Clearinghouse on Protic solvent • NICE Guidance on Protic solvent • NHS PRODIGY Guidance • FDA on Protic solvent • CDC on Protic solvent

| group7 = Textbook Information on Protic solvent | list7 = Books and Textbook Information on Protic solvent

| group8 = Pharmacology Resources on Protic solvent | list8 = AND (Dose)}} Dosing of Protic solvent • AND (drug interactions)}} Drug interactions with Protic solvent • AND (side effects)}} Side effects of Protic solvent • AND (Allergy)}} Allergic reactions to Protic solvent • AND (overdose)}} Overdose information on Protic solvent • AND (carcinogenicity)}} Carcinogenicity information on Protic solvent • AND (pregnancy)}} Protic solvent in pregnancy • AND (pharmacokinetics)}} Pharmacokinetics of Protic solvent •

| group9 = Genetics, Pharmacogenomics, and Proteinomics of Protic solvent | list9 = AND (pharmacogenomics)}} Genetics of Protic solvent • AND (pharmacogenomics)}} Pharmacogenomics of Protic solvent • AND (proteomics)}} Proteomics of Protic solvent

| group10 = Newstories on Protic solvent | list10 = Protic solvent in the news • Be alerted to news on Protic solvent • News trends on Protic solvent</small>

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| group12 = Patient Resources on Protic solvent | list12 = Patient resources on Protic solvent • Discussion groups on Protic solvent • Patient Handouts on Protic solvent • Directions to Hospitals Treating Protic solvent • Risk calculators and risk factors for Protic solvent

| group13 = Healthcare Provider Resources on Protic solvent | list13 = Symptoms of Protic solvent • Causes & Risk Factors for Protic solvent • Diagnostic studies for Protic solvent • Treatment of Protic solvent

| group14 = Continuing Medical Education (CME) Programs on Protic solvent | list14 = CME Programs on Protic solvent

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| group16 = Business Resources on Protic solvent | list16 = Protic solvent in the Marketplace • Patents on Protic solvent

| group17 = Informatics Resources on Protic solvent | list17 = List of terms related to Protic solvent

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