"Protic" redirects here. For the surname, see Protić.
In chemistry, a protic solvent is a solvent that has a hydrogen atom bound to an oxygen (as in a hydroxyl group −OH), a nitrogen (as in an amine group −NH2 or −NH−), or fluoride (as in hydrogen fluoride). In general terms, any solvent that contains a labile H+ is called a protic solvent. The molecules of such solvents readily donate protons (H+) to solutes, often via hydrogen bonding. Water is the most common protic solvent. Conversely, polar aprotic solvents cannot donate protons but still have the ability to dissolve many salts.[1][2]
Methods for purification of common solvents are available[3]
Solvent
Chemical formula
Boiling point
Dielectric constant
Density
Dipole moment (D)
Polar protic solvents
formic acid
HCO2H
101 °C
58
1.21 g/mL
1.41 D
n-butanol
CH3CH2CH2CH2OH
118 °C
18
0.810 g/mL
1.63 D
isopropanol (IPA)
(CH3)2CH(OH)
82 °C
18
0.785 g/mL
1.66 D
nitromethane [note 2]
CH3NO2
101°C
35.87
1.1371 g/mL
3.56 D
ethanol (EtOH)
CH3CH2OH
79 °C
24.55
0.789 g/mL
1.69 D
methanol (MeOH)
CH3OH
65 °C
33
0.791 g/mL
1.70 D
Acetic acid (AcOH)
CH3CO2H
118 °C
6.2
1.049 g/mL
1.74 D
Water
H2O
100 °C
80
1.000 g/mL
1.85 D
^Stoye, Dieter (2000). "Solvents". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437. ISBN 978-3527306732.
^John R. Rumble (ed.). "Laboratory Solvent Solvents and Other Liquid Reagents". CRC Handbook of Chemistry and Physics, 102nd Edition (Internet Version 2021). Boca Raton, FL, USA: CRC Press/Taylor & Francis.
^W. L. F. Armarego (2017). Purification of Laboratory Chemicals, 8th Edition. Elsevier. ISBN 9780128054567.
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aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents lack hydroxyl and amine groups. In contrast to proticsolvents, these...
changing from a proticsolvent to an aprotic solvent. This difference arises from acid/base reactions between proticsolvents (not aprotic solvents) and strong...
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reaction remains unchanged. Such autoionization can be protic (H+ transfer), or non-protic. Proticsolvents often undergo some autoionization (in this case autoprotolysis):...
water, and I− is a better nucleophile than Br− (in polar proticsolvents). In a polar aprotic solvent, nucleophilicity increases up a column of the periodic...
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accept H-bonds, donate H-bonds, or both. Solvents that can donate H-bonds are referred to as protic, while solvents that do not contain a polarized bond to...
reducing the material, conductive organic polymers associated with a proticsolvent may also be "self-doped." Undoped conjugated polymers are semiconductors...
it is used as a medium-polarity non-proticsolvent that is miscible with water and a range of organic solvents, but not saturated hydrocarbons. It has...
2-chloroethanol with sodium sulfide. Thiodiglycol is a polar proticsolvent. It is used as a solvent in a variety of applications ranging from dyeing textiles...
solvation sheath is the solvent interface of any chemical compound or biomolecule that constitutes the solute in a solution. When the solvent is water it is called...
the reaction. The normal solvents of choice are both polar (to stabilize ionic intermediates in general) and proticsolvents (to solvate the leaving group...
nucleophiles and good ligands. Alkoxides, although generally not stable in proticsolvents such as water, occur widely as intermediates in various reactions,...
nucleophiles. In polar, proticsolvents, F− is the weakest nucleophile, and I− the strongest; this order is reversed in polar, aprotic solvents. Carbon nucleophiles...
exposure to one- or two-electron reducing agents. In the presence of a proticsolvent, reduction stops at this stage to afford the monohalo ketone (which...
number is related to the broader concept of solvation number, the number of solvent molecules bonded to a central atom. The hydration number varies with the...
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