Chemical Properties of Proline (CAS 147-85-3)

InChI

InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1

InChI Key

ONIBWKKTOPOVIA-SCSAIBSYSA-N

Formula

C5H9NO2

SMILES

O=C(O)C1CCCN1

Molecular Weight¹

115.13

CAS

147-85-3

Other Names

• (+)-(R)-proline
• (-)-(S)-Proline
• (R)-2-carboxypyrrolidine
• (S)-2-PYRRALIDINECARBOXYLIC ACID
• (S)-2-pyrrolidinecarboxylic acid
• 2-Pyrrolidinecarboxylic acid
• 2-Pyrrolidinecarboxylic acid, (S)-
• D-proline
• L-(-)-Proline
• L-PROLINE
• Proline, L-
• R-proline

• PAff : Proton affinity (kJ/mol).
• BasG : Gas basicity (kJ/mol).
• Δ_cH°_solid : Standard solid enthalpy of combustion (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• C_p,solid : Solid phase heat capacity (J/mol×K).
• Δ_fG° : Standard Gibbs free energy of formation (kJ/mol).
• Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
• Δ_fH°_solid : Solid phase enthalpy of formation at standard conditions (kJ/mol).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_subH° : Enthalpy of sublimation at standard conditions (kJ/mol).
• Δ_subH : Enthalpy of sublimation at a given temperature (kJ/mol).
• Δ_vapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
• IE : Ionization energy (eV).
• log₁₀WS : Log10 of Water solubility in mol/l.
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• P_c : Critical Pressure (kPa).
• P_vap : Vapor pressure (kPa).
• S°_{solid,1 bar} : Solid phase molar entropy at standard conditions (J/mol×K).
• T_boil : Normal Boiling Point Temperature (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• V_c : Critical Volume (m³/kmol).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
PAff	[920.10; 938.90]	kJ/mol
PAff	920.50	kJ/mol	NIST
PAff	925.90 ± 1.60	kJ/mol	NIST
PAff	936.00	kJ/mol	NIST
PAff	920.10	kJ/mol	NIST
PAff	938.90	kJ/mol	NIST
BasG	[886.00; 895.70]	kJ/mol
BasG	886.00	kJ/mol	NIST
BasG	895.70 ± 1.60	kJ/mol	NIST
ΔcH°solid	[-2746.20; -2738.60]	kJ/mol
ΔcH°solid	-2746.20 ± 2.50	kJ/mol	NIST
ΔcH°solid	-2738.60 ± 0.40	kJ/mol	NIST
ΔfG°	-150.26	kJ/mol	Joback Calculated Property
ΔfH°gas	-366.20 ± 4.00	kJ/mol	NIST
ΔfH°solid	[-515.18; -507.60]	kJ/mol
ΔfH°solid	-507.60 ± 2.60	kJ/mol	NIST
ΔfH°solid	-515.18 ± 0.52	kJ/mol	NIST
ΔfusH°	17.92	kJ/mol	Joback Calculated Property
ΔsubH°	149.00 ± 2.00	kJ/mol	NIST
ΔvapH°	57.16	kJ/mol	Joback Calculated Property
IE	[8.30; 9.36]	eV
IE	8.30	eV	NIST
IE	9.36	eV	NIST
IE	9.00	eV	NIST
log10WS	-0.21		Crippen Calculated Property
logPoct/wat	-0.177		Crippen Calculated Property
McVol	87.870	ml/mol	McGowan Calculated Property
Pc	5585.83	kPa	Joback Calculated Property
S°solid,1 bar	[164.06; 170.70]	J/mol×K
S°solid,1 bar	164.06	J/mol×K	NIST
S°solid,1 bar	170.70	J/mol×K	NIST
Tboil	523.68	K	Joback Calculated Property
Tc	729.91	K	Joback Calculated Property
Tfus	372.79	K	Joback Calculated Property
Vc	0.319	m3/kmol	Joback Calculated Property

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[201.66; 255.23]	J/mol×K	[523.68; 729.91]
T(K) Ideal gas heat capacity (J/mol×K) 200 210 220 230 240 250 260 550 600 650 700
Cp,gas	201.66	J/mol×K	523.68	Joback Calculated Property
Cp,gas	211.92	J/mol×K	558.05	Joback Calculated Property
Cp,gas	221.63	J/mol×K	592.42	Joback Calculated Property
Cp,gas	230.81	J/mol×K	626.80	Joback Calculated Property
Cp,gas	239.45	J/mol×K	661.17	Joback Calculated Property
Cp,gas	247.59	J/mol×K	695.54	Joback Calculated Property
Cp,gas	255.23	J/mol×K	729.91	Joback Calculated Property
Cp,solid	[149.12; 151.17]	J/mol×K	[298.15; 300.40]
Cp,solid	150.40	J/mol×K	298.15	NIST
Cp,solid	151.17	J/mol×K	298.15	NIST
Cp,solid	149.12	J/mol×K	300.40	NIST
ΔsubH	[96.70; 149.00]	kJ/mol	[400.00; 455.00]
ΔsubH	149.00 ± 4.00	kJ/mol	400.00	NIST
ΔsubH	127.00 ± 1.00	kJ/mol	406.00	NIST
ΔsubH	96.70 ± 0.80	kJ/mol	455.00	NIST

Correlations

Property	Value	Unit	Temperature (K)	Source
Pvap	[9.52; 42.66]	kPa	[441.15; 466.15]	KDB Vap...
Equation			ln(Pvp) = A + B/T + C*ln(T) + D*T^2
Coefficient A			3.00080e+01
Coefficient B			-1.23246e+04
Coefficient C			3.09086e-02
Coefficient D			-2.47929e-08
Temperature range, min.			441.15
Temperature range, max.			466.15
T(K) Vapor pressure (kPa) 10 15 20 25 30 35 40 45 450 460
Pvap	9.52	kPa	441.15	Calculated Property
Pvap	11.35	kPa	443.93	Calculated Property
Pvap	13.49	kPa	446.71	Calculated Property
Pvap	15.99	kPa	449.48	Calculated Property
Pvap	18.93	kPa	452.26	Calculated Property
Pvap	22.36	kPa	455.04	Calculated Property
Pvap	26.36	kPa	457.82	Calculated Property
Pvap	31.01	kPa	460.59	Calculated Property
Pvap	36.41	kPa	463.37	Calculated Property
Pvap	42.66	kPa	466.15	Calculated Property

Similar Compounds

Find more compounds similar to Proline.

Mixtures

• Proline + Water
• Proline + Carbon dioxide
• Proline + Norflurane
• potassium chloride + Proline + Water
• Potassium nitrate + Proline + Water
• Proline + Water + Potassium sulfate
• Proline + sodium chloride + Water
• Proline + Sodium nitrate + Water
• Ammonium sulfate + Proline + Water
• Proline + Pentanoic acid, 4-oxo-
• Proline + Lactic acid
• Proline + Ethanol + Water
• Proline + Ethanol
• Proline + Methyl Alcohol
• Proline + Acetone
• Proline + Acetonitrile
• Proline + Acetone + Methyl Alcohol
• Proline + Ethanol + Acetone
• Proline + Acetonitrile + Methyl Alcohol
• Proline + Acetonitrile + Ethanol

Find more mixtures with Proline.

Sources

• KDB Vapor Pressure Data
• Crippen Method
• Crippen Method
• Effect of KCl and KNO3 on Partial Molal Volumes and Partial Molal Compressibilities of Some Amino Acids at Different Temperatures
• Volumetric and viscometric behaviour of amino acids in aqueous metal electrolytes solutions at 308K
• Salting-out effect in polypropylene glycol-amino acid aqueous solutions revealed by vapor pressure osmometry
• Vapor pressure osmometry determination of vapor-liquid equilibria behavior of aqueous imidazolium-based ionic liquid + amino acid systems
• Intermolecular/interionic interactions in L-isoleucine-, L-proline-, and L-glutamine-aqueous electrolyte systems
• Viscosity studies of (L-alanine-, L-proline, L-valine, L-leucine + aqueous KCl/KNO3) solutions at different temperatures
• Thermodynamic properties of aqueous 4-hydroxyproline at different temperatures
• Activity coefficients of CaCl2 in (serine or proline + water) mixtures at T = 298.15 K
• Measuring and modeling aqueous electrolyte/amino-acid solutions with ePC-SAFT
• Study of the interactions of PAMAM-NH2 G4 dendrimer with selected natural amino acids in aqueous solutions
• Effect of temperature on solvation behaviour of diclofenac sodium salt in aqueous glycine and L-proline solutions
• Volumetric and compressibility behaviour of poly(propylene glycol) - Amino acid aqueous solutions at different temperatures
• Volumetric property of glycine, L-serine, L-alanine and L-proline in aqueous solutions of 1-phenylpiperazinium tetrafluoroborate
• Physical properties of seven deep eutectic solvents based on L-proline or betaine
• Volumetric approach to the interaction of L-Proline in aqueous Metformin Hydrochloride solutions for temperature range 298.15-318.15 K
• Interactions in l-alanine /l-proline /l-valine /l-leucine aqueous KCl/KNO3 systems at different temperatures: An isentropic compressibility study
• THE STANDARD ENTHALPIES OF FORMATION OF PROLINE ISOMERS
• Solubility of the Proteinogenic a-Amino Acids in Water, Ethanol, and Ethanol-Water Mixtures
• Surface Tension of Aqueous Solutions of Small-Chain Amino and Organic Acids
• Temperature of Maximum Density for Binary Aqueous Solutions of Five Amino Acids
• Solubility Behavior and Data Modeling of l-Proline in Different Neat and Binary Solvent Systems
• Mutual Coexistence Curve Measurement of Aqueous Biphasic Systems Composed of [bmim][BF4] and Glycine, L-Serine, and L-Proline, Respectively
• Viscosities of l-Phenylalanine, l-Leucine, l-Glutamic Acid, or l-Proline + 2.0 mol*dm-3 Aqueous NaCl or 2.0 mol*dm-3 Aqueous NaNO3 Solutions at T = (298.15 to 328.15) K
• Densities, Speeds of Sound, and Viscosities of (L-Proline + Aqueous Glucose), and (L-Proline + Aqueous Sucrose) Solutions in the Temperature Range (298.15 to 323.15) K
• Solubility and Thermodynamic Properties of (2S)-Pyrrolidine-2-carboxylic Acid in Water, Alcohols, and Water Alcohol Mixtures
• Temperature Dependences and Enthalpic Discrimination of Homochiral Pairwise Interactions of Six a-Amino Acid Enantiomers in Pure Water
• Solubilities of L-Proline in Subcritical HFC-134a and Supercritical CO2 Fluids
• Ultrasonic Velocities and Densities of l-Phenylalanine, l-Leucine, l-Glutamic Acid, and l-Proline + 2 mol*L-1 Aqueous NaCl and 2 mol*L-1 Aqueous NaNO3 Solutions from (298.15 to 328.15) K
• Joback Method
• KDB
• McGowan Method
• NIST Webbook

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