Dave's Molecular Models
Acids (organic)

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File revised: Thu, Mar 27, 2014 .

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Tutorials: Beginning Organic Chemistry. | Organic Nomenclature | Problem Solving

The following molecular models are part of Dave's molecular models database.

Note: The model presentation uses the Jmol applet requiring Java to be installed on your computer.

Model files copyright 1994-2004, 2005

The models may be used for educational or personal purposes, but may not be copied for publishing use without permission of the author.

Name (click for model)Comments
CH2O246.03Methanoic acid, Formic acidpKa 3.75
CH2O362.03Carbonic acidUnstable relative to CO2 and H2O."
C2H2O490.04Ethanedioic acid, Oxalic acidpKa values: 1.23, 4.19. Found in rhubarb leaves.
C2H3BrO2138.95Bromoethanoic acidpKa=2.86"
C2H3ClO294.5Chloroethanoic acid,
chloroacetic acid
Sodium salt is monoxone."
C2H3FO277.05Fluoroethanoic acidpKa=2.66"
C2H3IO2185.96Iodoethanoic acidpKa=3.15"
C2H4O260.06Ethanoic acid,
Acetic acid
pKa 4.75.
Vinegar is an approx. 5% solution."
C3H2O386.05Deltic acidpKa1 : 2.5
pKa2 : 6.0"
C3H2O5118.05Oxopropanedioic acidFound in beet molasses."
C3H4O4104.07Propanedioic acid, Malonic acid"
C3H4O5120.072-Hydroxypropandioic acid"
C3H5BrO2152.98(S)-2-Bromopropanoic acid"
C3H5BrO2152.98(R)-2-Bromopropanoic acid"
C3H5ClO2108.533-Chloropropanoic acidpKa 4.0"
C3H5NO4119.09HadacidinAntitumor antibiotic properties"
C3H6BrO2153.99(S)-2-Bromopropanoic acid"
C3H6BrO2153.99(R)-2-Bromopropanoic acid"
C3H6O274.09Propanoic acid"
C3H6O390.09(R)-2-Hydroxypropanoic acidLactic acid"
C3H6O390.09(S)-(+)-Lactic AcidIn blood and muscles of man and animals."
C3H7NO289.11AlanineAmino acid"
C3H7NO2S121.17(R)-CysteineNatural enantiomer, L-"
C4H2O4114.06Squaric acidpKa1 : 0.5
pKa2 : 3.5"
C4H4O4116.08trans-Butenedioic acidFumaric acid. Pka 3.03 and 4.44."
C4H4O4116.08cis-Butenedioic acidMaleic acid. pKa 1.83 and 6.07."
C4H6O286.1(E)-But-2-enoic acidCrotonic acid. pKa 4.7"
C4H6O286.1(Z)-But-2-enoic acid"
C4H6O5134.1Hydroxybutanedioic acid(S)-Malic acid, apple acid. Found in many fruits."
C4H6O6150.1(+)-(2R,3R)-Tartaric Acidby-product of wine making, see the S,S enantiomer"
C4H6O6150.1(2R,3S)-Tartaric Acid (meso)"
C4H6O6150.1(-)-(2S,3S)-Tartaric Acida rare form of this acid with no optical rotation was called Racemic Acid (from "+ "racemus=bunch of grapes, L). Experiment showed that this was a 50-50 mixture of the (+) and (-) forms of tartaric acid (which were separated by hand-picking crystals of the sodium ammonium salt of racemic acid) and this has led all such 50-50 mixtures of the two enantiomers being labelled racemic"
C4H7BrO2167.012-Bromo-2-methylpropanoic acid"
C4H8O288.12Butanoic acidThe smell of rancid butter"
C5H2O5142.07Croconic acidpKa1 : 0.8
pKa2 : 2.2"
C5H4O3112.092-Furoic acid"
C5H6O4130.11Itaconic acidUsed in the production od adhesives and paints.
Pka 3.85; 5.45
C5H6O4130.11(E)-2-Methylbutenedioic acidPka 3.07; 5.82"
C5H8O2100.13(Z)-2-Methylbut-2-enoic acidAngelic acid
pKa 4.3"
C5H8O2100.13(E)-2-Methylbut-2-enoic acidTiglic acid
pKa 5.02"
C5H8O2100.13(R)-2-Methylbut-3-enoic acid"
C5H8O2100.13(S)-2-Methylbut-3-enoic acid"
C5H8O2100.13(Z)-2-Methylbut-2-enoic acidAngelic acid: found in sumbul root, Angelica archangelica L., as an ester."
C5H8O3116.134-Oxopentanoic acidLevulinic acid, used in the manufacture of nylon, plastics and rubbers."
C5H9BrO2181.04(R)-2-Bromo-3-methylbutanoic acid"
C5H9BrO2181.04(S)-2-Bromo-3-methylbutanoic acid"
C5H9BrO2181.043-Bromo-3-methylbutanoic acid"
C5H9BrO2181.04(R)-2-Bromopentanoic acidpKa=2.97"
C5H9BrO2181.04(S)-2-Bromopentanoic acidpKa=2.97"
C5H9BrO2181.04(R)-3-Bromopentanoic acidpKa=4.01"
C5H9BrO2181.04(S)-3-Bromopentanoic acidpKa=4.01"
C5H9BrO2181.04(R)-4-Bromopentanoic acidpKa=4.59"
C5H9BrO2181.04(S)-4-Bromopentanoic acidpKa=4.59"
C5H9BrO2181.045-Bromopentanoic acidpKa=4.71"
C5H9ClO2136.59(S)-3-Chloropentanoic acid"
C5H10O2102.15(S)-2-Methylbutanoic acid"
C5H10O2102.15Pentanoic acid"
C6H2O6170.08Rhodizonic acid"
C6H3N3O7229.12Picric acidexplosive - care!"
C6H6O6174.12Aconitic acidFrom leaves and tubers of Aconitum napellus.
Plasticizer in form of triethyl or tributyl esters."
C6H9N3O2155.18HistidineAmino acid"
C6H10O2114.16(Z)-Hex-2-enoic acid"
C6H10O4146.16Hexanedioic acidNylon precursor"
C6H11BrO2195.07(2R,3R)-2-Bromo-3-methylpentanoic acid"
C6H11BrO2195.07(2S,3S)-2-Bromo-3-methylpentanoic acid"
C6H11ClO2150.62(2R,4R)-2-Chloro-4-hydroxyhexanoic acid"
C6H13NO2131.26-Aminohexanoic acid"
C7HCl5O2294.33Pentachlorobenzoic acid"
C7H3Br3O2358.82,4,6-Tribromobenzoic acid"
C7H5IO2248.033-Iodobenzoic acid"
C7H5NO4167.132-Nitrobenzoic acid"
C7H5NO4167.134-Nitrobenzoic acid"
C7H6O2122.13Benzoic acidfound in gum benzoin and in most berries, salts used as preservative"
C7H6O5170.133,4,5-Trihydroxybenzoic acidGallic acid: found in gallnuts, sumach, tea leaves, oak bark, and many other plants, both in its free state and as part of the tannin molecule"
C7H7NO2137.153-Aminobenzoic acid"
C7H7NO2137.152-Aminobenzoic acidvitamin L1, anthranilic acid"
C7H7NO2137.154-Aminobenzoic acidPABA. Sometimes used in sun screen lotions."
C7H12O2128.19Cyclohexanecarboxylic acidEquatorial, chair."
C7H14O2130.213-Ethylpentanoic acid"
C7H14O2130.213-Ethylpentanoic acid"
C7H14O2130.21Heptanoic acidpKa 4.85"
C7H15NO3161.23(3S,4R)-4-Amino-3-hydroxy-7-oxoheptanoic acid"
C8H5Cl3O2239.482,3,6-Trichlorophenylethanoic acidFenac, a herbicide.
C8H6O4166.14Phthalic acid"
C8H6O4166.14Isophthalic acidm-Phthalic acid."
C8H6O4166.14Terephthalic acidp-Phthalic acid."
C8H8O2136.163-Toluic acid"
C8H8O3152.164-Methoxybenzoic acid,
p-anisic acid
C8H14O2142.22(Z)-Oct-5-enoic acid"
C8H16O2144.24(S)-3-Ethylhexanoic acid"
C8H16O2144.24(R)-3-Ethylhexanoic acid"
C8H16O2144.246-Methylheptanoic acid"
C8H16O2144.24Octanoic acid"
C8H16O3160.24(2R,4R)-2-Ethyl-4-hydroxyhexanoic acid"
C8H16O3160.24(2S,4S)-2-Ethyl-4-hydroxyhexanoic acid"
C8H17NO3S207.32FelinineIsolated from cat urine. Rotation: -11.5"
C9H8O4180.17Acetylsalicylic Acidaspirin, asa
analgesic, antipyretic, anti-inflammatory information
The Aspirin story"
C9H10NO5212.25-Ethoxy-3-nitrobenzoic acid"
C9H11NO3181.21TyrosineL- (S) enantiomer is naturally occuring amino acid."
C9H16O4188.25(R)-6-Hydroxy-4-oxononanoic acid"
C9H18O2158.27(S)-2-Isopropyl-4-methylpentanoic acid"
C9H18O2158.27(R)-2-Isopropyl-4-methylpentanoic acid"
-3-hydroxy-7-oxoheptanoic acid
C10H12O2164.222,4,6-Trimethylbenzoic acid"
C10H16136.26D-Lactic acidRacemic lactic acid occurs in sour milk."
C10H16O2168.26(+)-trans-Chrysanthemic acida terpene constituent of Chrysanthemum cinerariifolium"
C10H16O3184.26(E)-9-Oxodec-2-enoic acidQueen substance of honey bee, Apis mellifera"
C10H17N3O6S307.36GlutathioneMajor small sulphur-containing molecule in living plants and animals.
Biochemical roles."
C10H18O2170.28(Z)-Dec-3-enoic acidSex pheromone of the furniture carpet beetle, Anthrenus flavipes."
C10H18O3186.28(E)-9-Hydroxydec-2-enoic acidComponent of swarm-setting pheromone of queen honeybees."
C10H20O2172.3Decanoic acid"
C11H8N2O3S248.27LuciferinIsolated from the American firefly. 15,000 fireflies gives 9 mg.
Simple description plus other refs"
C11H14O2178.255-Phenylpentanoic acid"
C12H24O2200.36Dodecanoic acidLauric acid, from coconut and other oils.
All about coconuts!"
C13H18O2206.31IbuprofenAdvil, Motrim: anti-inflammatory.
drug database
also here."
-3-nitrobenzoic acid
Chiral because the groups on the benzene ring cannot pass each other. Called: atropisomerism"
-3-nitrobenzoic acid
Chiral because the groups on the benzene ring cannot pass each other. Called: atropisomerism"
C14H14O3230.28(S)-NaproxenNaproxen is a chiral, nonsteroidal anti-inflammatory drug with analgesic and antipyretic properties.
C14H15NO7309.3LaetrileRise and fall of Laetrile."
C14H18N2O5294.34AspartameNutrasweet, a synthetic, non-nutrative sweetener"
C15H11I4NO4776.91Levothyroxineas sodium salt: Synthroid, for treatment of hyperthyroidism.
Thyroid desease references"
C15H14ClN3O4S367.83CefaclorCeclor, an semisynthetic antibiotic.
WWW guide to cephalosporins
also : How to take cephalosporins"
Yellow #5
Lemon yellow food colouring (trianion).
C16H18N2O4S334.42Penicillin G"
C16H19N3O5S365.44AmoxicillinAmoxil, an semisynthetic antibiotic related to penicillin.
WWW description"
C18H32O2280.5(11E,9Z)-Octadeca-9,11-dienoic acid"
C18H32O2280.5(10E,12Z)-Octadeca-10,12-dienoic acid"
C18H32O2280.5(9Z,12Z)-Octadeca-9,12-dienoic acidPresent in many vegetable oils. Used in paints, emulsifiers."
Vernolic acid: principle seed oil acid from Vernonia anthelmintica"
C18H34O2282.52Oleic acid"
C18H36O2284.54Octadecanoic acid, Stearic acid"
C19H12O6336.31DicoumarolIn spoiled sweet clover, used as an anticoagulant."
C19H19N7O6441.45Folic acid (folate)Vitamin"
C19H22O6346.41Gibberellic acidPlant hormone - most potent of the growth promoting metabolites of Gibberella fujikuroi. Used as a plant growth regulator, especially for seedlings, and as a food additive in the malting of barley."
C19H36O2296.55Lactobacillic acidConstituent of microorganisms."
Red #3
Cherry red food colouring (dianion).
C20H22N8O5454.5MethotrexateBlocks the effect of folic acid (q.v.)
C20H25N3O323.48LSDlysergic acid, diethylamide, a potent hallucinogen"
C20H28N2O5376.5Enalapril(Vasotec). An antihypertensive.
WWW reference."
C20H40280.6Eicosanoic acidArachidic acid, found in a number of oils including peanut oil."
C22H42O2338.64(E)-Docos-13-enoic acidBrassidic acid."
C22H42O2338.64(Z)-Docos-13-enoic acidErucic acid. 40-50% of the fatty acids in seeds such as rapeseed and mustard."
Web site
More information
Crystals photograph"
C24H40O5408.64(+)Cholic acida bile acid.
11 stereocentres lead to 2048 possible stereoisomers. Of the these only this one is found naturally."
C34H32FeN4O4616.55HemeIn hemoglobin in the blood."
C36H61NaO11692.96Monensin - Sodium saltAn ionophore antibiotic produced by the bacteria Streptoyces cinnamonensis. Used in beef cattle to increase the weight gain to food intake ratio.
C36H62O11670.98MonensinAn ionophore antibiotic produced by the bacteria Streptoyces cinnamonensis. Used in beef cattle to increase the weight gain to food intake ratio.
Number of entries in table : 149

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This page last modified on: Thu, Mar 27, 2014 .