Nicotine
“Nicotine and other tobacco alkaloids that possess a basic pyrrolidine nitrogen readily
form stable salts with both mineral and organic acids.” (Analytical Determination of
Nicotine and Related Compounds and Their Metabolites)
“Nicotine reacts with hydrochloric acid to form a water-soluble salt called nicotine
hydrochloride.” (General, Organic, and Biochemistry: An Applied Approach)
“Nicotine is a Diprotic Base with pKa's of 3.12 (pyridine ring) and 8.02 (pyrrolidine ring).”
(Optimization Study for the Reversed-Phase Ion-Pair Liquid Chromatographic
Determination of Nicotine in Commercial Tobacco Products)
The Nicotine Molecule contains two Nitrogen Atoms capable of accepting a Proton
The Pyrrolidine Nitrogen is considerably more basic than the Pyridine Nitrogen
Nitrogen Lone Electron Pairs form Coordinate (Dative) Covalent Bonds with Protons
Titration of Nicotine with HCl Titrant
Nicotine-2HCl
Nicotine-HCl
Nicotine
Nicotine Dissociation in Water
C10H14N2 + H2O C10H15N2+ + OHC10H15N2+ + H2O C10H16N22+ + OHHydrochloric Acid Dissociation in Water
HCl + H2O H3O+ + ClNicotine Neutralization with Hydrochloric Acid
C10H14N2 + HCl C10H15N2+ + Cl- (Nicotine Hydrochloride Salt)
C10H15N2 + HCl C10H16N22+ + Cl- (Nicotine Dihydrochloride Salt)
Molar Masses (Molecular Weights)
Nicotine C10H14N2
Carbon Atoms: 10 x 12.0107 = 120.107
Hydrogen Atoms: 14 x 1.00794 = 14.11116
Nitrogen Atoms: 2 x 14.00674 = 28.01348
Molecular Weight = 162.23164
Hydrochloric Acid HCl
Hydrogen Atom = 1.00794
Chlorine Atom = 35.453
Molecular Weight = 36.46094
Dilution of Solution – M1V1 = M2V2
(Molarity 1 X Volume 1 = Molarity 2 X Volume 2)
Moles of HCl (Hydrochloric Acid) vs. Moles of Nicotine
1. 0.10N HCl Contains 0.1 Moles of HCl/Liter.
2. To Calculate Moles of HCl in 1 ml of 0.10N HCl:
0.10N HCl = 0.1 Moles HCl/Liter
1 ml = 0.001 Liter
0.001 Liter X 0.1 Moles = 0.0001 Moles
3. 0.0001 Moles of 0.10N HCl will Neutralize 0.0001 Moles of Nicotine.
4. 0.0001 Moles of Nicotine = 16.223 mg (162.23 X 0.0001 = .016223 Grams)
5. 1 ml of 0.10N HCl Neutralizes 1 ml of 16.223 mg/ml Nicotine.
Nicotine Oxidation
C10H14N2 + O2 CO2 + H2O + N2
Nicotine Oxidation Balanced Equation
2 C10H14N2 + 27 O2 20 CO2 + 14 H2O + 4 N
pH Scale (pH = -Log10 [H+])