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An Acid-Base Chemistry Example: Conversion of Nicotine
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Abstract
The current government interest in nicotine conversion by cigarette companies provides an example of acid-base chemistry that can be explained to students in the second semester of general chemistry. In particular, the conversion by ammonia of the +1 form of nicotine to the easier-to-assimilate free-base form illustrates the effect of pH on acid-base equilibrium. The part played by ammonia in tobacco smoke is analogous to what takes place when cocaine is "free-based".
Keywords (Audience):
First-Year Undergraduate / GeneralKeywords (Domain):
Public Understanding / OutreachKeywords (Subject):
Acids / BasesCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
Possible Role of Ammonia on the Deposition, Retention, and Absorption of Nicotine in Humans while Smoking†
Jeffrey I. SeemanChemical Research in Toxicology2007 20 (3), 326-343Possible Role of Ammonia on the Deposition, Retention, and Absorption of Nicotine in Humans while Smoking†
Jeffrey I. SeemanChemical Research in Toxicology2007 20 (3), 326-343This perspective presents an overview of the properties of tobacco smoke aerosol and the possible effect of ammonia on the deposition location, retention and the amount and rate of nicotine absorption during cigarette smoking. Three main mechanisms ...
Using "Basic Principles" To Understand Complex Science: Nicotine Smoke Chemistry and Literature Analogies
Jeffrey I. SeemanJournal of Chemical Education2005 82 (10), 1577Using "Basic Principles" To Understand Complex Science: Nicotine Smoke Chemistry and Literature Analogies
Jeffrey I. SeemanJournal of Chemical Education2005 82 (10), 1577The Henderson–Hasselbalch equation calculates the equilibrium distribution of 50:50 for nicotine in its nonprotonated (free base form), relative to its monoprotonated form, at pH of 8 in dilute aqueous solution. This ratio has then been used in the ...
The Acid-Base Chemistry of Nicotine: Extensions, Analogies, and a Generalization
Addison AultJournal of Chemical Education2001 78 (4), 500The Acid-Base Chemistry of Nicotine: Extensions, Analogies, and a Generalization
Addison AultJournal of Chemical Education2001 78 (4), 500Some solutes can exist in aqueous solution in more than one form. Nicotine is an example of such a solute, as are amino acids and other substances that can exist in more than one state of ionization in water. This paper shows how to express the fractional ...
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- Received: August 03, 2009
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