Related Experiment Video
Updated: Jun 2, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Mechanistic considerations of guanidine-catalyzed reactions
1Department of Chemistry, 3 Science Drive 3, National University of Singapore, Singapore 117543.
Abstract:
This feature article discusses the various mechanistic aspects of guanidine-catalyzed reactions. Guanidines are well known as strong organic bases; however, in the first section, three most common commercially available guanidines, TMG, TBD and MTBD, will be used to illustrate the use of guanidines as nucleophilic catalysts. In the second section, different modes of hydrogen bonding interactions of the conjugate acid of guanidine, the guanidinium, are discussed. Particularly interesting are the possibilities of mono-functional or bifunctional activation of a nucleophile and an electrophile by guanidinium.
Related Concept Videos
Introduction to Mechanisms of Enzyme Catalysis
Introduction to Mechanisms of Enzyme Catalysis
Rate-Determining Steps
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...
Multi-Step Reactions
Catalysis
Catalysis

