This page makes use of JSmol to render molecules as an intractable object. This package has two modes: HTML5, and WEBGL. The first is slower and produces a lower quality rendering, but supports showing vibrations and is supported on more devices. Therefore, it has been chosen as the default rendering mode. To reload the page with WEBGL, click here, but note that all animations will be disabled.
It may take a few minutes for all of the components to load, so be patient! Note that Chrome and similar browsers will not respond until the page is fully loaded, so do not be alarmed if the page does not respond Intermediately! You can tell the page has finished loaded when benzene is displayed below:
If Web-based applications are too slow, please download the Gaussian16 output files and formatted checkpoint files, which are provided as links on this webpage and on the associated GitHub profile.
Starting material Interactions Transition States Intermediates Products
Below is the starting materials for the reaction. When summed together, the total ΔG is 0 as these reactants serve as the reference state for all other steps in the reaction.
Starting Sulfonylimine (Gaussian output and checkpoint)
Benzoic Acid (Gaussian output and checkpoint)
(N-Isocyanoimino)triphenylphosphorane (Gaussian output and checkpoint)
These are interaction structures formed between the reactants before a transition state can be formed.
Interaction between the starting material and (N-Isocyanoimino)triphenylphosphorane (Gaussian output and checkpoint)
Interaction between intermediate 1 and benzoic acid (Gaussian output and checkpoint)
Below are the four transition states for the reaction shown in an interactive JSmol applet. By default, the sole negative frequency is shown, but this can be turned off using the toggle links below the animation. Additional vibrations can be loaded by right clicking the application and selecting a different model.
Attack of (N-Isocyanoimino)triphenylphosphorane onto the Sulfonylimine
Gaussian output and checkpoint
Attack of the Carboxylic acid onto Intermediate-1
Gaussian output and checkpoint
Below are the intermediates for the reaction.
Intermediate 1 (Gaussian output and checkpoint)
Intermediate 2 (Gaussian output and checkpoint)
Intermediate 3 (Gaussian output and checkpoint)
Oxazaphosphetidine Intermediate (Gaussian output and checkpoint)
The products of the reaction are an oxadiazole and Ph3P=O.
The resulting oxadiazole (Gaussian output and checkpoint)
Ph3P=O (Gaussian output and checkpoint)