Organometallic Chemistry

26 Jun 2020

Evans' Method Calculator

Submitted by Bradley Wile, Ohio Northern University
Description: 

A spreadsheet hosted on Pete Wolczanski's webpage for calculating (mu)effective

Topics Covered: 
Prerequisites: 
Course Level: 
Corequisites: 
Implementation Notes: 

Use this mainly for inorganic lab (Mn(acac)3) and my research group.

10 Jun 2020

A copper "Click" catalyst for the synthesis of 1,2,3-triazoles

Submitted by Chip Nataro, Lafayette College
Evaluation Methods: 

I have not used this in class yet, but anticipate updating this after the fall 2020 semester. This comes as a result of the June 9th LO party.

Description: 

This paper (Gayen, F.R.; Ali, A.A.; Bora, D.; Roy, S.; Saha, S.; Saikia, L.; Goswamee, R.L. and Saha, B. Dalton Trans2020, 49, 6578) describes the synthesis, characterization and catalytic activity of a copper complex with a ferrocene-containing Schiff base ligand. The article is relatively short but packed with information. However, many of the details that are assumed knowledge in the article make for wonderful questions some of which I hope I have captured. The LO includes electron counting using the CBC method, d-orbital splitting, Latimer diagrams and interpretation of catalytic results. There are also opportunities to discuss green chemical practices.

Corequisites: 
Prerequisites: 
Course Level: 
Learning Goals: 

A student should be able

determine the electro count and metal valence in the catalyst

use group theory to determine the number of IR active vibrations in the catalyst

discuss green chemical principles in relation to this article

interpret data from tables and draw conclusions from that data

suggest an additional catalytic experiment that could be performed

Implementation Notes: 

I like the question invoking a Latimer Diagram to get students to rationalize why the copper(I) active catalyst was not isolated. I also enjoyed sneaking in a group theory question. But my favorite quesiton is the last one in which students are asked to go beyond what it presented in the paper and suggest another catalytic reaction to perform. There are some aspects of the paper that were not covered in-depth. In particular the XPS seemed to be a rabbit hole I opted not to go down. The authors do not go into great detail on this topic and perhaps there is a question that could be included, but I opted not to. I also opted not to include anything about the bonding in ferrocene which can be found in many of my other LOs. Also on this list one might include UV-Vis spectroscopy and the computational studies.

Time Required: 
50 minutes
18 May 2020
Evaluation Methods: 

I have not yet implemented this LO. As with other literature discussions, instructors could collect the completed worksheets (by an individual student or in groups of students) for evaluation.

Evaluation Results: 

I have not yet implemented this LO so there are currently no evaluation results to share.

 

 

Description: 

This literature discussion focuses upon the Science article by Coates and Waymouth reporting the synthesis of thermoplastic elastomeric polypropylene by an unbridged zirconocene. This article was the basis for the work done for my PhD thesis in the Waymouth group. The LO was written in May 2020 in honor of Bob Waymouth's 60th birthday. See the BITeS post announcing the LO here

Course Level: 
Corequisites: 
Subdiscipline: 
Learning Goals: 

After completing this literature discussion, students will be able to:

  • describe a thermoplastic elastomer
  • describe the stereochemistry of polypropylene
  • describe the relationship between catalyst structure and polypropylene stereochemistry
  • apply covalent bond classification electron counting to a zirconocene
  • interpret data from figures and tables
  • describe the methods used by the authors to support the synthesis of isotactic-atactic stereoblock polypropylene
Implementation Notes: 

As usual, instructors may wish to mix-and-match questions to suit their learning goals and time constraints.

This article addresses a part of the ACS list of inorganic chemistry macromolecular, supramolecular and nanoscale (MSN) topics:

  • Ziegler-Natta, metallocene catalysts for olefin polymerization - impact on industrial/materials development
Time Required: 
depends upon implementation; minimum of 20-30 minutes for the literature discussion if students read and answer questions outside of class
15 May 2020

Inorganic Active Learning Lesson Plan Design

Submitted by Meghan Porter, Indiana University
Evaluation Methods: 

I use the rubric provided, combined with the peer review feedback (due to COVID, they did not have the chance to revise after the peer review process).  Students must also upload a key with their activity which allows me to catch any misconceptions or inaccuracies in their understanding of the material.

I assigned points as following:

Assignment/Key: See above rubric

Reflection: Worth 5 points total- while mostly graded on completion, I did want to be sure my students were providing more useful feedback than 1 word answers so I gave them the rubric below. (pretty much everyone got a 5)

Completed Reflection

5

3

1

What did you learn from completing this assignment? (i.e. What do you feel that you gained from completing it?)

What did you learn from completing other students' assignments?

What are your thoughts for improving the active learning lesson plan assignment in future iterations?  You may answer this referring to your specific lesson plan or this actual assignment of creating a lesson plan.

 

Meets all criteria at a high level, all questions are thoughtfully addressed

Meets some criteria, some questions are not addressed or non-thoughtful response provided

Meets few criteria, most questions not addressed or responses do not demonstrate thought

Peer Review: Spring 2020 was my first time doing the peer review, and of course covid definitely changed the way I had planned on completing it.  My plan was to have them exchange activities in class or in recitation, work through them in small groups, then be able to provide feedback.  Instead, they had to complete it online and provide feedback- I gave them the basic rubic, but changed the scores to categories of "exceeds expectations", "meets expectations", and "does not meet expectations".

Evaluation Results: 

I am always blown away by the creativity of my students!  While some students submit more group worksheet activities, I have had plenty come up with games, relays, building/using playdough, etc...

Students usually report that they thought they knew a topic- only to begin making an activity and realize they didn't understand it as well as they thought they did.  However, by the time the submitted their activity, they felt like they gained a much more in-depth understanding.  They also loved getting to complete other students' assignments this semester.  Their feedback indicated that they felt it was a great way to review, but also get some insight into how their peers think differently about topics.

Side note: Personally, I love seeing how many students tell me afterward that they have a newfound respect for professors after trying to make their own activity! :-)

Description: 

I created this activity as a way to get the class involved in creating new, fun ways to teach course concepts (selfishly- that part is for me) and for students to review concepts prior to the final exam (for them).  Students use a template to create a 15-20 min activity that can be used in groups during class to teach a concept we have learned during the semester.  We then randomly assign the activities and students work in groups to complete them and provide feedback.

The benefits are twofold:

1. My class is about 100-150 students per semester.  This means that each semester I have a large number of new activities (that I didn't have to make!) to use as a starting point in future semesters as I work to create a more active classroom.

2. The students get a review of the topic they have chosen for their activity, plus, they get to review additional topics from completing and providing feedback on two activities from their peers.

I have run this assignment for three semesters now.  It has been a favorite of my students since the beginning!  I have received a number of activities that I now use in class to teach topics!

Learning Goals: 

A student should be able to

  • Create a lesson plan on an inorganic topic that incorporates active learning
  • Demonstrate understanding of chosen topic via an accurate lesson plan key
  • Review multiple inorganic topics through completion of lesson plans from classmates
  • Provide constructive feedback on classmates’ completed lesson plans

 

Equipment needs: 

None

Corequisites: 
Prerequisites: 
Implementation Notes: 

Since this can be used for any level or any topic, there are plenty of variations you can try!  Some things to consider:

1. You can allow students to select any topic from the entire semester for their activity- this can be helpful prior to a final exam when you want a comprehensive review.  You can also restrict topics if you have areas that you feel your students need to focus on or if you want to assign this before a specific exam.  One of my students also suggested having a sign up sheet for topics on a first-come, first-served basis so that you don't end up with 20 balancing redox reactions and zero crystal field splitting.

2. I have tried students designing plans individually and also working in partners to create acitivties (both outside of class).  Both methods worked well, but in a class of 150, that many individual submissions to grade was a bit overwhelming!

3. The peer review was new this semester (based on a previous student suggestion).  My original plan was have them use a recitation section to work in groups through randomly assgined activities.  Due to COVID, they completed the activites on their own- they enjoyed it, but the group experience would ave been more fun.

4. Depending on your timing, you could have them go through the peer review process and then give them a chance to revise the activity based on the feedback prior to you grading it.

5. The student reflection questions are given as a survey on Canvas after they have completed both the lesson plan and the peer review process.

6 Apr 2020

Schlenk Line Survival guide

Submitted by Adam R. Johnson, Harvey Mudd College
Evaluation Methods: 

This is really more of a resource. I have not used it but I have a link to it in my reserach SOP folder. I think it would be good to show the students a general resource before teaching them the specifics of a local line.

Description: 

I feel like I've shared this resource before but I couldn't find it so maybe it will stick this time :)

This is a good resource created by "Dr. Andryj Borys, a main-group chemist, phosphorus fanatic and Schlenk line enthusiast." He is currently a postdoc in Canada, headed back to Europe in 2020 (supposedly..)

this resource describes the use of a Schlenk line in quite a bit of detail, with a variety of standard applications (cannula transfer, sealing NMR tubes).

Topics Covered: 
Prerequisites: 
Corequisites: 
Course Level: 
Learning Goals: 

A student can use this resource to learn general features of a Schlenk line.

6 Apr 2020

Migratory Insertion Guided inquiry

Submitted by Adam R. Johnson, Harvey Mudd College
Evaluation Methods: 

I look to see if students are able to 

1) determine the correct number of IR stretches for the compounds,

2) calculate the labeled IR stretches from the unlabeled ones,

3) correctly predict the product distributions expected for the 3 mechanistic pathways

4) understand/explain the importance of experiment 2, negative evidence, and microscopic reversibility

Evaluation Results: 

Awaiting assessment data at time of submission; will add ASAP.

based on 3 complete submissions (43% response rate, due to COVID)

students generally had no problems with questions 1 and 2, and were able to determine the number/symmetry of IR stretches using group theory, and to predict a vibrational frequency from a areduced mass calculation.

question 3 gave them a lot of trouble. I would normally do this as an in-class exercise and be able to talk them thorugh problems. students were able to draw some of the correct products for the various mechanisms but did not understand the fact that there would be a statistical distribution of products based on the 13C label. However, I spoke with all 3 students and they said that after priming their brains with the exercise, the reading in the textbook made a lot of sense and they understood what they had missed. Perfect!

Students did not generally understand the concept of negative evidence as hoped.

For future years, if I were unable to do this exercise in class, I would want to provide more guidance to get students to think about product distribution. However, if done in class, I think that watching them struggle a bit before helping them over the hurdle would be good.

Description: 

The migratory insertion reaction is one of the "four" main reactions in organometallic chemistry. It involves the formation of an acyl group by insertion of a CO molecule into a metal alkyl bond. The reaction is sometimes called the carbonyl insertion reaction because the product appears to be a result of direct insertion of the CO into the metal alkyl, but that name implies a mechanistic pathway that may not be in operation.

The reaction of methyl pentacarbonyl manganese(I), MeMn(CO)5, was studied extensively by Calderazzo in the mid 1960s. The use of C13 labeled CO and IR spectroscopy allowed for the identification of the mechanism for the reaction among the likely possibilities of direct insertion, alkyl migration, or carbonyl migration. This guided inquiry exercise presents some of the data from the Calderazzo paper and has students interpret it to determine the mechanism of the reaction in this system.

It should be noted that there are examples of all three mechanisms operating in different chemical systems, so this exercise is specific to the manganese substrate, though it is usually more generally applied.

Learning Goals: 

Students will interpret and analyze IR data of metal carbonyls

Students will calculate IR bands for 13C labeled peaks in the IR

Students will predict product distributions for the three likely mechanisms (direct insertion, carbonyl migration, alkyl migration).

Students will compare expected and observed product distributions and identify the mechanism operating

Students will discover and discuss the concept of "negative evidence."

Equipment needs: 

none

Prerequisites: 
Corequisites: 
Subdiscipline: 
Course Level: 
Implementation Notes: 

In my course, we usually cover isotopic labeling and its application to IR spectroscopy. We also use group theoretical methods to predict and assign M-CO stretches the correct symmetry labels and whether they are IR active or not. These two factors could be removed from the guided inquiry and presented as additional data to the students if you don't cover these topics. The rest of the activity is self contained. Access to the paper is not required, as the IR bands are in the document but a reference is provided.

Time Required: 
30-50 minutes
26 Mar 2020
Evaluation Methods: 

Student learning is assessed by answers to simple scenario based questions accompanying this resouce.

Description: 

One of the features of the laboratory associated with my Inorganic chemistry course is learning to do some air sensitive chemistry using Schlenk lines (and sometimes gloveboxes).  Of course, COVID19 is keeping us out of the lab this year!  This is a collection of short web based resources (text and video) detailing begining use of a Schlenk line, something about drying and degassing solvents, and transferring liquids to a reaction flask.  It is accompanied by questions I am having students answer as part of the alternate lab I am creating in place of our usual organometallic lab experiemnt.  If you have a favorite resource that might be better/supplement the ones I found, please add to the comments!

Prerequisites: 
Corequisites: 
Course Level: 
Learning Goals: 

A student will be able to explain the basic operation of a Shlenk line and how to add reagents and solvents to a flask under inert atmosphere.

Time Required: 
2 hours, if all videos are watched and resources read.
21 Mar 2020

chromium and molybdenum arene complexes (COVID-19 version)

Submitted by Adam R. Johnson, Harvey Mudd College
Evaluation Methods: 

i have no idea.... yet! (growth mindset!)

Evaluation Results: 

I will report this later this spring.

Description: 

The synthesis of (arene)Cr(CO)3 and (arene)Mo(CO)3 complexes are fairly standard experiments in the organometallic curriculum. I present here some student data and experimental descriptions of real procedures carried out at Harvey Mudd College over the previous two to three years. The word document has the answers in it so it is posted under "faculty resources" but the raw data (pdf or png form) is presented for those who need data to support their distance learning classrooms in the Spring of 2020. I also include an input file for Mo(benzene)(CO)3 should you desire to use WebMO or Gaussian to carry out some calculations. 

 

there was a minor mistake in the reported integrations for one of the complexes in the original faculty only file; it has been fixed in the v2 version.

Course Level: 
Prerequisites: 
Corequisites: 
Learning Goals: 

Students will interpret provided data to write their own experimental sections for molecules they were unable to prepare in the lab. The guided inquiry part allows students to use data to predict the outcome of a chemical reaction.

Equipment needs: 

be able to view PDF/PNG files

Implementation Notes: 

I have not used this yet but will be using it spring 2020.

Time Required: 
unknown
21 Mar 2020

Ferrocene acylation - The Covid-19 Version

Submitted by Chip Nataro, Lafayette College
Description: 

This is the classic Chromatography of Ferrocene Derivatives experiment from "Synthesis and Technique in Inorganic Chemistry" 3rd Ed. (1986 pp 157-168) by R. J. Angelici. There are no significant changes from the experiment published in the book so details will not be provided. What is provided are links to some excellent videos showing the experiment and characterization data for students to work with. For the time being this will be a living document. Currently it has 1H, 13C{1H}, COSY, DEPT, HMBC, HSQC IR, UV-Vis, GC-MS and Cyclic Voltammetry raw data files for all compounds for students to work with. It also includes processed 1H, 13C{1H}, COSY, DEPT, HMBC, HSQC, IR, GC-MS and Cyclic Voltammetry data for all compounds. If anyone has any additional means of characterization they would like to include (say Mossbauer) please feel free to contact the author.

Corequisites: 
Learning Goals: 

A student should get an appreciation for what doing this lab would be like by watching videos. In addition, the student will analyze the data provided and learn about the characterization of ferrocene, acetylferrocene and 1,1'-diacetylferrocene.

Equipment needs: 

Nothing.

The NMR data comes from a Bruker instrument and can be opened with TopSpin, MestReNova and perhaps other programs.

Implementation Notes: 

Like most everyone at this time this is going to be a trial by fire.

20 Mar 2020

setting up an air-sensitive reaction (video)

Submitted by Adam R. Johnson, Harvey Mudd College
Evaluation Methods: 

have not done

Evaluation Results: 

n/a

Description: 

This is a video I made to demonstrate the basics of air-sensitive reaction setup under nitrogen flush. It is the simplest, most basic method for setting up a reaction with air/water sensitive reagents.

The link goes to my channel on YouTube.

Corequisites: 
Subdiscipline: 
Learning Goals: 

After watching this video, a student will be able to set up a reaction under nitrogen. Or, if there is a global pandemic and the students are at home, they will at least see how it is done.

Course Level: 
Implementation Notes: 

I made this and am sharing it with my students because they did not get an opportunity to set up an air sensitive reaction this year.

Time Required: 
5 minutes to watch video

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