Introduction of a Computational Chemistry Course-Based Undergraduate Research Experience (CURE) into an Advanced Organic Chemistry Lab: An Investigation of Propellane Formation

Phillip J. Alexander¹, Dillon Button-Jennings¹, Claudia N. Evans¹, Mason B. Hemstreet¹, Marissa E. Henager¹, Stephanie Jacob¹, Charles S. Jolly¹, Maayan R. Lantzman¹, Alexandra Saputo¹, Nolan R. Stager¹, Elizabeth L. Whitman¹, Bohdi J. Young¹ and Gary W. Breton^1,

¹Department of Chemistry and Biochemistry, Berry College, Mount Berry GA, USA

Cite this paper

Phillip J. Alexander, Dillon Button-Jennings, Claudia N. Evans, Mason B. Hemstreet, Marissa E. Henager, Stephanie Jacob, Charles S. Jolly, Maayan R. Lantzman, Alexandra Saputo, Nolan R. Stager, Elizabeth L. Whitman, Bohdi J. Young and Gary W. Breton. Introduction of a Computational Chemistry Course-Based Undergraduate Research Experience (CURE) into an Advanced Organic Chemistry Lab: An Investigation of Propellane Formation. World Journal of Chemical Education. 2021; 9(3):88-93. doi: 10.12691/WJCE-9-3-4

Abstract

The introduction of basic computational chemistry concepts is becoming an integral part of any complete undergraduate curriculum in chemistry. The advanced organic chemistry course affords laboratory time in which some focused study of computational chemistry is possible. Although learning how to carry out basic computational manipulations is important, interest in computational chemistry can be instilled by carrying out a research-like experience. We incorporated a course-based undergraduate research experience (CURE) into our advanced organic chemistry lab course in which students, as a group, studied the spontaneous formation of strained propellane compounds from the corresponding anionic bridgehead bromide precursor compounds. Completing the calculations and data analysis as a class simulated a true research project, and led to the discovery of results from which interesting conclusions were drawn. Student feedback was generally very positive and suggested that this project gave them a strong sense for how computational chemistry research is conducted.

Keywords

organic chemistry, computational chemistry, propellanes, course-based research experience, CURE

Copyright

This work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

References

[1]	Esselman, B. J.; Hill, N. J. “Integrating Computational Chemistry into an Organic Chemistry Laboratory Curriculum Using WebMO”, In Using Computational Methods To Teach Chemical Principles; American Chemical Society, 2019; Vol. 1312, pp 139-162.
[2]	Esselman, B, J.; Hill, N. J. “Integration of Computational Chemistry into the Undergraduate Organic Chemistry Curriculum”, J. Chem. Ed. 2016, 93, 932-936.
[3]	Sharma, A. K.; DeCicco, R. C. “Discovering Isomerism: A Guided-Inquiry Computational Exercise for Undergraduate Organic Chemistry”, Chem. Educator 2018, 23, 39-41.
[4]	Ivey, M. M.; Slaughter, J.; Smith, Jr., R.; Ward, D. N.; Sonnenberg, J. L. “Computational Chemistry Experiments for an Organic Chemistry Course”, Chem. Educator 2021, 26, 23-30.
[5]	Hirsh, H., Coen, M.H., Mozer, M.C., Hasha, R. and Flanagan, J.L, “Room service, AI-style,” IEEE intelligent systems, 14 (2). 8-19. Jul.2002.
[6]	Dinadayalane, T.; Bowen, N. J. “Computational Chemistry and Biology Courses for Undergraduates at an HBCU: Cultivating a Diverse Computational Science Community”, In Growing Diverse STEM Communities: Methodology, Impact and Evidence; American Chemical Society, 2019; Vol. 1328, pp 67-81.
[7]	Deveau, A. M.; Wang, Y.; Small, D. J. ”Reflections on Course-Based Undergraduate Research in Organic and Biochemistry during COVID-19”, J. Chem. Ed. 2020, 97, 3463-3469.
[8]	Cruz, C. L.; Holmberg-Douglas, N.; Onuska, N. P. R.; McManus, J. B.; MacKenzie, I. A.; Hutson, B. L.; Eskew, N. A.; Nicewicz, D. A. “Development of a Large-Enrollment Course-Based Research Experience in an Undergraduate Organic Chemistry Laboratory: Structure-Function in Pyrylium Photoredox Catalysts”, J. Chem. Ed. 2020, 97, 1572-1578.
[9]	Wiberg, K. B. ”Small-Ring Propellanes”, Chem. Rev. 1989, 89, 975-983.
[10]	Frisch. M. J. et al., Gaussian, Inc., Wallingford CT, 2016. https://gaussian.com/ (accessed October 29, 2021).
[11]	Barca, G. M. J. et al. “Recent Developments in the General Atomic and Molecular Electronic Structure System”, J. Chem. Phys. 2020, 152, 154102.
[12]	Neese, F. “Software Update: the ORCA Program System, Version 4.0”, Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2017, 8, e1327.
[13]	https://www.wavefun.com/spartan-student (accessed November 4, 2021).
[14]	Shao, Y. et al. “Advances in Methods and Algorithms in a Modern Quantum Chemistry Package”, Phys. Chem. Chem. Phys. 2006, 8, 3172-3191.
[15]	Perri, M. J.; Weber, S. H. “Web-Based Job Submission Interface for the GAMESS Computationsl Chemistry Program”, J. Chem. Ed. 2014, 91, 2206-2208.
[16]	Wiberg, K. B.; Epling, G. A.; Jason, M. “Electrochemical Reduction of 1,4-Dibromobicyclo[2.2.2]octane. Formation of the [2.2.2]Propellane”, J. Am. Chem. Soc. 1974, 96, 912-913.