1. Jessica A. Thomas Department of Biology and Chemistry Purdue University North Central

2. Gloaguen, et al, J. Phys. Chem. B. (2013) 117, 4945 - 4955. FF_A FF_B FF_C

3. C5 C7 C10 T- or L-shaped V-shaped (approaching parallel)

4.  Dispersion correcting potentials are appended to Gaussian09 input files Torres and DiLabio, J. Phys. Chem. Lett. (2012) 3, 1738 – 1744. Revised values for carbon: DiLabio, Koleini, and Torres, Theor. Chem. Acc. (2013) 132, 1389. Gaussian Potentials applied to atoms:

5. FF: Three experimentally assigned conformersWY: One experimentally observed conformer  Analogous to FF_C FF_A FF_B FF_C WY_A

6. C10 C7 (terminal) C7/C7 C7 (mid) C7/C10C5/C7 C5 g+g+ All three have same low energy structure. Agrees with FF_A

7. FY YFFF FF, FY, and YF overlaid g+ C10

8. C7 (terminal) C7/C7 C7 (mid) C7/C10C5/C7 C5 g+g+ FF_B is identified FY has an analogous structure FF_A FF_B

9. FY FF FF_B and FF overlaid FF and FY overlaid

10. C10 C7 (terminal) C7/C7 C7 (mid) C7/C10C5/C7 C5 g+g+ FF_A FF_B Two versions of C5/C7: ag- = T/L-shaped ag+ = V-shaped g+g+ ag- ag+

11. Almost parallel rings ag- T/L-shaped rings C5 C7 FF_C and WY_A have ag+ configuration

12. C10 C7 (terminal) C7/C7 C7 (mid) C7/C10C5/C7 C5 g+g+ FF_A FF_B ag- ag+ FF_C (and WY_A) g-g- g+g- g-g+ g+g+ g+g- g+g+ g+g- ag+ g+g+ and g+g- g-g+, ag-, and ag+

14. C10 C7 (terminal) C7/C7 C7 (mid) C7/C10 C5/C7 C5 g+g+ FF_A FF_B ag- ag+ FF_C (and WY_A) g-g- g+g- g-g+ g+g+ g+g- g+g+ g+g- ag+ T/L NI V Ring Interactions: T/L = T- or L-shaped V = V-shaped NI = No Interaction V T/L V

16.  The B3LYP-DCP method is significantly faster than other methods while still identifying experimentally observed conformers among the lowest energy results  Easily implemented in Gaussian without programming experience  Computational results for FY and YF:  FY: Three lowest energy structures are analogous to experimental results for FF (and WY)  YF: Two lowest energy structures analogous to FF_A and FF_C/WY_A

17. Undergraduate Research Assistants: Purdue North Central College of Science and Department of Biology/Chemistry Rosen Center for Advanced Computing Funding from Louis Stokes Alliance for Minority Participation Student support from PNC Honors Program Melanie Shebel Jasmine Moore

18.  Minimum of 5 starting structures  Revising protocol to use more  Molecule dynamics simulation  Amber, ff14SB force field  150 ns for each starting structure  Select low energy structures  B3LYP-DCP