1

CURRICULUM VITA BRUCE ALAN HATHAWAY

Colleges Attended

The University of Texas at Austin, 1972-1976, B. S. in Chemistry (with Honors)

Purdue University, 1976-1980, Ph. D. in Medicinal Chemistry.

Thesis Title: "A New Potent Rigid Analogue of Amphetamine: 2-amino-1,2- dihydronaphthalene (2-ADN).

Chronology of Professional Employment

1980-1982: Post-doctoral Research Associate, Pomona College (with Corwin Hansch)

1982-1988: Assistant Professor of Chemistry, Southeast Missouri State University

1988-1997: Associate Professor of Chemistry, Southeast Missouri State University

1997-Present: Professor of Chemistry, Southeast Missouri State University

List of Publications: (Undergraduate student co-authors are underlined)

31. B. A. Hathaway, U. J. Kilgore and M. R. Bond, “1,2-Diiodo-4,5-dimethylbenzene” Acta Cryst. 2009, E65, 1220.

30. B. A. Hathaway, U. J. Kilgore and M. R. Bond, “1-Ethyl 2,2-dimethyl 3-(1,3- benzodioxol-5-yl)propane-1,2,2-tricarboxylate.” Acta Cryst. 2008, C64, 456–458.

29. B. A. Hathaway, K. L. White and M. E. McGill, “Comparison of Iodination of Methoxylated Benzaldehydes and Related Compounds Using Iodine/Silver Nitrate and Iodine/Periodic Acid,” Synthetic Communications 2007, 37 (21), 3855-3860.

28. D. G. Grohmann and B. A. Hathaway, “3-[(Benzylsulfonyl)methyl]aniline hydrochloride” Molbank 2006, M503. (http://www.mdpi.org/molbank/molbank2006/m503.htm)

27. D. G. Grohmann and B. A. Hathaway, “3-[(Phenylsulfonyl)methyl]aniline hydrochloride” Molbank 2006, M502. (http://www.mdpi.org/molbank/molbank2006/m502.htm)

26. D. G. Grohmann and B. A. Hathaway, “1-Nitro-3-[(benzylsulfonyl)methyl]benzene” Molbank 2006, M501. (http://www.mdpi.org/molbank/molbank2006/m501.htm) 2

25. D. G. Grohmann and B. A. Hathaway, “1-Nitro-3-[(phenylsulfonyl)methyl]benzene” Molbank 2006, M500. (http://www.mdpi.org/molbank/molbank2006/m500.htm)

24. B. A. Hathaway, “Organic Chemistry, The Easy Way”, Barrons Educational Series, Inc., Hauppauge, NY, 2006.

23. B. A. Hathaway and C. L. Chittenden, “Reduction of 2- and 4-Alkylcyclohexanones with Sodium Borohydride in Alcohol Solvents: The Effect of the Solvent on the Stereochemistry of the Product.” Transactions of the Missouri Academy of Science 2001, 35, 13-15.

22. B. A. Hathaway and M. M. Triefenbach , “4-(Benzylsulfonyl)Acetophenone.” Molecules 2001, 6, M245. (http://www.mdpi.org/molbank/m0245.htm)

21. B. A. Hathaway and M. M. Triefenbach, “4-(Benzylthio)Acetophenone.” Molecules 2001, 6, M244.(http://www.mdpi.org/molbank/m0244.htm)

20. B. A. Hathaway and S. W. Blanner, "1-(4-nitrophenyl)-1-octyne" Molecules 2000, 5, M171. (http://www.mdpi.org/molbank/m0171.htm).

19. B. A. Hathaway and R. A. Mueller, "4,5-Dihydro-3-(4-chlorophenyl)-5- decylisoxazole" Molecules 1999, 4, M124. (http://www.mdpi.org/molbank/m0124.htm).

18. B. A. Hathaway, F. G. Peltan, R. A. Mueller, and R. M. Redfearn, "3a, 4, 5, 6, 7, 8, 9, 9a-Octahydro-3-(4-chlorophenyl)cyclooct[d]isoxazole", Molecules 1999, 4, M123. (http://www.mdpi.org/molbank/m0123.htm).

17. B. A. Hathaway and R. A. Mueller, "3a, 4, 5, 6, 7, 8, 8a-Heptahydro-3-(4- chlorophenyl)cyclohept[d]isoxazole" Molecules 1999, 4, M122. (http://www.mdpi.org/molbank/m0122.htm).

16. B. A. Hathaway and R. A. Mueller, "3a, 4, 5, 6, 7, 8, 9, 10, 11, 12,13,13a- Dodecahydro-3-(4-chlorophenyl)cyclododeca[d]isoxazole" Molecules 1999, 4, M121. (http://www.mdpi.org/molbank/m0121.htm).

15. M. Lewis, C. L. Barnes, B. A. Hathaway, and R. Glaser, “4-Methoxybenzaldehyde- (pentafluoromethylidene)hydrazone”, Acta Cryst. 1999, C55, 975 - 978.

14. B. A. Hathaway, G. Day, M. Lewis, and R. Glaser, "Synthesis, Structure, Electrostatic Properties and Spectroscopy of 3-Methyl-4,5,6,7-tetrafluoro-1H-Indazole, J. Chem. Soc, Perkin Trans. 2 1998, 2713-2720.

13. B. A. Hathaway, B. E. Taylor, and J. S. Wittenborn, "Selective Preparation of 4- (Bromo or Iodo)-2,5-Dimethoxybenzonitrile and 2-(Bromo or Iodo)-3,6- Dimethoxybenzonitrile From 2,5-Dimethoxybenzaldehyde", Synthetic Communications 1998, 28(24), 4629-4637. 3

12. B. A. Hathaway, "N-(5-Phenyl-2,4-pentadiynyl)-1,2,3,4-tetrahydro-carbazole", Molecules 1998, 3, M75. (http://www.mdpi.org/molbank/m0075.htm).

11. B. A. Hathaway, "Reduction of 2,6-Dimethylcyclohexanone with Sodium Borohydride Revisited.", J. Chem. Educ. 1998, 75(12), 1623-4.

10. B. A. Hathaway and A. M. Scates, "Preparation and Solution Polymerization of Diacetylenes." J. Chem. Educ., 1997, 74, 111.

9. B. A. Hathaway and B. Olesen, "Determining Hammett Sigma and Rho Values: Improvements on a Published Student Experiment." J. Chem. Educ., 1993, 70, 953-5.

8. B. A. Hathaway, "An Investigation into the Mechanism of the Ritter Reaction." J. Chem. Educ., 1989, 66, 776.

7. B. A. Hathaway, "An Aldol Condensation Experiment Using a Number of Aldehydes and Ketones." J. Chem. Educ., 1987, 64, 367-368.

6. B.A. Hathaway, Z. Guo, C. Hansch, T.J. Delcamp, S.S. Susten, and J.H. Freisheim, "Inhibition of Human Dihydrofolate Reductase by 4,6-Diamino-1,2-dihydro-2,2-dimethyl- 1-(substituted-phenyl)-s-triazines. A Quantitative Structure-Activity Relationship Analysis." J. Med. Chem., 1984, 27, 144-149.

5. C. Hansch, B.A. Hathaway, Z. Guo, C.D. Selassie, S.W. Dietrich, J.M. Blaney, R. Langridge, K.W. Volz, and B.T. Kaufman, "Crystallography, QSAR, and Molecular Graphics in a Comparative Analysis of the Inhibition of Dihydrofolate Reductase fron Chicken Liver and L. casei by 4,6-Diamino-1,2-dihydro-2,2-dimethyl-1-(x-phenyl)- s-triazines." J. Med. Chem., 1984, 27, 129-143.

4. B.A. Hathaway, D.E. Nichols, M.B. Nichols, and G.K.W. Yim, "A New, Potent, Conformationally-Restricted Analogue of Amphetamine: 2-Amino-1,2- dihydronaphthalene." J. Med. Chem., 1982, 25, 535-538.

3. P.J. Kothari, B.A. Hathaway, D.E. Nichols, and G.K.W. Yim, "Synthesis and Seotonin- like Activity of 2-Amino-5,8-dimethoxy-6-methyl-1,2-dihydronaphthalene." J. Med. Chem., 1981, 24, 882-884.

2. G.P. Miggliaccio, T.L.N. Shieh, S.R. Byrn, B.A. Hathaway, and D.E. Nichols, "Comparison of Solution Conformational Preferences for the Hallucinogens Bufotenin and Psilocin Using 360-MHz Proton NMR Spectroscopy." J. Med. Chem., 1981, 24, 206-209.

1. D.E. Nichols, R. Woodard, B.A. Hathaway, M.T. Lowy and G.K.W. Yim, "Resolution and Absolute configuration of trans-2-(2,5-Dimethoxy-4-methylphenyl)cyclopropylamine, a Potent Hallucinogen Analog." J. Med. Chem., 1979, 22, 458-460. 4

Papers Presented at Professional Meetings: (Undergraduate student co-authors are underlined; Presenters are stared)

41. Bruce A. Hathaway, “Oxidation of Benzaldehydes to Benzoate Esters as a Student Discovery Laboratory.” 20th Biennial Conference in Chemical Education, Bloomington, IN, July 27, 2008.

40. Bruce A. Hathaway, “Synthesis and Evaluation of Substituted 1,6-Dihydro-1,3,5- triazine-2,4-diamines as Potential Antimicrobial Compounds.” Invited presentation at Copperbelt University, Kitwe, Zambia, June 9, 2008.

39. Bruce A. Hathaway*, Kristen L. Gilbert and Mark E. McGill, “Comparison of Iodination of Methoxylated Benzaldehydes and Related Compounds Using Iodine/Silver Nitrate and Iodine/Periodic Acid.“ 42nd Midwest Regional Meeting of the American Chemical Society, Kansas City, MO, November 8, 2007.

38. Daniel Grohmann*, Bruce Hathaway, Marcus Cuff, and James Champine, “Synthesis of 4,6-Diamino-1,2-dihydro-2,2-dimethyl-1-[3- or 4-(substituted-thio)phenyl]- s-triazines. Inhibition of the Growth of Lactobacillus rhamnosus ATCC 7469 by the Synthesized Triazines.” Organic Chemistry Day, Columbia MO, April 29, 2006.

37. Mark McGill* and Bruce Hathaway, “Design and Synthesis of a Variety of 3- Alkylanilines: Multiple and Varied Approaches for Intermediates for Potential Antibacterial Compounds.” Organic Chemistry Day, Columbia MO, April 29, 2006.

36. Bruce A. Hathaway*, James E. Champine, Carlos Casteñeda, and Andrea Van Weelden, “Synthesis of 1-(4-Chlorophenyl)-6-alkyl-1,6-dihydro-1,3,5-triazine-2,4- diamines as Potential Antimicrobial Compounds.” 61st Southwest and 57th Southeast Joint Regional Meeting of the American Chemical Society, Memphis, TN, Nov. 3, 2005.

35. Andrea van Weelden*, Carlos Casteneda, Bruce A. Hathaway, and James E. Champine, “Bioassay of Cycloguanil Derivatives for Potential Anti-tumor and Antimicrobial Activities: An Interdisciplinary Project.” Joint ASM Branch Annual Meeting & Midwest Nicrobiology Educators Conference, St. Louis, MO, April 9, 2005.

34. Kristen L. Gilbert* and Bruce A. Hathaway, “Iodination of Mono- and Disubstituted Benzaldehydes.” Organic Chemistry Day, Columbia, MO, April 26, 2003.

33. Kristen L. Gilbert*, Mary M. Triefenbach and Bruce A. Hathaway, “Synthesis of Symmetrical and Asymmetrical Azines.” Organic Chemistry Day, Columbia, MO, April 27, 2002.

32. Bruce A. Hathaway*, Kristen L. Gilbert, and Mary M. Triefenbach, “Preparations Of 5-Substituted-1-indanones And 5-Substituted-1-indanone Azines.”, 36th Midwest Regional Meeting of the American Chemical Society, Lincoln, NE, October 10-13, 2001. 5

31. Mary M. Triefenbach*, Bruce A. Hathaway, Scott D. Kirkley, Charles S. Updike, and Rachel M. Phillips, “Preparations Of 5-Haloindanones And 5-Haloindanone Azines.”, 35th Midwest Regional Meeting of the American Chemical Society, St. Louis, MO, October 25-27, 2000.

30. Jennifer L. Abner*, Bruce A. Hathaway and William A. Gilbert, Efforts To Improve On A Literature Synthesis Of The Solvatochromatic Dye, Betaine-30”, 35th Midwest Regional meeting of the American Chemical Society, St. Louis, MO, October 25-27, 2000.

29. Bruce A. Hathaway, “Fun, Foibles, and Follies In Collaborative Research”, ACS Southern Illinois Local Section Meeting, Cape Girardeau, MO, Feb. 7, 2000.

28. B. A. Hathaway*, F. G. Peltan, R. A. Mueller, and R. M. Redfearn, " Reactions of 4- Chlorobenzonitrile Oxide With Alkenes and Alkynes: Extensions on a Published Student Experiment" American Chemical Society 34rd Annual Midwest Regional Meeting, Quincy, IL, Oct. 31, 1999.

27. Bruce A. Hathaway, “Nitrations of Alkyl- and Halobenzenes: Two Experiments Which Help Students Recognize Size, Shape, and Electronic Effects in Electrophilic Aromatic Substitution Reactions.” Missouri Academy of Science Annual Meeting, Cape Girardeau, MO, April 17, 1999.

26. B. A. Hathaway*, and C. L. Chittenden, " Reduction of 2- and 4-Substituted Cyclohexanones with Sodium Borohydride in Alcohol Solvents: The Discovery of a Solvent Effect." American Chemical Society 33rd Annual Midwest Regional Meeting, Wichita, Kansas, Nov. 5, 1998.

25. Bruce A. Hathaway, Graeme Day, Michael Lewis, and Rainer Glaser, "3-Methyl- 4,5,6,7-tetrafluoro-1H-indazole: Synthesis,Structure, Spectroscopy and ab Initio Computational Study." Article 76, "Electronic Conference on Heterocyclic Chemistry '98", H. S.Rzepa and O. Kappe, (Eds), Imperial College Press, 1998, ISBN 981-02- 3594-1 See also http://www.ch.ic.ac.uk/ectoc/echet98/

24. B. A. Hathaway*, A. M. Scates, and M. S. Paley, "Preparation And Non-Linear Optical Properties Of Diacetylenes." American Chemical Society 32nd Annual Midwest Regional Meeting, Tan-Tar-A, MO, October 30, 1997.

23. B. E. Taylor* and B. A. Hathaway, "Preparation Of Nitrile-Containing Diacetylenes To Be Reacted With Organometallic Complexes." American Chemical Society 32nd Annual Midwest Regional Meeting, Tan-Tar-A, MO, October 30, 1997.

22. J. S. Wittenborn* and B. A. Hathaway, "Preparations Of Substituted-2-Amino-1,2- Dihydronaphthalenes (2-ADN's) As Potential Dopamine And Serotonin Agonists." American Chemical Society 32nd Annual Midwest Regional Meeting, Tan-Tar-A, MO, 6

October 30, 1997.

21. B. A. Hathaway*, "Variations on the Aldol Condensation in the Organic Chemistry Laboratory", 30th American Chemical Society Great Lakes Regional Meeting, Chicago, IL, May 30, 1997.

20. B. A. Hathaway*, "Preparation of Diacetylenes as an Undergraduate Organic Laboratory Experiment." 29th American Chemical Society Great Lakes Regional Meeting, Normal, IL, May 21, 1996.

19. P. W. Zimmerman, Jr.* and B. A. Hathaway, "Preparation Of Diacetylenes For Non- Linear Optical Applications." 29th American Chemical Society Great Lakes Regional Meeting, Normal, IL, May 21, 1996.

18. J. B. Josephsen* and B. A. Hathaway, "Preparations of N-substituted-2-Amino-1,2- Dihydronaphthalenes (2-ADN's) as Potential Stimulants and Analgesics." 29th American Chemical Society Great Lakes Regional Meeting, Normal, IL, May 21, 1996.

17. B.A. Hathaway*, A.M. Scates, M.S. Paley and D.O. Frazier, "Preparation of Diacetylenes for NLO Applications." Sixth Annual JOVE Retreat, Monterey, CA, July 6, 1995.

16. J. B. Josephsen* and B. A. Hathaway, "Preparations of N-substituted-2-Amino-1,2- Dihydronaphthalenes (2-ADN's) as Potential Stimulants and Analgesics." Organic Chemistry Day, University of Missouri-Columbia, April 22, 1995.

15. B. A. Hathaway* and A. M. Scates, "Preparation Of Diacetylenes For Non-Linear Optical Applications." Organic Chemistry Day, University of Missouri-Columbia, April 22, 1995.

14. B.A. Hathaway* and K. Reed, "Dehydration Of 1-Benzylcycloalkanols: A Reinvestigation." American Chemical Society 29th Annual Midwest Regional Meeting, Kansas City, MO, November 3, 1994.

13. B.A. Hathaway, J.R. Mabery, A.M. Scates*, M.S. Paley and D.O. Frazier, "Preparation Of Diacetylenes For Non-Linear Optical Applications." American Chemical Society 29th Annual Midwest Regional Meeting, Kansas City, MO, November 3, 1994.

12. B.A. Hathaway*, J.R. Mabery, J. Carrigan, A.M. Scates, M.S. Paley and D.O. Frazier, "Preparation of Diacetylenes for NLO Applications." Fifth Annual JOVE Retreat, Kennedy Space Center, FL, July 7, 1994.

11. B.A. Hathaway* and K. Reed, "Dehydrations and Ritter Reactions of 1- Benzylcyclohexanol and Cyclohexylphenylcarbinol: Is There a Common Carbocation Intermediate?" Missouri Academy of Science 1993 Annual Meeting, Kansas City, MO, April 24, 1993. 7

10. B.A. Hathaway* and B. Olesen, "Improvements on a Published Student Experiment for Determining Hammett Sigma and Rho Values." 204th American Chemical Society National Meeting, Washington DC, August 23, 1992.

9. B.A. Hathaway, "Paper Chromatograghy for Fun and Profit." Tenth Annual SEMO Science & Technology Symposium, October 14, 1989.

8. B.A. Hathaway, "Using the Ritter Reaction to Illustrate Determination of a Reaction Mechanism." Missouri Academy of Science 1989 Annual Meeting, Joplin, Missouri, April 29, 1989.

7. M. McFadden*, S. Overmann, & B.A. Hathaway, "Effects of 2-aminoindanes on Motor Coordination in Mice." Missouri Academy of Science 1988 Annual Meeting, Kirksville, MO, April 29, 1988.

6. B.A. Hathaway, "The Preparation of 5-alkyl-2-aminoindanes as Potential Analgesics." 8th Annual SEMO Science and Technology Symposium, October 24, 1987.

5. B.A. Hathaway*, S.R. Overmann, A.W. Thurston, and R.P. Tolan, "Preparation of 5- Alkyl-2-aminoindanes as Potential Stimulants and Analgesics." Missouri Academy of Science 1987 Annual Meeting, Columbia, Missouri, April 25, 1987.

4. S.R. Overmann*, B.A. Hathaway, A.W. Thurston, and R.P. Tolan, "Neuropharmacology of 2-Aminoindanes." Missouri Academy of Science 1987 Annual Meeting, Columbia, Missouri, April 25, 1987.

3. B.A. Hathaway* and S.R. Overmann*, "Preparation and Neuropharmacology of 5- substituted-2-aminoindanes." Southeast Missouri Club of Sigma Xi, May 7, 1987.

2. B.A. Hathaway, "The Design of Compounds to Relieve Pain." 7th Annual SEMO Science Symposium, October 25, 1986.

1. B.A. Hathaway, "Drug Design and Drug Development, an Overview." 5th Annual SEMO Science Symposium, April 23, 1983.

Recent Awards

2003: Received Post-Professorial Merit 2003: Greek Week Professor of the Year 2001-2: College of Science and Mathematics Research Award 1999: Outstanding Faculty Service Award

External Grants Received 8

6. Bruce Hathaway, "Preparation of Conformationally-Restricted and Fluorinated Azines as Nonlinear Optical Materials.", American Chemical Society - Petroleum Research Fund, 2-1-2000 to 8-31-2003, $30,000.

5. Bruce Hathaway, "JOVE Augmentation Grant", NASA, 1-30-97 to 5-31-98, $18,500.

4. Bruce Hathaway, Jin Gong, and Mohammed Ali, "Improving Undergraduate Instruction and Research with Multinuclear Fourier-Transform NMR", National Science Foundation, 7-1-96 to 6-30-98, $89,997.

3. David Probst, Bruce Hathaway, Jin Gong, Gary Cwick, and J. O. Snowden, "A NASA/University Joint Venture in Space Research (JOVE), A New Proposal", NASA, Fall 1993-Summer 1996, $115,251.

2. A. Gotch, D. Ritter, and B. Hathaway, "Autodesk Education Grant Proposal for Hyperchem", Autodesk Educational Grant Program, Spring 1993, $3,500.

1. R.C. Briner, B.A. Hathaway, B. Olesen, & R.E. Popham, "Fourier-Transform Infra- Red Spectrometer", Missouri Department of Public Safety, Summer 1988, $67,500.

Internal Grants Received

7. Bruce Hathaway, “Preparation Of Substituted Phenyltriazines as Potential Antimicrobial Drugs”, Southeast Missouri State University Grants and Research Funding Committee, May 2005-Dec. 2006, $3,733.

6. Bruce Hathaway and Bjorn Olesen, “Preparation of Substituted Benzylpyrimidines and Potential Antimicrobial Drugs.”, Southeast Missouri State University Grants and Research Funding Committee, May 2001-Dec. 2002, $3,677.

5. Bruce Hathaway, "Preparation of 2-Amino-1,2-dihydronaphthalenes as Analgesics and Stimulants," Southeast Missouri State University Grants and Research Funding Committee, 7-1-95 to 1-15-98, $2,658.

4. B.A. Hathaway "Preparation and Dehydration of Selected Cyclic Alcohols." Southeast Missouri State University Grants and Research Funding Committee, Spring 1993, $1,576

3. B.A. Hathaway, "Preparation of Potential Analgesics", Southeast Missouri State University Grants and Research Funding Committee, 1989-1991, $1,288.

2. B.A. Hathaway and S.R. Overmann, "Pharmacological Evaluation of 2-Aminoindanes as Potential Analgesics", Southeast Missouri State University Grants and Research Funding Committee, 1986-7, $2,512. 9

1. B.A. Hathaway, "2-Aminoindanes as Potential Analgesics", Southeast Missouri State University Grants and Research Funding Committee, 1985-6, $1,254.