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Nanette M. Wachter-Jurcsak

Professor of Chemistry


Degrees

PHD, 1995, Univ Connecticut; MS, 1990, Old Dominion Univ; BS, 1982, St Lawrence Univ


Bio

Nanette M. Wachter is a professor in the Chemistry Department at Hofstra University. She also directs Hofstra University’s Summer Science Research Program (HUSSRP). Dr. Wachter is an organic chemist and earned a Ph.D. in chemistry from the University of Connecticut in 1995. Her dissertation research involved the design of reactive organolithium species for the synthesis of more complex polycyclic molecules. Since joining the Hofstra faculty, Dr. Wachter has mentored scores of undergraduate students in research projects. For three years she served as a counselor on the Council on Undergraduate Research, a national intercollegiate organization promoting high-quality student-faculty research activities. Dr. Wachter has been actively involved in the American Chemical Society, having served as chair of the Long Island subsection of that organization and as a member of the New York section’s committee on undergraduate research. She has received support from The Camille & Henry Dreyfus Foundation and Merck/AAAS. She also was co-principal investigator on an NSF Major Research Instrument grant.

In 2000 Dr. Wachter began laying the groundwork for HUSSRP, a summer program that places science-oriented high school students with Hofstra faculty mentors. In eight years, the program has produced 16 Intel semifinalists. For the past two summers, HUSSRP has received support from National Grid to promote research in energy sustainability and areas of environmental concern.

As a graduate student, Nanette Wachter used NMR spectroscopy to structurally characterize the compounds she synthesized. Her more recent interest in intramolecular hydrogen bonds arose when she synthesized a surprisingly colorful yet relatively simple molecule in her laboratory at Hofstra. According to Professor Wachter, “Its color was so brash and gaudy, it just screamed for attention.'?

Research Interests

1. Synthesis of Furoxans and Evaluating Their Potential as NO-Releasing Pharmaceuticals

Nitric oxide (NO) is an important intercellular signaling molecule and plays a role in a variety of biological processes. NO is a relatively stable molecular free radical produced in biological systems that is capable of scavenging harmful free radicals in vivo. Nitric oxide has many physiological roles; NO serves as a chemical messenger and is involved in the immune, nervous and cardiovascular systems. NO regulates blood vessel dilation, serves as a neurotransmitter, and is involved in the immune response and the regulation of cell death (apoptosis). Recently, 1,2,5-oxadiazole-2-oxides (furoxans, Figure 1) have been shown to release NO in the presence of thiol cofactors. Furoxan derivatives, therefore, may serve therapeutically as NO-generators in vivo. Our research focuses on the synthesis of symmetrically substituted 3,4-dibenzoyl-1,2,5-oxadiazole-2-oxides and, in collaboration with Dr. Nirode, investigating the ability of these compounds to serve as nitric oxide-releasing pharmaceutical agents.1 A combination of spectroscopic techniques are used to characterize the heterocyclic products.

nitric oxide

Figure 1

2. Solvent Effects on Inter- and Intramolecular Hydrogen Bonding in Conjugated Systems.

Hydrogen bonds play an important role in the conformations of biomolecules and are essential to many biochemical reactions. Proton nuclear magnetic resonance spectroscopy is ideal for investigating hydrogen bonds. When hydrogen bonding occurs, the chemical shift of the proton involved in bonding appears further downfield. Low temperature NMR, in particular, is useful for probing hydrogen bonds in solution because proton exchange is slowed. Hydroxyl protons involved in strong intramolecular hydrogen bonding interactions also exchange slowly.

hydrogen bonds

Figure 2

We have measured the 1H NMR spectra of 2'- and 4'-hydroxyacetophenones, 2'- and 4'-hydroxychalcones, and 4-N,N-dimethylamino-2'- and 4'-hydroxychalcones in a variety of deuterated polar aprotic, weakly polar and nonpolar sovents at varying temperatures.2 Ortho-Hydroxyacetophenone and 2'-hydroxychalcones are capable of intramolecular hydrogen bonding between the ortho-hydroxy group and the carbonyl oxygen. In both nonpolar and polar environments, the signal for the phenolic hydrogen 4-N,N-dimethylamino-2'-hydroxychalcone (DMAHC) appears far downfield (>13 ppm) and shifts further downfield as the temperature is lowered.2a Moderately polar and polar aprotic solvents stabilize intramolecular charge transfer and thus enhance resonance-assisted intramolecular hydrogen bonding (RAHB) in DMAHC. As the vibrational energies of the molecules decrease with decreasing temperature, solvent contraction and the degree of solvent molecule reorganization stabilizes charge polarization in the polar solute and supports resonance-assisted intramolecular hydrogen bonding. On the otherhand, para-hydroxyacetophenone and chalcones are not capable of intramoleuclar hydrogen bonding but can participate in solute-solute and solute-solvent intermolecular interactions. While the chemical shift for the phenolic hydrogen of 4'-hydroxyacetophenone and 4'-hydroxychalones does not appear as far downfield, the magnitudes of the temperature dependent proton chemical shifts are much greater than those observed for the ortho-hydroxy isomers. We are continuing to investigate solvent effects on intermolecular hydrogen bonding in these systems by variable temperature proton NMR.

3. Reactivity of 2-Pyridinylcarboxaldehyde in Claisen-Schmidt Condensation Reactions.

While investigating the properties of 4-substituted and heteroaromatic chalcones, prepared by base-catalyzed condensation of appropriate aromatic carboxaldehydes with acetophenone, we encountered an unanticipated kinetic effect on the reactions involving 2-pyridinecarboxaldehyde and 2-quinolinecarboxaldehyde with acetophenone (Scheme 2).3 When 2-pyridinecarboxaldehyde is treated with two equivalents of either the lithium, sodium, or potassium enolates of acetophenone, the reaction proceeds rapidly at room temperature and high yields (+90%) of 1,5-diphenyl-3-(2-pyridinyl)-1,5-pentanedione are achieved. Similar treatment of 2-quinolinecarboxaldehyde with two equivalents of the sodium enolate of acetophenone results in precipitation of 1,5-diphenyl-3-(2-quinolyl)-1,5-pentanedione from the reaction. Lewis bases have been shown to catalyze aldol reactions by altering the aggregation state, and thereby the reactivity, of the metal enolate.4 Our results suggest that interaction between the pyridinyl aldolate and metal ion is significant for systems containing 2-pyridinyl or 2-quinolyl ring systems.

2-Pyridinylcarboxaldehyd

1 Nirode, W. F.; Luis, J. M.; Wicker, J. F.; Wachter, N. M. Bioorg. Med. Chem Lett., 2006, 16(8), 2299-2301.2 (a) Wachter-Jurcsak, N.; Detmer, C.A. Org. Lett. 1999, 1(5), 795-8. (b) Brack, T. L.; Conti, S.; Radu, C.;Wachter-Jurcsak, N. Tetrahedron Lett. 1999, 40, 3995-3998.3 (a) Wachter-Jurcsak, N.; Redin, K.J. Chem. Educ. 2001, 78, 1264-1265. (b) Wachter-Jurcsak, N.; Radu, C.; Redin, K. Tetrahedron Lett. 1998, 39, 3903-3906. (c) Wachter-Jurcsak, N.; Zamani, H.J. Chem. Educ. 1998, 76, 653-654.4 (a) Hall, P.L.; Harrison, A.T.; Fuller, D.J.; Collum, D.B.J. Am. Chem. Soc. 1991, 113, 9575-85. (b) Willard, P.G.; Hintze, M.J.J. Am. Chem. Soc. 1990, 112, 8602-4. (c) Willard, P.G.; Salvino, J.M. Tetrahedron Lett. 1985, 26, 3931-4.

Hofstra Horizons Articles:

Recent Courses Taught

Course Title Level
CHEM 130 ORGANIC CHEMISTRY PRINCIPLES Undergraduate
CHEM 135 FOUNDATIONS OF ORGANIC CHEM Undergraduate
CHEM 137 FOUNDATNS IN ORGANIC CHEM LAB Undergraduate
CHEM 151 UNDERGRAD RESEARCH 1 Undergraduate
CHEM 152 UNDERGRAD RESEARCH 2 Undergraduate
CHEM 172 ADV ORG CHEM:REACTNS&SYNTHESIS Undergraduate
CHEM 174 ADV ORGANIC SYNTHESIS LAB Undergraduate
CHEM 175 MEDICINAL CHEMISTRY Undergraduate
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