Assistant Professor II
Chemistry, Biochemistry, & Physics
2083 Lawrenceville Road, Lawrenceville, NJ 08648
Education & Experience
2008 Ph.D., University of North Carolina at Chapel Hill (Michael T. Crimmins)
2008 AAAS Mass Media Science & Engineering Fellow
2007 Department of Education GAANN Teaching Fellow
2002 B.S., Haverford College (Frances R. Blase)
Areas of Focus
Organic Chemistry, Physical Organic Chemistry, Science Communication
Current programs in my laboratory focus on the development and application of novel synthetic methodology towards the preparation of natural products and other drug candidates of medical importance.
- Aza-Conjugate Addition of Sulfonamides to 2-Vinyl Pyridine
Sulfonamides and pyridine rings are structural moieties that are embedded into the backbones of an astonishing number of pharmaceuticals on the market today. The promise to easily bring these two functional groups together to create a sulfonamido-pyridyl backbone would thus be of incredible importance to the medical community. However, surprisingly little research exists that examines the bifunctional N-(2-(pyridin-2-yl)ethyl)sulfonamide scaffold for any potential applications. Our laboratory is currently developing a novel and efficient, solvent-free conjugate addition reaction of sulfonamides to 2-vinylpyridine derivatives, providing unique N-(2-(pyridin-2-yl)ethyl)sulfonamide products. Upon optimization of reaction conditions, this protocol will further be applied towards the construction of novel molecular scaffolds for further chemical and pharmaceutical assessment.
- Asymmetric Synthesis of Butenolide-Containing Natural Products
Butenolide-containing natural products and their synthetic derivatives have been long praised in the medical community as important drug candidates for their anti-tumor, anti-inflammation, anti-microbial, and anti-viral activities. It is thus imperative to develop a concise and efficient route to construct these potential pharmaceuticals.
We are currently investigating the novel asymmetric alkylation of chiral glycolyloxazolidinones with α-halomethylacrylates, to facilitate access to libraries of differentially substituted butenolides. Although asymmetric glycolate alkylation employing simple alkyl halides has been exhaustively demonstrated as an efficient method for forming medium-size ring ethers, there are no reports using a non-traditional α,b-unsaturated esters as alkylating agents, which could lead directly to 5-membered lactones with either external or internal olefins.
Upon demonstration of an effective methodology, further elaboration onto these moieties should lead to complex natural products and their novel derivatives that will eventually be evaluated for their biological activity against human disease and infection.
I am also dedicated towards improving science communication and literacy. I am currently involved in an ongoing research project with Rider University librarians where we are creating relevant, easy-to follow online tutorials for SciFinder.
Peer-Reviewed Publications (Students in Bold)
- Ghattas, P.; Carlin, J.W.; Murkli Jr., S.L.; Jacobs, D.L. “Solvent-Free Microwave-Assisted Preparation of N-(2-(Pyridin-2-yl)-ethylsulfonamides.” Synthetic Communications 44 (2014): 1-10.
- Jacobs, D.L.; Chan, B.C.; O’Connor, A.R. “N-[2-(Pyridin-2-yl)ethyl]-Derivatives of Methane-, Benzene- and Toluenesulfonamide: Prospective Ligands for Metal Coordination.” Acta Crystallographica C69 (2013): 1397-1401.
- Dawson, P.H.; Jacobs, D.L.; Yang, S.Q. “An Online Tutorial for SciFinder for Organic Chemistry Classes.” Science & Technology Libraries 29 (2010): 298-306.
- Crimmins, Michael T., & Jacobs, Danielle L. “Asymmetric Total Synthesis of Pyranicin.” Organic Letters 11 (2009): 2695-2698.
Scholarly Presentations (Students in Bold)
- Dawson, P.H.; Yang, S.Q.; Heath, W.P.; Jacobs, D.L. “Creating Online Tutorials: A Way to Embed Research Instruction into Distance Learning and Traditional Classes.” European Conference on Information Literacy. Istanbul, Turkey 22 October 2013.
- Dalal, H.; Dawson, P.H.; Jacobs, D.L.; Yang, S.Q. “Representing Reference: Making the Most Out of Your Subscription Databases: A SciFinder Example.” [Webinar] In Lyrasis Webinar Series. 25 April 2013.
- Murkli Jr., S.L.; Carlin, J.W.; Jacobs, D.L. “Adjuvant-Free Conjugate Addition of Sulfonamides to 2-Vinylpyridines: An Unexploited Facile Route to Diversely Substituted N-(2-(Pyridin-2-yl)-ethyl)sulfonamide Derivatives.” 245th ACS National Meeting, New Orleans 8 April 2013.
- Bing, J. & Jacobs, D.L. “Development of a Novel Asymmetric Alkylation of Superquat-Derived Glycolyloxazolidinones and their Application toward the Synthesis of Majorenolide and Majorynolide.” 244th ACS National Meeting, Philadelphia 20 August 2012.
- Jacobs, D.L.; Blase, F.; Hunt, D.; Minbiole, K. “New Challenges for Organic Synthesis in the Undergraduate Research Lab.” CUR National Meeting, The College of New Jersey 25 June 2012.
- Ghattas, P. & Jacobs, D.L. “Synthesis and reactivity of differentially substituted 2-vinylpyridines in the conjugate addition of benzenesulfonamide.” 243rd ACS National Meeting, San Diego 26 March 2012.
- Wilner, A.; Mirchandani, S.; Lowrey, P.; Spiegelberg, B.; Jacobs, D. “SoTL and the Creative Power of Faculty Learning Communities.” SoTL Commons, Georgia Southern University 7 March 2012.
- Jacobs, D.L.; Dawson, P.H.; Yang, S.Q. “Development and Assessment of Online SciFinder Tutorials Toward the Promotion of Scientific Literacy in Undergraduates.” 242nd ACS National Meeting, Denver 31 August 2011.
- Musumeci, L.E. & Jacobs, D.L.; “Glycolate Alkylations with 2-(Methyliodo)acrylates Toward the Synthesis of Majorynolide & Majorenolide.” 42nd Middle Atlantic Regional Meeting of the ACS, College Park, MD 21 May 2011.
- Ghattas, P. & Jacobs, D.L. “Catalytic, Solvent-Free Preparation of N-(2-(Pyridin-2-yl)-ethyl)sulfonamides.” 42nd Middle Atlantic Regional Meeting of the ACS, College Park, MD 21 May 2011.
- Dawson, P.H.; Jacobs, D.L.; Yang, S.Q. Online Tutorials & Assessment of Information Literacy Skills. Association of Research Libraries (ARL) 2010 Library Assessment Conference, Baltimore, MD 25 October 2010.
- Benning, Jr., Ronald & Jacobs, Danielle. “Investigations into the Aza-Conjugate Addition of Sulfonamides to 2-Vinyl Pyridine.” 240th ACS National Meeting, Boston 23 August 2010.
- Elbaum, Michael B. & Jacobs, Danielle L. “Design, Synthesis, and Evaluation of Novel Cyanoacrylamide Polymers as Drug-Releasing Bioadhesives.” 240th ACS National Meeting, Boston 23 August 2010.
- Dawson, P.H.; Jacobs, D.L.; Yang, S.Q. Online Tutorial for SciFinder for Organic Chemistry Classes: Creation & Assessment of Use. Special Libraries Association (SLA) Annual Conference, New Orleans 15 June 2010.
- Dawson, P.H.; Jacobs, D.L.; Yang, S.Q. Online Tutorial for SciFinder for Organic Chemistry Classes: Creation & Assessment of Use. Virtual Academic Library Environment (VALE) New Jersey Assessment Fair, Piscataway, NJ 25 May 2010.
- Jacobs, Danielle & Crimmins, M.T. “Asymmetric Total Synthesis of Pyranicin.” 238th ACS National Meeting, Washington, D.C. 21 August 2009.
Project SEED Presentations (Students in Bold)
- Sabharwal, S.; Kparway, J.; Jacobs, D.L. “Experiment Comparing Hydrolysis Rates of Varying Aspirin Formulations.” 244th ACS National Meeting, Philadelphia 20 August 2012.
- Furqan, D.; Musumeci, L.; Jacobs, D.L. “Na(SG)-I as a Novel Deprotecting Reagent.” 240th ACS National Meeting, Boston 23 August 2010.
- Leon, L.; Benning, R.T.; Ghattas, P.; Jacobs, D.L. Synthesis of Chiral Auxiliaries from (R)-(+)-Pulegone. 238th ACS National Meeting, Washington, DC. 19 August 2009.