Edyta GreerEdyta Greer, Ph.D.

Associate Professor of Computational Chemistry

Email: Edyta.Greer@baruch.cuny.edu
   Phone: (646) 660-6220

 

Education

Ph.D.: Graduate Center, CUNY

Postdoctoral Research: Cornell University

Current Research Interests:

Research in my group focuses on theoretical and experimental approaches to novel enediyne drugs that undergo the Bergman cyclization to kill cancerous cells.  For example, we conduct quantum mechanical calculations to analyze replacement of a carbon fragment with a metal fragment in organic molecules (by means of the isolobal analogy) to “perturb” the energetic of the Bergman cyclization. Such perturbation methods may have interesting implications for Cope and Diels-Alder reactions too.  We also study tropolone molecules, such as the material found in Thuja trees, which exhibit wide but “untamed” cytotoxic properties.  Our synthetic chemistry is targeting the generation of new tropolone compounds with better selective inhibition of the metalloenzyme, HIV-1 integrase.  My group also has two active collaborations; one involving synthetic and mechanistic studies of 1-benzazepine compounds with Prof. Ramig, and the other analyzing natural materials from marine organisms isolated by Prof. Gruber.

Grants

The Petroleum Research Fund of the American Chemical Society Grant No. 54244-UR4 (2014-2018)

 ACS-PRF logo

 

 

Publications:

2008-Present

(*Baruch undergraduate student)

Edyta M. Greer, Kitae Kwon* “Density Functional Theory and ab Initio Computational Evidence for Nitrosamine Photoperoxides: Hammett Substituent Effects in the Photogeneration of the Nitrooxide Intermediate” Photochemistry and Photobiology, 2018, DOI: 10.1111/php.12941

Edyta M. Greer, Kitae Kwon* “Overview of Computational Methods for Organic Chemists” Chapter 2 in Applied Theoretical Organic Chemistry, 2018, 31-65 (Tantillo, D. J., Ed.).

Niluksha Walalawela, Mariana Vignoni, Maria N. Urrutia, Sarah J. Belh, Edyta M. Greer, Andres H. Thomas, Alexander Greer “Kinetic Control in the Regioselective Alkylation of Pterin Sensitizers: A Synthetic, Photochemical, and Theoretical Study” Photochemistry and Photobiology, 2018, DOI: 10.1111/php.12905

Charles Doubleday, Randy Armas, Dana Walker, Christopher V. Cosgriff*, Edyta M. Greer “Heavy-Atom Tunneling Calculations in Thirteen Organic Reactions: Tunneling Contributions are Substantial, and Bell's Formula Closely Approximates Multidimensional Tunneling at ≥250 K” Angewandte Chemie International Edition in English, 2017, 56, 13099-13102. Highlighted by: (1) Gabriella Graziano Nature Reviews-Chemistry2017, 1, Article number: 0086, https://www.nature.com/articles/s41570-017-0086 and (2) Steven Bacharach Computational Chemistry Highlights http://www.compchemhighlights.org/2017/12/heavy-atom-tunneling-calculations-in.html

Ashwini A. Ghogare, Ciro J. Debaz, Marilene Silva Oliveira, Inna Abramova, Prabhu P. Mohapatra, Kitae Kwon,* Edyta M. Greer, Fernanda Manso Prado, Hellen P. Valério, Paolo Di Mascio, Alexander Greer “Experimental and DFT Computational Insight into Nitrosamine Photochemistry - Oxygen Matters” Journal of Physical Chemistry A, 2017, 121, 5954-5966.

Sasan Karimi, Shuai Ma, Yanan Liu, Keith Ramig, Edyta M. Greer, Kitae Kwon,* William F. Berkowitz, Gopal Subramaniam “Substituted Pyrrole Synthesis from Nitrodienes” Tetrahedron Letters201758, 2223-2227.

Edyta M. Greer, Kitae Kwon,* Alexander Greer, Charles Doubleday “Thermally Activated Tunneling in Organic Reactions” Tetrahedron, 2016, 72, 7357-7373.

Keith Ramig,  Gopal Subramaniam, Sasan Karimi, David J. Szalda, Allen Ko,* Aaron Lam,* Jeffrey Li,* Ani Coaderaj,* Leyla Cavdar,* Lukasz Bogdan,* Kitae Kwon,* Edyta M. Greer “Interplay of Nitrogen-​Atom Inversion and Conformational Inversion in Enantiomerization of 1H-​1-​Benzazepines” Journal of the Organic Chemistry, 2016, 81, 3313-3320.

Sasan Karimi, Shuai Ma, Keith Ramig, Edyta M. Greer, David J. Szalda, Gopal Subramaniam “Oxidative Ring-​contraction of 3H-​1-​Benzazepines to Quinoline Derivatives” Tetrahedron Letters201556, 6886-6889.

Marilene Silva Oliveira, Ashwini A. Ghogare, Inna Abramova, Edyta M. Greer, Fernanda Manso Prado, Paolo Di Mascio, Alexander Greer “Mechanism of Photochemical O-​Atom Exchange in Nitrosamines with Molecular Oxygen” Journal of the Organic Chemistry, 2015, 80, 6119-6127.

Edyta M. Greer, Cesar S. Quezada,* Christopher V. Cosgriff* “Butylated Hydroxytoluene Enediyne: Access to Diradical and Electrophilic Quinone Methide Intermediates” Journal of Physical Organic Chemistry, 2015, 28, 365-369.

Allen Ko,* Aaron Lam,* Jeffrey Li,* Edyta M. Greer, David J. Szalda, Sasan Karimi, Gopal Subramaniam, Keith Ramig “Regioselective Alkylation Reactions of 2,​4-​Diphenyl-​3H-​1-​benzazepine Give Either 3-​alkyl-​3H-​1-​benzazepines or 1-​alkyl-​1H-​1-​benzazepines” Tetrahedron Letters, 201455, 4386-4389.

Edyta M. Greer, Christopher V. Cosgriff,* Charles Doubleday “Computational Evidence for Heavy-Atom Tunneling in the Bergman Cyclization of a 10-Membered-Ring Enediyne”  Journal of the American Chemical Society, 2013, 135, 10194-10197. (highlighted on the website of JACS and by Steven Bacharach in Computational Chemistry Highlights (http://www.compchemhighlights.org/2013/07/tunneling-in-bergman-cyclization.html))

Edyta M. Greer, Christopher V. Cosgriff* “Reaction Mechanisms: Pericyclic Reactions” Annual Reports Section “B” (Organic Chemistry), 2013, 109, 328-350.

Keith Ramig, Edyta M. Greer, David J. Szalda, Sasan Karimi, Allen Ko,* Laura Boulos,* Jiansan Gu,* Nathan Dvorkin,* Hema Bhramdat, Gopal Subramaniam, “NMR Spectroscopic and Computational Study of Conformational Isomerism in Substituted 2-Aryl-3H-1-benzazepines: Toward Isolable Atropisomeric Benzazepine Enantiomers” Journal of the Organic Chemistry, 2013, 78, 8028-8036.

 Sasan Karimi, Keith Ramig, Edyta M. Greer, David J. Szalda, William F. Berkowitz, Prakash Prasad, Gopal Subramaniam, “Tandem Ring-Contraction/Decarbonylation of 2,4-Diphenyl-3H-1-benzazepine to 2,4-Diphenylquinoline” Tetrahedron 2013, 69, 147-151.

Edyta M. Greer, Christopher V. Cosgriff,* Olga Lavinda* “A Curtin-Hammett Pentamethylene Chain Symmetrization Process in the Bergman Cyclization of an 11-Membered-Ring Enediyne” Journal of Physical Organic Chemistry, 2012, 25, 1293–1298.

Edyta M. Greer, Christopher V. Cosgriff* “Reaction Mechanisms: Pericyclic Reactions” Annual Reports Section “B” (Organic Chemistry), 2012, 108, 251-271.

Edyta M. Greer, Mariya Tolmachova “Marie Curie: Pioneering Discoveries and Humanitarianism” Helvetica Chimica Acta, 2011, 94, 1893-1907. (featured in CUNY Research Newsletter 2012, 7, 8)

Edyta M. Greer, Olga Lavinda* “Theoretical Study of the Bergman cyclization of 2,3-Diethynyl-1-nitrotropylium Ion: Formation of a Nitroxide Radical Amenable to EPR Detection for Biological Applications” Journal of Organic Chemistry, 2010, 75, 8650-8653.

Keith Ramig, Edyta M. Greer, David J. Szalda, Rabail Razi,* Fahima Mahir,* Nataliya Pokeza,* Wei Wong,* Benjamin Kaplan,* Joanne Lam,* Ayesha Mannan,* Christopher Missak,* Dat Mai,* Gopal Subramaniam, William F. Berkowitz, Prakash Prasad, Sasan Karimi, Ngai Hin Lo, and Linas V. Kudzma “Experimental and Theoretical Studies of a One-flask Synthesis of 3H-1-Benzazepines from 2-Haloanilines and alpha,beta-Unsaturated Ketones” The European Journal of Organic Chemistry, 2010, 2363-2371.

Edyta M. Greer, Roald Hoffmann “Metalla-Cope Rearrangements: Bridging Organic and Inorganic Chemistry” Journal of Physical Chemistry A, 2010, 26, 2248-2255. (highlighted on the front page of the website of the American Chemical Society, and it was the second most accessed paper in the first three months of 2010 for the JPChem A)

Edyta M. Greer, David J. Aebisher, Alexander Greer, Ronald Bentley “Computational Studies of the Tropone Natural Products, Thiotropocin, Tropodithietic Acis, and Troposulfenin.  Significance of Keto-Thiol Tautomerism” Journal of Organic Chemistry, 2008, 73, 280-283.

2003-2007

Edyta M. Brzostowska, Roald Hoffmann, Carol A. Parish “Tuning the Bergman Cyclization by Introduction of Metal Fragments at Various Positions of the Enediyne.  MetallaBergman Cyclizations” Journal of the American Chemical Society, 2007, 129, 4401-4409.

Aaron T. Frank, Nicola S. Farina, Nahed Sawwan, Mo Qi, Edyta M. Brzostowska, Frank W. Grasso, Paul Haberfield, Alexander Greer “Natural Macromolecules Have a Limited Structural Diversity?” Molecular Diversity 2007, 11, 115-118.

David J. Aebisher, Edyta M. Brzostowska, Nahed Sawwan, Rafeal Ovalle, Alexander Greer “Implication for the Existence of a Heptasulfur Linkage in Natural o-Benzopolysulfanes” Journal of Natural Products, 2007, 70, 1492-1494.

Edyta M. Brzostowska, Martine Paulynice, Ronald Bentley, Alexander Greer “Planar Chirality Due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins.  Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity” Chemical Research in Toxicology, 2007, 20, 1046-1052.

David J. Aebisher, Edyta M. Brzostowska, Mahendran Adaickpillai, Alexander Greer “Regioselective (Biomimetic) Synthesis of a Pentasulfane from ortho-Benzoquinone” Journal of Organic Chemistry, 2007, 72, 2951-2955.

Nahed Sawwan, Edyta M. Brzostowska, Alexander Greer “Substituent Effects on the Reactivity of Benzo-1,2-dithiolan-3-one 1-Oxides and Their Possible Application to the Synthesis of DNA-Targeting Drugs” Journal of Organic Chemistry, 2005, 70, 6968-6971.

Edyta M. Brzostowska, Alexander Greer “Polysulfane Antitumor Agents from o-Benzyne. An Odd-Even Alternation Found in the Stability of Products o-C6H4Sx (x=1-8)” Journal of Organic Chemistry, 2004, 69, 5483-5485.

Edyta M. Brzostowska, Alexander Greer “The Role of Amine in the Mechanism of Pentathiepin (Polysulfur) Antitumor Agents” Journal of the American Chemical Society, 2003, 125, 396-404.

(name appears as Edyta M. Brzostowska before 2008)

The Greer Research Group

Current Group Members (Quants):

Carolyn McGrail (undergraduate students) (May 2018 – present)

Frankie Banevides (research assistant, Jan. 2017 – present)

Christopher V. Cosgriff (research assistant, May 2013 – present)

Former Group Members:

17.         Frankie Banevides (Jan. 2017 – Aug. 2018)

16.         Thuong Tran (Jan. 2017 – Aug. 2018)

15.         Kitae (Mikey) Kwon (Aug. 2014 – June 2017)

14.         Anastasia Badziai (Sept. 2015 – Dec. 2015)

13.         Elena Votto (Feb. 2015 – Aug. 2015)

12.         Jade Marino Creto (Aug. 2014 – June 2015)

11.         Lukasz Bogdan (Sept. 2013 – June 2014)

10.         John Ortiz (Sept. 2013 – present)

9.           Cesar Quezada (Sept. 2012 – May 2013)

8.           Michael Erdos (Sept. 2012 – Dec. 2012)

7.           Irina Kushenazarova (Jan. 2011 – May 2012)

6.           Christopher V. Cosgriff (Jan. 2011 – May 2013)

5.           Nathan Dvorkin (Sept. 2010 – Aug. 2012)

4.           Janna Petrovich (Jan. 2010 – May 2011)

3.           Dat Mai (Jan. 2009 – Dec. 2010)

2.           Rose Connor (Sept. 2008 – Dec. 2008)

1.           Olga Lavinda (Sept. 2008 – Jan. 2011)

 

 

The City University of New York