Benjamin Gung

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Benjamin W. Gung (born July 15, 1953) is a Chinese American organic chemist and academic. He is an emeritus Professor of Chemistry at Miami University. [1]

Contents

Gung and his research group have concentrated on two main areas: organic synthesis, including the total synthesis of natural products and the development of new methodologies, and the study of nonbonding interactions involving aromatic rings. Together, they have synthesized a variety of natural products. [2] [3]

Gung is ranked among the top 2 percent of researchers worldwide, according to a recent Stanford University study that used citation analysis to identify leading scholars among nearly eight million authors. [4]

Education and career

After receiving a bachelor's degree in chemistry from Nanjing University in China in 1982, Gung pursued graduate studies in organic chemistry at Kansas State University, where he completed his M.S. in 1984 and Ph.D. in 1987, studying under Richard McDonald and Duy Hua. Following a two-year postdoctoral appointment at the University of South Carolina under James Marshall, he joined the faculty at Miami University, in Oxford, Ohio in 1989. He was promoted to associate professor in 1994 and Full Professor in 2003, and during his tenure there, he spent his sabbatical leave doing research in the group of William Roush at the University of Michigan in 1999. Since 2024, he has been serving as an emeritus Professor. [5]

Gung has supervised graduate and undergraduate students in chemistry research. [6] [7] [8] He has held key roles, including serving as a reviewer for five NSF-Career Applications in 2004 and organizing an NSF-sponsored REU program at Miami University from 2004 to 2006. [9] He also reviewed NIH Fellowship Study Sections from 2006 to 2011 and was a Co-PI on an NSF-DUE project from 2011 to 2014. [10] After retiring in 2024, he continues collaborating with undergraduate students on research, with his publication, co-authored with Miami University students, focusing on amino acids and peptides as effective ligands for metal-centered catalysts [11]

Research

Gung has made contributions to the field of organic chemistry, with over 100 published journal articles. His research interests include stereochemistry in organic reactions, [12] [13] non-covalent molecular interactions, [14] [15] [16] methods development, [17] and computational chemistry. [18] [19] He is known for his studies in stereochemical mechanism [12] [13] and in the development of a Transannular [4+3] cycloaddition reaction with gold-stabilized allylic carbocations as reactive intermediate. [20] [21]

Selected articles

Related Research Articles

<span class="mw-page-title-main">Aromatic compound</span> Compound containing rings with delocalized pi electrons

Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's Rule. Aromatic compounds have the following general properties:

<span class="mw-page-title-main">Diels–Alder reaction</span> Chemical reaction

In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a pericyclic reaction with a concerted mechanism. More specifically, it is classified as a thermally allowed [4+2] cycloaddition with Woodward–Hoffmann symbol [π4s + π2s]. It was first described by Otto Diels and Kurt Alder in 1928. For the discovery of this reaction, they were awarded the Nobel Prize in Chemistry in 1950. Through the simultaneous construction of two new carbon–carbon bonds, the Diels–Alder reaction provides a reliable way to form six-membered rings with good control over the regio- and stereochemical outcomes. Consequently, it has served as a powerful and widely applied tool for the introduction of chemical complexity in the synthesis of natural products and new materials. The underlying concept has also been applied to π-systems involving heteroatoms, such as carbonyls and imines, which furnish the corresponding heterocycles; this variant is known as the hetero-Diels–Alder reaction. The reaction has also been generalized to other ring sizes, although none of these generalizations have matched the formation of six-membered rings in terms of scope or versatility. Because of the negative values of ΔH° and ΔS° for a typical Diels–Alder reaction, the microscopic reverse of a Diels–Alder reaction becomes favorable at high temperatures, although this is of synthetic importance for only a limited range of Diels–Alder adducts, generally with some special structural features; this reverse reaction is known as the retro-Diels–Alder reaction.

<span class="mw-page-title-main">Charge-transfer complex</span> Association of molecules in which a fraction of electronic charge is transferred between them

In chemistry, charge-transfer (CT) complex, or electron donor-acceptor complex, describes a type of supramolecular assembly of two or more molecules or ions. The assembly consists of two molecules that self-attract through electrostatic forces, i.e., one has at least partial negative charge and the partner has partial positive charge, referred to respectively as the electron acceptor and electron donor. In some cases, the degree of charge transfer is "complete", such that the CT complex can be classified as a salt. In other cases, the charge-transfer association is weak, and the interaction can be disrupted easily by polar solvents.

The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen. Hence, the reaction is sometimes referred to as the Huisgen cycloaddition. 1,3-dipolar cycloaddition is an important route to the regio- and stereoselective synthesis of five-membered heterocycles and their ring-opened acyclic derivatives. The dipolarophile is typically an alkene or alkyne, but can be other pi systems. When the dipolarophile is an alkyne, aromatic rings are generally produced.

In organic chemistry, arynes and benzynes are a class of highly reactive chemical species derived from an aromatic ring by removal of two substituents. Arynes are examples of didehydroarenes, although 1,3- and 1,4-didehydroarenes are also known. Arynes are examples of alkynes under high strain.

An alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applicable to organic synthesis. Being a cycloaddition reaction, it has high atom economy. Many variations have been developed, including cyclisation of mixtures of alkynes and alkenes as well as alkynes and nitriles.

<span class="mw-page-title-main">Nucleophilic aromatic substitution</span> Chemical reaction mechanism

A nucleophilic aromatic substitution (SNAr) is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compounds do undergo nucleophilic substitution. Just as normally nucleophilic alkenes can be made to undergo conjugate substitution if they carry electron-withdrawing substituents, so normally nucleophilic aromatic rings also become electrophilic if they have the right substituents.

<span class="mw-page-title-main">Prelog strain</span> Interactions between atomic groups on different parts of a ring molecule

In organic chemistry, transannular strain is the unfavorable interactions of ring substituents on non-adjacent carbons. These interactions, called transannular interactions, arise from a lack of space in the interior of the ring, which forces substituents into conflict with one another. In medium-sized cycloalkanes, which have between 8 and 11 carbons constituting the ring, transannular strain can be a major source of the overall strain, especially in some conformations, to which there is also contribution from large-angle strain and Pitzer strain. In larger rings, transannular strain drops off until the ring is sufficiently large that it can adopt conformations devoid of any negative interactions.

In organic chemistry, a cyclophane is a hydrocarbon consisting of an aromatic unit and a chain that forms a bridge between two non-adjacent positions of the aromatic ring. More complex derivatives with multiple aromatic units and bridges forming cagelike structures are also known. Cyclophanes are well-studied examples of strained organic compounds.

<span class="mw-page-title-main">Cation–π interaction</span> Noncovalent molecular interaction

Cation–π interaction is a noncovalent molecular interaction between the face of an electron-rich π system (e.g. benzene, ethylene, acetylene) and an adjacent cation (e.g. Li+, Na+). This interaction is an example of noncovalent bonding between a monopole (cation) and a quadrupole (π system). Bonding energies are significant, with solution-phase values falling within the same order of magnitude as hydrogen bonds and salt bridges. Similar to these other non-covalent bonds, cation–π interactions play an important role in nature, particularly in protein structure, molecular recognition and enzyme catalysis. The effect has also been observed and put to use in synthetic systems.

The Wulff–Dötz reaction (also known as the Dötz reaction or the benzannulation reaction of the Fischer carbene complexes) is the chemical reaction of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex with an alkyne and carbon monoxide to give a Cr(CO)3-coordinated substituted phenol. Several reviews have been published. It is named after the German chemist Karl Heinz Dötz (b. 1943) and the American chemist William D. Wulff (b. 1949) at Michigan State University. The reaction was first discovered by Karl Dötz and was extensively developed by his group and W. Wulff's group. They subsequently share the name of the reaction.

<span class="mw-page-title-main">Smiles rearrangement</span> Organic reaction

In organic chemistry, the Smiles rearrangement is an organic reaction and a rearrangement reaction named after British chemist Samuel Smiles. It is an intramolecular, nucleophilic aromatic substitution of the type:

<span class="mw-page-title-main">Annulation</span> Chemical reaction constructing a new ring on a molecule

In organic chemistry, annulation is a chemical reaction in which a new ring is constructed on a molecule.

<span class="mw-page-title-main">Organonickel chemistry</span> Branch of organometallic chemistry

Organonickel chemistry is a branch of organometallic chemistry that deals with organic compounds featuring nickel-carbon bonds. They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. Organonickel compounds are also short-lived intermediates in organic reactions. The first organonickel compound was nickel tetracarbonyl Ni(CO)4, reported in 1890 and quickly applied in the Mond process for nickel purification. Organonickel complexes are prominent in numerous industrial processes including carbonylations, hydrocyanation, and the Shell higher olefin process.

<span class="mw-page-title-main">Staudinger synthesis</span> Form of chemical synthesis

The Staudinger synthesis, also called the Staudinger ketene-imine cycloaddition, is a chemical synthesis in which an imine 1 reacts with a ketene 2 through a non-photochemical 2+2 cycloaddition to produce a β-lactam3. The reaction carries particular importance in the synthesis of β-lactam antibiotics. The Staudinger synthesis should not be confused with the Staudinger reaction, a phosphine or phosphite reaction used to reduce azides to amines.

Melanie Sarah Sanford is an American chemist, currently the Moses Gomberg Distinguished University Professor of Chemistry and Arthur F. Thurnau Professor of Chemistry at the University of Michigan. She is a Fellow for the American Association for the Advancement of Science, and was elected a member of the National Academy of Sciences and the American Academy of Arts and Sciences in 2016. She has served as an executive editor of the Journal of the American Chemical Society since 2021, having been an associate editor of the since 2014.

<span class="mw-page-title-main">Anthony Barrett</span> British chemist

Anthony Gerard Martin Barrett is a British chemist, and Sir Derek Barton Professor of Synthesis, Glaxo Professor of Organic Chemistry at Imperial College London. He is Director of the Wolfson Centre for Organic Chemistry in Medical Science. He was elected a fellow of the Royal Society in 1999 and Academy of Medical Sciences in 2003. He obtained a BSc as well as PhD from Imperial College London in 1973 and 1975 respectively.

Tehshik Peter Yoon is a Canadian-born chemist who studies the new reaction methods for organic synthesis with the use of catalysis. Yoon currently is a professor at the University of Wisconsin–Madison in the chemistry department. For his contributions to science, he has received numerous awards including the Beckman Young Investigator Award and National Science Foundation CAREER Award.

Thomas Lectka is an American organic chemist, academic and researcher. He is Jean and Norman Scowe Professor of Chemistry and leads the Lectka Group at Johns Hopkins University.

<span class="mw-page-title-main">W. Dean Harman</span>

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References

  1. ↑ "Benjamin W. Gung, Ph.D. | Department of Chemistry and Biochemistry | CAS". Miami University.
  2. ↑ "Miami Faculty Recognized Among Top Scholars" (PDF).
  3. ↑ "Benjamin W. Gung". scholar.google.com.
  4. ↑ "More than 20 Miami professors among top 2% of researchers based on analysis of citations". www.miamioh.edu.
  5. ↑ "Emeritus Faculty⎮Department of Chemistry and Biochemistry". Miami University.
  6. ↑ "CAS announces its 2023-24 Dean's Scholars". Miami University. May 5, 2023.
  7. ↑ "Past Members". Sharma Laboratory.
  8. ↑ "Mason Krysinski Chosen Academic All-MAC". Miami University RedHawks. January 31, 2013.
  9. ↑ "NSF Award Search: Award # 0353179 - REU: Summer Undergraduate Research in Chemistry at Miami University, Oxford". www.nsf.gov.
  10. ↑ "NSF Award Search: Award # 1044549 - Collaboration and Guided Inquiry in the Organic Chemistry Laboratory". www.nsf.gov.
  11. ↑ Gung, Benjamin W.; Kubesch, Cole; Bernstein, Gavriella (November 29, 2024). "Natural Chiral Ligand Strategy: Metal-Catalyzed Reactions with Ligands Prepared from Amino Acids and Peptides". Catalysts. 14 (11): 813. doi: 10.3390/catal14110813 .
  12. 1 2 Gung, Benjamin W. (April 8, 1996). "Diastereofacial selection in nucleophilic additions to unsymmetrically substituted trigonal carbons". Tetrahedron. 52 (15): 5263–5301. doi:10.1016/0040-4020(95)01023-8 – via ScienceDirect.
  13. 1 2 Gung, Benjamin W. (May 12, 1999). "Structure Distortions in Heteroatom-Substituted Cyclohexanones, Adamantanones, and Adamantanes: Origin of Diastereofacial Selectivity". Chemical Reviews. 99 (5): 1377–1386. doi:10.1021/cr980365q – via ACS Publications.
  14. ↑ Gung, Benjamin W.; Xue, Xiaowen; Reich, Hans J. (April 29, 2005). "The strength of parallel-displaced arene-arene interactions in chloroform". The Journal of Organic Chemistry. 70 (9): 3641–3644. doi:10.1021/jo050049t. PMID   15845001 – via PubMed.
  15. ↑ Gung, Benjamin W.; Patel, Mehul; Xue, Xiaowen (December 1, 2005). "A Threshold for Charge Transfer in Aromatic Interactions? A Quantitative Study of π-Stacking Interactions". The Journal of Organic Chemistry. 70 (25): 10532–10537. doi:10.1021/jo051808a. PMID   16323868 – via ACS Publications.
  16. ↑ Gung, B. W.; Amicangelo, J. C. (2006). "Substituent Effects in C6F6-C6H5X Stacking Interactions - PMC". The Journal of Organic Chemistry. 71 (25): 9261–9270. doi:10.1021/jo061235h. PMC   2527057 . PMID   17137351.
  17. ↑ Marshall, James A.; Welmaker, Gregory S.; Gung, Benjamin W. (January 1, 1991). "On the 1,3-isomerization of nonracemic .alpha.-(alkoxy)allylstannanes". Journal of the American Chemical Society. 113 (2): 647–656. Bibcode:1991JAChS.113..647M. doi:10.1021/ja00002a038 – via ACS Publications.
  18. ↑ Gung, Benjamin W.; Xue, Xiaowen; Roush, William R. (September 1, 2002). "The Origin of Diastereofacial Control in Allylboration Reactions Using Tartrate Ester Derived Allylboronates: Attractive Interactions between the Lewis Acid Coordinated Aldehyde Carbonyl Group and an Ester Carbonyl Oxygen". Journal of the American Chemical Society. 124 (36): 10692–10697. Bibcode:2002JAChS.12410692G. doi:10.1021/ja026373c. PMID   12207523 – via ACS Publications.
  19. ↑ Gung, B. W.; Xue, X.; Zou, Y. (2007). "Enthalpy (ΔH) and Entropy (ΔS) for π-Stacking Interactions in near-Sandwich Configurations: The Relative Importance of Electrostatic, Dispersive, and Charge-Transfer Effects - PMC". The Journal of Organic Chemistry. 72 (7): 2469–2475. doi:10.1021/jo062526t. PMC   2631381 . PMID   17338571.
  20. ↑ Craft, Derek T.; Gung, Benjamin W. (October 6, 2008). "The first transannular [4+3] cycloaddition reaction: synthesis of the ABCD ring structure of cortistatins". Tetrahedron Letters. 49 (41): 5931–5934. doi:10.1016/j.tetlet.2008.07.155. PMC   2597840 . PMID   19812680.
  21. ↑ Gung, Benjamin W.; Craft, Derek T.; Bailey, Lauren N.; Kirschbaum, Kristin (January 11, 2010). "Gold-catalyzed transannular [4+3] cycloaddition reactions". Chemistry (Weinheim an der Bergstrasse, Germany). 16 (2): 639–644. doi:10.1002/chem.200902185. PMC   3539418 . PMID   19937623.
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