Anthony "Bo" Arduengo was born in 1952 in
Tampa, Florida.[1] He grew up in the
Atlanta,
Georgia area. His father was a pressman and mechanic with the Atlanta Journal-Constitution and instilled his son with an interest and skill for all things mechanical and scientific. By the age of 16, he and his father had built his first car from miscellaneous parts.[2] The car was registered as street-legal and road-worthy. With some re-engineering, the car was later fitted to run on alternate fuels including alcohol and hydrogen (which would foretell Arduengo's professional research involvement with
President Bush's 2003 National Hydrogen Fuel Initiative (HFI)[3] and
United States Department of Energy's Chemical
Hydrogen Storage Program by more than 30 years).
Education
Arduengo attended Bouldercrest and Meadowview Elementary Schools, and
Walker High School.[4] In 1969 he left high school with enrollment in Georgia Tech's Joint Enrollment Program for High School Students (JEPHS).[5] He obtained his
BSc (1974,
cum laude) and his
PhD (1976) at
Georgia Tech, advised by
Edward M. Burgess.[6] That made him an
academic descendant of
Justus von Liebig.[4] As an undergraduate at
Georgia Tech, Arduengo's research activities began in the laboratory of Professor Charles L. Liotta. He was awarded
NSF undergraduate fellowships in 1972 & 1973 when he had moved to research in the
Burgess group.[4]
As an undergraduate, Arduengo was a member of the
Georgia Tech Band and served as Executive Officer and Captain for that organization. In 1971 he was inducted into the Iota chapter[7] of
ΚΚΨ. In 1972 he was tapped by the Alpha Eta Circle[8] of
ΟΔΚ; later serving as Secretary and President for the local Circle.
In
DuPont's Central Research and Development Department, Arduengo began his career in the Chemical Sciences Section (1977 & on return in 1984). In 1988, he was appointed Research Leader. A move into the Polymer Science section of
CR&D in 1991 was accompanied by promotion to Group Leader. His final position with
DuPont was as Research Fellow which he attained in 1995. The award of an
Alexander von Humboldt Senior Research Prize in 1996 began Arduengo's transition back into academe. The one year Humboldt award was spent in
Braunschweig,
Germany at the
Technical University. On return to
DuPont, Arduengo maintained a guest Professor appointment in
Braunschweig, and in 1999 also made the transition to academe in the U.S. with his assumption of the Saxon Chair in Chemistry at The
University of Alabama in
Tuscaloosa.[4][9]
Research
Graduate research at Georgia Tech
Arduengo's research interests focus largely on the chemistry of new or unusual bonding arrangements, and unusual
valency. As a graduate student in the
Burgess group, his research involved organo-
main group element chemistry, specifically, thiocarbonyl
ylides, and low-coordinate
hypervalentsulfur compounds.[6][10][11][12]
Thiocarbonyl ylide from Arduengo's Ph.D. dissertation.
external viewer.
Hypervalent sulfuranide from Arduengo's Ph.D. dissertation.
external viewer.
At
Illinois Arduengo examined more broadly the areas of organo-
main group element chemistry, and molecules containing unusual
valency. His first publications involving the chemistry of
electron-deficientcarbenes occurred during this period.[13] This work with electron deficient carbenes led to the first structure determinations on a
nitrile ylide[14] and a carbonyl
ylide.[15] His later work with
carbene chemistry would become his most recognized contribution to the field of chemistry (vide infra). During the Illinois years Arduengo had a close collaboration with his colleague
J.C. Martin who was a physical-organic chemist also working on organo-
main group element chemistry and hypervalency. Many of the technical discussions between Martin and Arduengo would take place over lunch (the choice of restaurants often influenced by the quality of the napkins for writing chemical structures).[16] To facilitate discussions about unusual molecular structures and bonding for
main-group element centers, Martin and Arduengo devised the
N-X-L nomenclature system.[17][18][19] The synthesis and characterization of the first compound with a planar T-shaped, 10-
electron 3-
coordinate bonding arrangement at a
phosphorus atom, ADPO,[20] was also accomplished by the Arduengo group at Illinois and paved the way for a range of novel
main-group element chemistry (including the discovery of
edge inversion) on his return to
DuPont. The final Illinois research extended the newly discovered ADPO chemistry to the arsenic analog (ADAsO).[21]
Diazotetrakis(trifluoro methyl)cyclopentadiene from Arduengo and Janulis.
external viewer.
On returning to
DuPont in 1984, Arduengo resumed a position in
CR&D and continued the research into the recently discovered ADPO molecule and related structures. This line of research proved to be extremely fruitful and resulted in a steady string of publications on new and unusual bonding arrangements.[22][23] The ADPO related chemistry provided a basis for the discovery of a new inversion process,
edge inversion, which was fully characterized and modelled by the collaborative work of Arduengo and David A. Dixon at
DuPont.[24] Additionally, the
DuPont team provided experimental verification on the new inversion pathway at 3-coordinate
phosphorus centers[25] and a 4-coordinate germanium molecule.[26]
Arduengo's work with
DuPont also involved a number of applied projects including the flexible
polyimide film,
Kapton-ZT, that is widely used in electronics for flexible printed circuits, connections, and insulation.[27] Arduengo's research at
DuPont often coalesced with his other hobbies outside the laboratory; for example with sports cars (cf. photo in the summary box above). He contributed to development of low
VOC automotive coatings by devising
catalysts for a novel
cross-linking chemistry used by
DuPont Performance Coatings in next-generation low-
VOC paints.[28][29][30] Eventually,
DuPont waterborne performance coatings would be used by
Lotus on their
Elise and
Exige models.[31][32] Arduengo's effort on the industrial-scale syntheses[33][34][35] of the
catalysts for the paints on which he worked would launch his re-entry into the area of
carbene chemistry, but this time it was to be
nucleophilic rather than
electrophiliccarbenes.[1][36] The observation that the catalyst syntheses were well tolerant of varied reaction conditions and substituents led Arduengo to postulate that the
imidazol-2-ylidenes that were
intermediates in the syntheses had to be far more stable than the then conventional wisdom would allow.[36][37]
As Arduengo's involvement in the automotive coatings program came to an end, he submitted a proposal to the management in
CR&D to isolate these apparently
stable carbenes and study their chemistry. The proposal was soundly declined with the admonition that he should have certainly known better than to make such a suggestion in light of the long history of
carbene chemistry that firmly established them as
reactive intermediates that could not be isolated as stable entities.[1][36][37] However, Arduengo (already well-aware of the history) had the starting materials on hand for the chemistry and decided to proceed with the experiments.[37] "Arduengo's gamble paid off. In 1991, more than 150 years after the first attempt ..."[38] a stable crystalline carbene was isolated and characterized in laboratories at
DuPont.[39] After the first successful reaction to produce a
stable carbene, Arduengo won the support of
DuPont management[37] and research in this area continued.
Carbenes bearing a variety of substituent groups were prepared and characterized.[40][41] The saturated
imidazolin-2-ylidenes that were extensively investigated by
Hans-Werner Wanzlick thirty years earlier (without isolation) were now also shown to be stable enough to isolate with appropriate substituents at nitrogen.[42] An air-stable carbene was produced.[43] The chemistry was extended to include thiazol-2-ylidenes (conjectured to exist in 1957 as a
reactive intermediate in the
vitamin B1catalytic cycle, but not isolated for 40 years).[44] The imidazol-2-ylidenes were extensively characterized by their
NMR properties,[45]photo-electron spectroscopy,[46] and exact experimental electron density mapping by
X-ray and
neutron diffraction techniques.[47]
In 1998, Arduengo and coworkers carefully re-examined the earlier attempts to produce stable carbenes in Wanzlick's laboratory in light of the knowledge and experience gained from the recent successful experiments at DuPont.[66] Although the majority of Wanzlick's work on the saturated
imidazolin-2-ylidenes would have been expected to yield dimers in the absence of bulky substituents on nitrogen, a single (unsaturated)
imidazol-2-ylidene, 1,3,4,5-tetraphenylimidazol-2-ylidene, remained as an example of a carbene that could (should) have been isolable. The re-examination of Wanzlick's original procedure[67] identified some key experimental features that would have hindered the original researchers. With these problems corrected, the DuPont scientists were able to isolate the target carbene and fully characterize it including an X-ray structure determination. In a tribute to Hans-Werner Wanzlick, these results were published under the title "1,3,4,5-Tetraphenylimidazol-2-ylidene: The Realization of Wanzlick's Dream."[66]
Antimony analog of ADPO (ADSbO) synthesized at DuPont by Arduengo and Stewart.[68]external viewer.
Nine coordinate bismuth complex prepared by Arduengo and Stewart.[69]external viewer.
Saturated ADPO analog used by Arduengo, Dixon, and Roe to verify Edge Inversion at 3-coordinate phosphorus.[25]
Germanium compound used by Arduengo, Dixon, and Roe to verify Edge Inversion at 4-coordinate centers.[26]external viewer.
At the University of Alabama research from Arduengo's laboratory has focused on enhancements to the basic structure of the imidazol-2-ylidenes through substituent effects leading to novel compounds like a
cyclopentadienyl fused imidazol-2-ylidene.[70][71][72][73] Research into the unusual valency in diphosphacyclobutane-2,4-diyls has been reported from the Arduengo group in collaboration with Professors Masaaki Yoshifuji and Shigekazu Ito.[74][75][76][77][78][79][80] Arduengo also directs research programs into Chemical Hydrogen Storage and
nonlinear optical materials.[4] In 2015, together with Professor Till Opatz (Johannes Gutenberg Universität-Mainz) Arduengo founded the StanCE coalition for sustainable chemistry based on woody biomass (
Xylochemistry).[9]
Georgia Tech 2020–present
In June 2020 Arduengo returned to his alma mater as Professor of the Practice.[4][9][81] His research in carbene chemistry continues there along efforts in support of the Medicines for All Institute[82] sustainable chemistry, and a partnership to address repatriation of critical chemical manufacturing technology to U.S. shores.[83][9]
Awards
Charles M. Knight Lectureship, University of Akron, April 2013.[84]
^JEPHSArchived September 5, 2010, at the
Wayback Machine - Georgia Tech's Joint Enrollment Program. Retrieved 2010-10-04.
^
ab
Anthony Joseph Arduengo (1976), The synthesis, structure and chemistry of substituent-perturbed
thione S-methylides and
S,S-dihalothiones Ph.D. Thesis, Georgia Institute of Technology.
Online catalog entry. Retrieved 2009-12-04.
^Iota Chapter Georgia Tech's Iota Chapter of ΚΚΨ. Retrieved 2017-10-07.
^Alpha Eta Circle - Georgia Tech's Alpha Eta Circle of ΟΔΚ. Retrieved 2013-02-08.
^A. J. Arduengo; E. M. Burgess (1976). "Syntheses and reactions of substituent stabilized thione methylides". J. Am. Chem. Soc.98 (16): 1520–1521.
doi:
10.1021/ja00432a056.
^A. J. Arduengo; E. M. Burgess (1976). "The structure of a substituent stabilized thione methylide". J. Am. Chem. Soc.98 (16): 1521–1523.
doi:
10.1021/ja00432a057.
^A.J. Arduengo "From Hypervalent Compounds to Hypovalent Carbenes", J.C. Martin Symposium: From σ-Constants to σ-Aromaticity (Vanderbilt University, May, 1992)
^C. W. Perkins; J. C. Martin; A. J. Arduengo; W. Lau; A. Alegria; J. K. Kochi (1980). "An electrically neutral σ-sulfuranyl radical from the homolysis of a perester with neighboring sulfenyl sulfur: 9-S-3 species". J. Am. Chem. Soc.102 (26): 7753–7759.
doi:
10.1021/ja00546a019.
^K. Akiba; Y. Yamamoto (1988). "Chemistry of hypervalent organic compounds. Fundamental aspects of hypervalent organic compounds. Characteristic features of structure and reactivity of hypervalent organic compounds of main group elements". Kikan Kagaku Sosetsu. 34: 9–39.
^A. J. Arduengo; C. A. Stewart; F. Davidson; D. A. Dixon; J. Y. Becker; S. A. Culley; M. B. Mizen (1987). "The synthesis, structure, and chemistry of 10-Pn-3 systems: tricoordinate hypervalent pnictogen compounds". J. Am. Chem. Soc.109 (3): 627–647.
doi:
10.1021/ja00237a001.
^D. A. Dixon; A. J. Arduengo; T. Fukunaga (1986). "A new inversion process at Group VA (Group 15) elements. Edge inversion through a planar T-shaped structure". J. Am. Chem. Soc.108 (9): 2461–2462.
doi:
10.1021/ja00269a063.
PMID22175610.
^
abA. J. Arduengo; D. A. Dixon; D. C. Roe (1986). "Direct determination of the barrier to edge inversion at trivalent phosphorus: verification of the edge inversion mechanism". J. Am. Chem. Soc.108 (9): 6821–6823.
doi:
10.1021/ja00281a070.
^
abA. J. Arduengo; D. A. Dixon; D. C. Roe; M. Kline (1988). "Edge inversion barrier at a four-coordinate main group IV center". J. Am. Chem. Soc.110 (13): 4437–4438.
doi:
10.1021/ja00221a067.
^US patent 5272194, A. J. Arduengo, Y. C. Ray, "Process for Preparing a Strengthened Polyimide Film Containing Organometallic Compounds for Improving Adhesion", issued 1993-12-21, assigned to E. I. du Pont de Nemours and Company, Inc.
^US patent 5034464, A. J. Arduengo,, "Amine-Borane Adduct Curing Agents for Epoxy/Anhydride Resins", issued 1991-07-23, assigned to E. I. du Pont de Nemours and Company, Inc.
^US patent 5084542, A. J. Arduengo, P. H. Corcoran, "Epoxy/Isocyanate Crosslinked Coatings Containing 1,3-Disubstituted Imidazole-2-thione Catalysts", issued 1991-01-28, assigned to E. I. du Pont de Nemours and Company, Inc.
^US patent 5091498, A. J. Arduengo, R. J. Barsotti, P. H. Corcoran, "Curable compositions containing 1,3-dialkylimidazole-2-thione catalysts", issued 1993-02-25, assigned to E. I. du Pont de Nemours and Company, Inc.
^US patent 5144032, A. J. Arduengo, "Preparation of Tertiary Amine-Borane Adducts", issued 1992-09-01, assigned to E. I. du Pont de Nemours and Company, Inc.
^US patent 5104993, A. J. Arduengo, "1,3-Dialkylimidazole-2-thione Catalyst and Method for Making Same", issued 1992-04-14, assigned to E. I. du Pont de Nemours and Company, Inc.
^US patent 5182405, A. J. Arduengo, "Preparation of 1,3- Disubstituted Imidazolium Salts", issued 1993-01-26, assigned to E. I. du Pont de Nemours and Company, Inc.
^
abcAnthony J. Arduengo III, Krafczyk Roland (1998). "Auf der Suche nach Stabilen Carbenen". Chemie in unserer Zeit. 32 (1): 6–14.
doi:
10.1002/ciuz.19980320103.
^
abcdA.J. Arduengo "Cars to Carbenes: A Personal Account of Georgia Tech – Molding Futures One at a Time," Georgia Tech's 100 Years of Chemistry Symposium (Atlanta, Georgia, April 19, 2007).
^Cristina Luiggi (2009).
"Taming Carbon's Wild Side". Seed Magazine (November 30, 2009). Archived from the original on December 13, 2009. Retrieved October 6, 2010.{{
cite journal}}: CS1 maint: unfit URL (
link)
^
abA. J. Arduengo; H. V. R. Dias; R. L. Harlow; M. Kline (1992). "Electronic stabilization of nucleophilic carbenes". J. Am. Chem. Soc.114 (14): 5530–5534.
doi:
10.1021/ja00040a007.
^A. J. Arduengo; R. Krafczyk; R. Schmutzler; H. A. Craig; J. R. Goerlich; W. J. Marshall; M. Unverzagt (1992). "Imidazolylidenes, imidazolinylidenes and imidazolidines". Tetrahedron. 55 (51): 14523–14534.
doi:
10.1016/S0040-4020(99)00927-8.
^
abA. J. Arduengo; F. Davidson; H. V. R. Dias; J. R. Goerlich; D. Khasnis; W. J. Marshall; T. K. Prakasha (1997). "An Air Stable Carbene and Mixed Carbene "Dimers"". J. Am. Chem. Soc.119 (52): 12742–12749.
doi:
10.1021/ja973241o.
^A. J. Arduengo; D. A. Dixon; K. K. Kumashiro; C. Lee; W. P. Power; K. W. Zilm (1994). "Chemical Shielding Tensor of a Carbene". J. Am. Chem. Soc.116 (14): 6361–6367.
doi:
10.1021/ja00093a041.
^A. J. Arduengo; H. Bock; H. Chen; M. Denk; D. A. Dixon; J. C. Green; W. A. Herrmann; N. L. Jones; M. Wagner; R. West (1994). "Photoelectron Spectroscopy of a Carbene/Silylene/Germylene Series". J. Am. Chem. Soc.116 (15): 6641–6649.
doi:
10.1021/ja00094a020.
^
abA. J. Arduengo; H. V. Rasika Dias; D. A. Dixon; R. L. Harlow; W. T. Klooster; T. F. Koetzle (1994). "Electron Distribution in a Stable Carbene". J. Am. Chem. Soc.116 (15): 6812–6822.
doi:
10.1021/ja00094a040.
^A. J. Arduengo; M. Kline; J. C. Calabrese; F. Davidson (1991). "Synthesis of a reverse ylide from a nucleophilic carbene". J. Am. Chem. Soc.113 (25): 3625–3626.
doi:
10.1021/ja00025a063.
^
abA. J. Arduengo; H. V. R. Dias; J. C. Calabrese; F. Davidson (1993). "Homoleptic carbene-silver(I)] and carbene-copper(I) complexes". Organometallics. 12 (9): 3405–3409.
doi:
10.1021/om00033a009.
^A. J. Arduengo; H. V. R. Dias; J. C. Calabrese; F. Davidson (1993). "A [carbene germanium diiodide adduct]: model of the non-least-motion pathway for dimerization of singlet carbenes". Inorganic Chemistry. 32 (9): 1541–1542.
doi:
10.1021/ic00061a004.
^
abA. J. Arduengo; S. F. Gamper; J. C. Calabrese; F. Davidson (1994). "Low-Coordinate Carbene Complexes of Nickel(0) and Platinum(0)". J. Am. Chem. Soc.116 (10): 4391–4394.
doi:
10.1021/ja00089a029.
^A. J. Arduengo; S. F. Gamper; M. Tamm; J. C. Calabrese; F. Davidson; H. A. Craig (1995). "A Bis(carbene)-Proton Complex: Structure of a C-H-C Hydrogen Bond". J. Am. Chem. Soc.117 (1): 572–573.
doi:
10.1021/ja00106a082.
^A. J. Arduengo; R. Krafczyk; W. J. Marshall; R. Schmutzler (1997). "A Carbene−Phosphorus(V) Adduct". J. Am. Chem. Soc.119 (14): 3381–3382.
doi:
10.1021/ja964094h.
^
abcdA. J. Arduengo; F. Davidson; R. Krafczyk; W. J. Marshall; R. Schmutzler (1997). "Carbene Complexes of Pnictogen Pentafluorides and Boron Trifluoride". Monatshefte für Chemie. 131 (3): 251–265.
doi:
10.1007/s007060070101.
S2CID96412544.
^A. J. Arduengo; F. Davidson; R. Krafczyk; W. J. Marshall; M. Tamm (1999). "Adducts of Carbenes with Group II and XII Metallocenes". Organometallics. 17 (15): 3375–3382.
doi:
10.1021/om980438w.
^A. J. Arduengo; M. Tamm; J. C. Calabrese; F. Davidson; W. J. Marshall (1999). "Carbene-Lithium Interactions". Chemistry Letters. 28 (10): 1021–1022.
doi:
10.1246/cl.1999.1021.
^A. J. Arduengo; H. V. R. Dias; J. C. Calabrese (1997). "A Carbene•Phosphinidene Adduct: "Phosphaalkene"". Chemistry Letters. 26 (2): 143–144.
doi:
10.1246/cl.1997.143.
^C. A. Stewart; R. L. Harlow; A. J. Arduengo (1985). "Chemistry and structure of the first 10-Sb-3 species". J. Am. Chem. Soc.107 (19): 5543–5544.
doi:
10.1021/ja00305a046.
^C. A. Stewart; J. C. Calabrese; A. J. Arduengo (1985). "Synthesis and structure of the first 20-Bi-9 system: a discrete nine-coordinate 20-electron bismuth". J. Am. Chem. Soc.107 (11): 3397–3398.
doi:
10.1021/ja00297a084.
^M. Yoshifuji; A. J. Arduengo; S. Ito (2008). "Studies on Stable 1,3-Diphosphacyclobutane-2,4-diyls". Phosphorus, Sulfur, and Silicon and the Related Elements. 183 (2 & 3): 335–339.
doi:
10.1080/10426500701734588.
S2CID93271368.
^S. Ito; J. Miura; N. Morita; M. Yoshifuji; A. J. Arduengo (2009). "Catenation of 1,3-Diphosphacyclobutane-2,4-diyl Units Having 2,4,6-Tri-tert-butylphenyl Protecting Groups and a P-sec-Butyl Group in the Ring". Z. Anorg. Allg. Chem.635 (3): 488–495.
doi:
10.1002/zaac.200801265.
^S. Ito; J. Miura; N. Morita; M. Yoshifuji; A. J. Arduengo (2009). "Modeling the Direct Activation of Dihydrogen by a P2C2 Cyclic Biradical: Formation of a Cyclic Bis(P−H λ5-phosphorane)". Inorganic Chemistry. 48 (17): 8063–8065.
doi:
10.1021/ic901072z.
PMID19637863.
^S. Ito; J. Miura; N. Morita; M. Yoshifuji; A. J. Arduengo (2010). "Synthesis and properties of oligo(biradicals) composed of 1,3-diphosphacyclobutane-2,4-diyl units and benzyl-type linkers". Heteroatom Chemistry. 21 (6): 404–411.
doi:
10.1002/hc.20625.
ISSN1098-1071.