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We started counting January 2. 2007, you are visitor Nr. 

Prof. Michael K. Denk, Curriculum Vitae (COS style)

Denk Research Group

Health & Safety

Lectures (Enrolment)

CHM 231S - Introductory Inorganic Chemistry (121)
CHM 2070 - Structure And Spectroscopy (33)
CHM 331S -Advanced Inorganic Chemistry: Organometallics (55)
CHM 393H - Synthesis Laboratory (22)
CHM 4010 - Chemistry and Industry (8)
CHM 489Y - Introduction to Research in Chemistry (na)
CHM 4620 - Advanced Topics in Inorganic Chemistry (8)
CHM 1209S - Structural Methods in Inorganic Chemistry (9) 
CHM 7110 - Advanced Main Group Chemistry (8)

Research Positions

We currently have openings at the PhD level (2) and MSc. level (1).
All projects are "synthetic" with a computational component (Gaussian, DFT calculations, CBS-Q calculations, NMR-shift calculations).
Applicants should have a good knowledge of the chemical literature, read and write English very well, preferably read German, be familiar with high field NMR and have fun working with challenging compounds.
We have a generous array of grease-free glassware that is steadily resupplied by our excellent glass-blower and 5 workstations running Gaussian caculations. Every student gets a Mac laptop (G4) with all necessary software.

Research Projects

Our two current research areas are interdisciplinary and focus on:

A. Folate intermediates, hydrogenases and hydride transfer reactions under biological conditions.

B. Prebiotic transition metal chemistry

This research has evolved over the last years from our old research projects.

1. Carbenes and their "heavy" relatives (R2M: with M = C, Si, P+, Ge, Sn and transition metals).
2. Stabilization of highly reactive species through bulky amido substituents.
3. Synthesis of novel volatile compounds as CVD precursors for microelectronic materials
4. Generation of Ge-Si and Ge-C thin films for semiconductor and solar cell technology, synthesis of new precursors for electronic grade thin silicon films.
5. Generation of superhard, oxidation resistant films based on boron and titanium.


Authors / Title / Journal / Total Citations 2478 (May 2016) 1157 (Aug 2005)


Denk, M.K.; Zheng, Feng-Lan, Hezarkhani Azardokht
A Convenient Synthesis of N-Ethylenimines


Denk, M.K.
The Variable Strenght of the Sulfur-Sulfur Bond, Denk, M.K., Eur. J. Inorg. Chem. 2009, 1358-1368.
Citations: 13


Denk, M.K.: Ye, Xuan
Isothioures - Thioureas - A CBS-Q Study


Denk, M.K.; Zheng, Feng-Lan, Hezarkhani, Azardokht
Steric and Electronic Effects in the Dimerization of Wanzlick Carbenes: The Alkyl Effect
Eur. J. Inorg. Chem. 2007, 3527-3534.

The steric and electronic influence of N-alkyl substituents on the dimerization energies DG° of Wanzlick carbenes (imidazolidin-2-ylidenes) was investigated experimentally and through DFT methods for a series of non-symmetrically substituted Wanzlick carbenes. A series of 3-alkyl-1-tert-butylimidazolidin-2-ylidenes with decreasing steric demand of the alkyl substituent (isopropyl, ethyl and methyl) were obtained in four steps from the commercially available N-alkylaminoethanol compounds. The carbenes are hydrolytically sensitive, colorless oils that can be distilled without decomposition and show no sign of dimerization to the respective enetetramines, even after prolonged heating. Calculations at the B98/6-31G(d) level confirm that the dimerization of all three carbenes is thermodynamically unfavorable. To separate the steric and electronic stabilization of Wanzlick carbenes by N-alkyl substituents, the formation energies of R,H3 mono-alkyl enetetramines were used to derive electronic increments for the N-alkyl substituents. The computational data show that all alkyl substituents electronically stabilize Wanzlick carbenes vs. their dimerization products with increments ranging from 2.97 kcal mol-1 (N-methyl) to as high as 6.28 kcal mol-1 (N-tert-butyl). For combinations of N-methyl, N-ethyl and N-isopropyl substituents, the increments are additive and the dimerization energies were found to be free of noticeably steric effects. Significant steric strain was found for all tBu-substituted carbenes with strain energies of the dimerization products ranging from 6.92 kcal mol-1 [formation of (E)-Me2tBu2-enetetramine] to 24.23 kcal mol-1 (formation of tBu4 enetetramine). The tert-butyl substituent thus assumes a unique position by strongly stabilizing the carbenes electronically as well as sterically.

Citations: 23


Denk, M.K.;Ye, Xuan
Alkylation of Ethylenehiourea with Alcohols: A Convenient Synthesis of S-alkyl-isothioureas Without Toxic Alkylating Agents,
Tetrahedron Letters 2005, 46, 7597-7599.
Citations: 5


Denk, M.K.; Hezarkhani, A.
A. "The Thermodynamic Satbility of P8 - A CBS-Q Study
Heteroatom Chemistry 2005, 16, 453-457.
Citations: 6


Denk, M.K.; Krause, M.; Niyogi, D.F.; Gill, N.K. "Reaction of 1,2-dibromoethane with primary amines - formation of N,N'disubstituted ethylendiamines and homologous polyamines H-[N(R)-CH2CH2]-NHR" Tetrahedron, 2003, 59, 7565-7570.
Citations: 11


Denk, M.K.; Gill, N.K.; Singh, G. "Potential explosion hazard of alpha-lithiated amines", C & E News, June 30, p2, 2003.


Hui Zhou, Y.; Denk, M. K.; "A New One-Step Three-Component Synthesis for Selenoureas" Tetrahedron Lett., 2003, 44, 1295-1299.
Citations: 13


Denk, M. K.; Hatano, K.; Lough, A. J. "Synthesis and Characterization of a Carbene-SO2 Adduct8" Eur. J., Inorg. Chem. 2003, 224-231.
Citations: 14


Denk, M. K.; Gupta, S.; Brownie, J.; Tajammul, S.; Lough, A. J. "CH Activation with Elemental Sulfur (I): Synthesis of Cyclic Thioureas from Formaldehyde Aminals and S8" Chem. Eur. J., 2001, 7 (20): 4477-4486.
Citations: 25


Hitchcock, A. P.; Ennis, L. E.; Lehmann, J. F.; Denk, M.K., "Transient ISEELS: a new probe of chemical reactions" J. El. Spec. 2001, 114, 1037-1041.
Citations: 4


Denk, M. K.; Rodezno, J., Gupta, S.; Lough, A. J. "Oxidation, Hydrogenation And Hydrolysis of Stable Diamino Carbenes" J. Organometal Chem. 2001, 617-618, 242 - 253.
Citations: 94


Leites, L. A.; Bukalov, S. S.; Denk, M. K.; West, R.; Haaf M., Raman Evidence of Aromaticity of the Thermally Stable Silylene (tBuNCH=CHNtBu)Si:" J. Molecular Structure - THEOCHEM, 2000, 550, 329-335.
Citations: 12


Published twice by editorial error:
Denk, M. K.; Rodezno, J., Fast deuterium labeling and the basicity of stable diamino carbenes (imidazole-2-ylidenes) J. Organometal. Chem. 2000, 608, 122-125.
Citations: 24
Denk, M. K.; Rodezno, J., Fast deuterium labeling and the basicity of stable diamino carbenes (imidazole-2-ylidenes) J. Organometal. Chem. 2001, 617-618, 737 - 740.
Citations: 28


Denk, M. K.; Gupta, S.; Ramachandran, R. "Aromatic Phosphenium Cations" Eur. J. Inorg. Chem. 1999, 41 - 49.
Citations: 59


Denk, M. K.; Hatano. K.; Ma, M.. J. "Nucleophilic Carbenes and the Wanzlick Equilibrium - A Reinvestigation" Tetrahedron Lett. 1999, 40, 2057 - 2060.
Citations: 25


Lehmann, J. F. ; Urquhart, S. G.; Ennis, L. E.; Hitchcock, A. P.; Hatano, K.; Gupta, S.; Denk, M. K. "Core Excitation Spectroscopy of Stable Cyclic Diaminocarbenes, -Silylenes, and -Germylenes " Organometallics 1999, 18, 186- 1872.
Citations: 61


Haaf, M.; Schmiedl, A.; Schmedake, T. A.; Powell, R. A.; Millevolte, A. J.; Denk, M. West, R. "Synthesis and Reactivity of a Stable Silylene" J. Am. Chem. Soc. 1998, 120, 12714 - 12719.
Citations: 137


Denk, M. K., Khan, M., Lough, A. J., Shuchi, K. "Redetermination of the Germanium Dichloride complex with 1,4-Dioxane at 173K". Acta Cryst. 1998, C54, 1830 - 1831.
Citations: 22


Denk, M. K.; Hatano, K.; Lough, A. J. "Reactions Between Stable Carbene Analogues - Oxidation of a Stable Silylene by Tin(II)chloride" Eur. J. Inorg. Chem. 1998, 1067-1070.
Citations: 31


Urquhart, S. ; Hitchcock, A. P. ; Lehmann, J.F.; Denk, M. K. "Probing Delocalization In Stable Silylenes: Core Excitation Spectra of Si(NRCH=CHNR), Si(NRCH2CH2NR), H2Si(NRCH=CHNR) and H2Si(NRCH2-CH2NR), (R= tBu)." Organometallics 1998, 17, 2352 - 2360.
Citations: 32


Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. "The Steric Stabilization of Nucleophilic Carbenes" Angew. Chem. Int. Ed. Engl. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719 - 2721.
Citations: 64


Denk, M.K.; Gupta, S.; Ramachandran, R. "Aromatic Phosphenium Cations" Tetrahedron Lett. 1996, 9025 9028.
Citations: 141


Metzler, N.; Denk, M. K. "Synthesis of a Silylene Borane Adduct and its slow Conversion into a Silylborane", Chem. Commun. 1996, 2657 - 2658.
Citations: 43


West, R.; Denk, M. "Stable Silylenes: Synthesis, Structure, Reactions" Pure & Appl. Chem. 1996, 68 , 785 - 788.
Citations: 160


Denk, M.; Aromatic Silylenes and Phosphenium Cations Abstr. Pap. Am. Chem. Soc. S 209: 163-INOR Part 1 Apr 2 1995.


Arduengo, A.J.; Bock, H.; Chen, H.; Denk, M.; Dixon, D. A.; Green, J. C.; Herrmann, W. A.; Jones, N. L.; Wagner, M.; West, R. "Photoelectron-spectroscopy of a Carbene/Silylene/Germylene series, J. Am. Chem. Soc. 1994, 116, 6641 - 6649.
Citations: 274


Denk , M.; Lennon, R.; Hayashi, R.; West, R.; Haaland, A.; Belyakov, A. V.; Verne, H. P.; Wagner, M.; Metzler, N. "Synthesis and Structure of a Stable Silylene" J. Am. Chem. Soc. 1994, 116, 2691 - 2692.
Citations: 448


Denk, M.; Hayashi, R. K.; West, R. "Reaction of a Stable Silylene with Covalent Azides - A New Synthesis for Silaimines" J. Am. Chem. Soc. 1994, 116, 10813 - 10814.
Citations: 74


Denk, M.; Green, J. C.; Metzler, N.; Wagner, M. "Electronic Structure of a Stable Silylene: Photoelectron Spectra and Calculations" J. Chem. Soc., Dalton Trans. 1994, 2405-2410.
Citations: 91


Denk, M.; Hayashi, R. K.; West, R. "Reaction of a Stable Silylene with Ni(CO)4 "Silylene Complexes from A Stable Silylene and Metal Carbonyls - Synthesis and Structure of [Ni(tBuN-CH=CH-NBut)Si)2(CO)2], a Donor-Free Bis-Silylene Complex" J. Chem. Soc., Chem. Commun. 1994, 33-34.
Citations: 117


Denk, M.; A stable Silylene, Synthesis Structure Reactivity. Abstr. Pap. Am. Chem. Soc. S 207: 49-INOR Part 1 Mar 13 1994.


Herrmann, W. A.; Denk, M.; Scherer, W.; Kleine, M. "Volatile Boranate Complexes of Titanium and Zirconium " J. Organomet. Chem. 1993, 444, C21 - C24.
Citations: 46


Herrmann, W. A.; Anwander, R; Denk, M. "Neodym and Yttrium Alkoxides with Bulky Chelate Ligands" Chem. Ber. 1992, 125, 2399 - 2405.
Citations: 37


Herrmann, W. A.; Bogdanovic, S.; Behm, J.; Denk, M. "Methyl Nitridomolybdenum(VI) Complexes " J. Organomet. Chem. 1992, 430, C33 - C38.
Citations: 35


Herrmann, W. A.; Denk, M.; Behm, J.; Scherer, W.; Klingan, F.-R.; Bock, H.; Solouki, M.; Wagner, M. "Stable, Cyclic Germylenes: Synthesis, Structure, Metal Complexes, Thermolytic Studies " Angew. Chem. 1992, 104, 1489 - 1492; Angew. Chem. Int. Ed. Engl. 1992, 31, 1485-1488.
Citations: 240


Herrmann, W. A.; Denk, M.; Härter, P.; Dyckhoff, F.; Huber, N.; "Novel Hard Coatings from the Decomposition of Metal-Organic Compounds" Dünnschichttechnologien ´92, VDI-Verlag GmbH, Düsseldorf, 1992.


Herrmann, W. A.; Denk, M.; Albach, R.; Behm, J.; Herdtweck, E. "Cyclic Metal Amides " Chem. Ber. 1991, 124, 683 - 689.
Citations: 54


Herrmann, W. A.; Huber, F.; Härter, P.; Denk, M.; Dyckhoff, N. "Volatile MN4-Complexes with Dimethylsilyl Substituents " Chem. Ber. 1992, 125, 117-118.
Citations: 8


Herrmann, W. A.; Denk, M;. Dyckhoff, F.; "Niobium and Tantalum Complexes with Imido Ligands" Chem. Ber. 1991, 124, 2401 - 2403.
Citations: 7





Denk, M. K.; Fournier, S. "Volatile Amidinates and their Use in CVD." This invention has been disclosed to the University, patent pending. The process allows the chemical vapor deposition of thin copper films under chloride and oxygen free conditions and may be of significant importance to the manufacturing of microelectronic devices.


US Pat. 5,728,856. "Silylene, A Process for Its Production And Its Use" Inventor: Denk, M.K., (1996)


German Patent 42 14 281.4 - Co 9201. "Procedure for the Synthesis of Germaniumdichloride Ether Adducts". Inventors: Denk, M.; Herrmann, W. A, patents pending in the U. S., Japan, Korea and the EC (1994).


German Patent 42 34 998.2. "Chemical Vapor Deposition of Germanium from Cyclic Germanium Amides". Inventors: Denk, M.; Herrmann, W. A., patents pending in the U. S., Japan, Korea and the EC (1993, 1999).


Ger. Pat. 43 16 883 A1. "Synthesis of Stable Silylenes by Reduction Processes". Inventor: Denk, M., (1994)


Funding History

$ / Period

Premiers Research Excellence Award

5 years
$ 150,000

Electronic Materials

NSERC Equipment Grant

$ 56,000

Dual Train Inert Gas Glove Box

NSERC Major Installation Grant a

$ 840,000

500 MHz NMR Instrument

NSERC Equipment Grant

$ 182,000

GC-MS Instrument with full CI Capability


$ 100,000

Hard Coating of Welding Tools

NSERC Operating Grant

$ 34,500 / y

Amides of Divalent Silicon And Germanium As Precursors For Advanced Materials

NSERC Operating Grant


$ 34,500 / y

Amides of Divalent Silicon And Germanium As Precursors For Advanced Materials

NSERC Operating Grant

$ 42,500 / y

Amides of Divalent Silicon And Germanium As Precursors For Advanced Materials

NSERC Operating Grant

$ 31,500 / y

Amides of Divalent Silicon And Germanium As Precursors For Advanced Materials

NSERC Operating Grant

‘95 - ‘97
$ 30,000 / y

Amides of Divalent Silicon And Germanium As Precursors For Advanced Materials

Provosts Innovative Courseware development Fund

$ 9,600

The Virtual Laboratory III

Provosts Innovative Courseware Development Fund

$ 6,000 / 1 y

The Virtual Laboratory II

Connaught Matching Grant

$ 30,000 / 3y

Solar Cells And New Routes To Semiconductor Thin Films

Provosts Innovative Courseware Development Fund

$ 12,000 / 1y

The Virtual Laboratory I

Connaught Starter Grant

$ 6,000


Humboldt Fellowship
(Fedor Lynen-Program)
$ 45,000 / y

Stabilization of Silylenes

Current Group Members

Past Group Members

Collaborators Past And Present

Contact Information

Dr. Michael K. Denk, Associate Professor of Chemistry
University of Guelph, Guelph, Ontario
Canada N1G 2W1
Tel: (519) 824-4120 x 3820
Fax: (519) 766-1499
Directions: McNaughton Building, Office 334




Patent Information

revised: April 30, 2016