Annual R eport 2011
Department
of Chemistry
DEPARTMENT OF CHEMISTRY, NTNU
Høgskoleringen 5, 7491 Trondheim, Norway Phone: +47 73550870
Fax: +47 73550877
E-mail: postmottak @ chem.ntnu.no
Head of Department:
Marie-Laure Olivier
Deputy Head of Department:
Øyvind Mikkelsen
Head of Administration:
Lena Frostad
COVER PAGE
Professor Torunn Berg trawling for plant algaea in the sea in Kongsfjorden at Svalbard.
3
Contents Page
The State of the Department 4 Research Projects
• Simulating CO2 Separation in Molecular Sieve Membranes 5
• The Chemistry Trail in the international year of chemistry 6
• “The chemistry of colours” – Student Exhibition in the Natural Science Library 7
• The Fluoro-organic group: Cancer treatment by inhibition of tyrosine kinases? 8
• Synthetic organic Chemistry - organometallic catalysis 10
• Cultural Heritage: Highlights 12
• The Research Council of Norway´s Special Performance in Oslo Concert Hall 12 Activities
• Scientific publications 13
• Extracurricular activities, conferences and Seminar Attendance 18 Graduate Studies
• Subjects and student attendance 30
• Students 33
Post Graduate Studies
• PhD-projects in progress 34
• MSc in chemistry (MKJ) 36
• MSc in chemistry / Technology (MTKJ) 37
• MSc in education, chemistry (MLREAL) 37
• MSc in environmental toxicology and chemistry (MSENVITOX) 38
• MSc in Natural resources management (MSNARM) 39
• PhD in chemistry 39
• Student exchange to and from NTNU 40
Staff
• Scientific staff 41
• Administrative staff 44
• Technical staff 45
• Scientific assistants 46
• Demonstrators 46
• Guest Professors/Researchers 47
Foreword
4
The State of the Department of chemistry 2011
In 2011 the Department of Chemistry is, for the first time, co-located in one building. Many efforts in the past to unite the Department finally came to a conclusion in 2011. Investments in the range of 15 million NOK ensured that the new laboratories were improved to a standard required for safe handling of chemicals and up to date experimental requirements. The final culmination was a smooth transfer of the organic chemistry group from the Chemistry Building 3 to offices and new laboratories in the Science Building. This marked the end of the extraordinary contribution by many dedicated persons in the Department, making this transfer both smooth and efficient. The result is that the Department now has very good laboratory facilities for all the activities. Although the new laboratories are not spacious at time being, this will be solved when Department of Biotechnology moves out of adjacent laboratories in a couple of years.
In 2009, the Department of Chemistry, among others, was subject to an external review by the Research Council of Norway (Kjemievalueringen 2009). As a follow up, the Research Council announced an Institution-based Strategic Project (ISP) competitive call. In cooperation with Department of Chemical Engineering and Department of Materials Science and Engineering, the Department was granted an ISP within computational chemistry: "From Molecules to Process Applications" with Signe Kjelstrup as project manager. The project joins both theoretical and experimental groups in an effort to further strengthen the overall scientific quality of this important field.
The Department is also involved in many other exciting research projects and both the students and the PhD candidates contribute to enhance the overall scientific knowledge and quality of the work.
Some of these activities are presented in this annual report.
Health, Safety and Environment (HSE) has continued to receive growing attention and several milestones were achieved in 2011. One was the moving of the organic group from Chemistry Building 3 to the Science Building, which significantly improved the standard of the laboratories compared to the abandoned laboratories in Chemistry Building 3. Also, the disposal of many old chemicals, both from the local storages in the laboratories and from the chemical storage room, contributed to improved overall chemical safety. Further, restrictions on the access to laboratories and chemicals, as well as improved routines regarding safety data sheets in the
laboratories, were introduced. As a recognition of her contributions to improve the working conditions, the HSE coordinator at the Department, Nina Klausen, received the NTNU HSE Award at the annual NTNU party on 11.11.11. This is not only a recognition of the dedication of Nina, but also the many others at the Department who have contributed to raise the safety focus at the Department. These achievements were also recognized by the NTNU board when they visited the Department in November 2011.
Among other achievements at the Department, Gøril Aasen Slinde received first price in the competition between students in technology and natural sciences arranged by Tekna and Zero. She presented her work at the ZERO conference in November. Her contribution was based on her thesis work on CO2 storage. Syverin Lierhagen got the overall best results in a Nordic ring test on brines.
The Department seminar was this year focusing on developing a joint strategy for the whole Department. Several challenges still need to be addressed in the coming years. One is the teaching load on the academic staff which needs to be reduced to make room for more research. The Department has a relative low PhD production compared to other departments at the Faculty of Natural Sciences and Technology and more time and efforts should be used to establish research activities and funding for PhD projects.
As a result of the high teaching load on the professors, a process to reduce and streamline a number of courses was initiated in 2011. A good cooperation between the study coordinator and the scientific group leaders resulted in several improvements in the courses offered by the Department. This is considered as a good start to better adjust the number of courses to the teaching capacity.
The year 2011 marks a new turn for the Department and I am looking forward to see the Department grow and develop in the coming years.
Arne Petter Ratvik Acting Head of Department (January- October 2011)
Simula
The pro separatio of carbon Nanoporo promising point of v produce knowledg good me binding, carbon s propose equilibriu (NEMD).
informatio Dynamics describes temperat
Fig.1 The pore repre
Previous hydrogen surface possibility more bou In order aims to (see Fig graphite adsorptio measure along su controlled alone, be this man experime procedur new unde boundary are curre in Chemi
ating CO
2S
duction of c on is of prima n capture and ous, fibrous, g such candi view. In order molecular ge of several i
mbrane functi surface wall tructure and –
to study all m molecula This techni on on adso s or Monte s also the s ure, pressure
real carbon sie esentstions (bot
simulation n on graphite
plays a sur y to create a unded layer.
to compare w study conditio .2 for an illus surface). Clas on isotherms ments are not ch interfaces d “experiment efore combina nner the proje ental results a re of sieve me erstanding of y conditions fo ently being tes cal Engineerin
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and composit
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eferences:
He, X., J.
nergy Procedi Simon, J.M, hem. C, 114 (
the simulatio y in equilibrium arbon membra
temperature namics and s re of CO2/H2.
A. Lie, E. S a 1 (2009) 26
Haas, O.E., 2010) 10212
ons of CO2
m condition on ane. Next we
gradients study transpor
Sheridan, M.- 1
Kjelstrup, S.,
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Research Projects
8
The Fluoro-organic group: Cancer treatment by inhibition of tyrosine kinases?
Introduction
Tyrosine kinases (TK) are enzymes that bind ATP and catalyse the transfer of γ-phosphate to tyrosine residues on proteins, thereby regulating their activity and function. A series of 4-N-substituted 6-aryl-7H- pyrrolo[2,3-d]pyrimidine-4-amines have been synthesised, characterised and tested for their in vitro EGFR (ErbB1) tyrosine kinase inhibitory activity.1
Synthesis
The compounds were prepared by multistep organic synthesis. The main steps are outlined in Scheme 1.1, 2
Scheme 1. Synthetic route to the target compounds.
Twenty six derivatives were synthesised and characterised. Most of the compounds were chiral and produced as their (R)-enantiomers.
Biological testing
All the prepared compounds were tested for their ability to inhibit in vitro EGFR (ErbB1) tyrosine kinase activity. This was done as 10 point titration in duplicates (purchased from Invitrogen) Eight of the new compounds had IC50 values in the range of 2.8- 9.0 nM. Four of these have a fluorine atom positioned at sites otherwise potentially susceptible to oxidative metabolism. Percentage of inhibition plotted towards concentration of some inhibitors is shown in Figure 1.
10000.0 1000.0 100.0 10.0 1.0 0.1 100
80 60 40 20 0
Conce ntration (nM)
% Inhibition
50
R1=H, R2= F R1=p-F, R2=F R1=p-F, R2=OH R1= o-F, R2=OH
Figure 1. Percentage of inhibition plotted against concentration of the inhibitor compound.
The structure activity relationships identified in this study are summarised in Figure 2.
Figure 2. Effect of structural variation on EGFR-TK activity.
The cellular EGFR internalization response of selected compounds was evaluated using HeLa cells. Three fluorinated derivatives had a pronounced effect in inhibiting EGFR internalization (Figure 3).
Figure 3. EGF induced EGFR internalization is potently inhibited by compound 1-4.Subconfluent HeLa cell cultures were starved for growth factors and left untreated or stimulated for 10 minutes with EGF (100 ng/mL, final concentration) in the absence or presence of the indicated compounds (500 nM, final concentration). Immunostained EGFR (green) and DNA (blue) was imaged using a Zeiss Axiovert 200 microscope with a 63X lens and a confocal detector. The images are representative for more than 500 randomly selected and manually inspected cells for each condition.
Docking Prelimina compoun nM, have site. Fig compoun structure substituen the entra minor cha R2-group, aromatic
Figure 4.
TK ATP b 1) is shown
Figure 5.
his work at
Future w
Further b compoun testing to selectivity metabolic modeling The grou kinase synthesis of our ma g
ary docking ds with IC50
e similar confo ure 4 show d 4, super complex nt on the 6-a ance of the b anges in IC50
, whereas th amines at C-4
Compound (R) binding domain,
n in red.
PhD student Sv t ESOC 2011, C
work
biological eval ds is underw owards mutan
y by testing t c studies ,
.
up is also ex inhibitors by s This work is aster and PhD
studies values in the ormations in t ws the docke rimposed wit of AEE-788 ryl group is d inding pocket values upon ere is limited 4.
)-4 (green) doc co-crystallised
vein Jacob Kas Crete.
uation of six way. These nt enzymes a
towards a pa X-ray cryst
xtending the y organic d
aided by the students.
revealed th e range of 3- the ATP bindi ed structure
th the crys 8.3 The pa directed towar t, explaining t variation of t d space for t
ked in the EGF d AEE-788 (Fig
spersen present
of the identifi studies inclu nd cells, kina anel of kinase
allography a
search for n diversity bas dedicated wo
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cknowledged f eferences
[1] Kasperse Fuglseth, Hoff, B. H tyrosine k 6-aryl-7H- J. Med. C [2] Sørum, C
1H,13C a methoxyp amines in (2010) 24 [3] Yun, C.
Greulich, of lung ca complexe into differ (2007) 21 Bår
student Steff s.
udent Svein Jac in Han and Synn
ement essor Eirik Su ofessor Geir B
s is acknowle Anders Ja for financial su
n, S. J., Sø E., Kjøbli, E., H. Synthesis an kinase inhibitory
-pyrrolo[2,3-d]py Chem. 46 (2011)
C., Simic, N., and 19F NMR d phenyl)-7H-pyrro n DMSO-d6, M 4-248.
H., Boggon, T H., Meyerson, ancer-derived E
s: mechanism ential inhibitor s 7-227.
rd Helge Hoff an
fen Bugge ana
cob Kaspersen ne Larsen.
undby (HIST) jørkøy (St. Ol edged for taki ahres found upport.
rum, C., Will Bjørkøy, G., S nd in vitro EGF y activity of 4-N- yrimidine-4-ami ) 6002-6014.
Sundby, E., H data of N-subst olo[2,3-d]pyrimid Magn. Reson.
T. J., Li, Y., W M., Eck, M. J.
GFR mutants a of activation a sensitivity, Can
nd Svein Jacob
alysing his
supervising
is part of avs/HIST) ng on the dation is
assen, V., Sundby, E.,
FR (ErbB1) -substituted nes , Eur.
Hoff, B. H.
tituted 6-(4- din-4-
Chem. 48
Woo, M. S., . Structures and inhibitor and insights ncer Cell 11
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and blood pla ace Elements 26. Suppl. 1 s.
Gioia, Rosa Tripti; Buchel s, Eiliv; Jones, d Distribution European Ba 008? Implicatio nvironmental um 45.(17) s. 7 es, Eiliv; Lierha trace elemen d differences elements. En 2011 ;Volum
S. Milicevic;
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234-S234
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genic atmosph ic: a fracti ry And Physic
health. I:
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conservation y. I: ICOM C
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of PCBs a ackground So ons for Sourc Science a 7291-7297 agen, Syverin nts in rye a s in uptake a vironmental a 70.(2-3) s. 25
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orunn; Dasto Engelsen, O heric mercury onation stud cs 2011 ;Volu
Sustaining s climate chang 470-95857-5.
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profiles on glaciated istry 2011
Tomasz n, Syverin;
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Activities
18
Honours, Extracurricular activities, Participation in Courses, Conferences, Lectures, and Study Visits
B. Alsberg
Section Leader, Applied Theoretical Chemistry Group, Department of Chemistry, NTNU.
ICRM - 5th International Chemometrics Research Meeting, Nijmegen, Netherlands, Sep. 25 – 29, 2011.
Co-Author on Poster Presentation: A Method for rapid Localization of Bone Fragments on Surfaces using Chemical Imaging and Backprojection.
T.N. Andreassen
Kjemiløypa 2011, NTNU, Trondheim, Sep. 26 – 30, 2011.
T. Anthonsen
Conference “26. Organisk kjemisk vintermøte”, Skeikampen, Norway, Jan. 6 - 9, 2011.
Co-Author on Poster Presentation: Antiepileptic Drug (R)-Stiripentol.
COST Action CM0701 Biocatalysis Summer Training School, Siena, Italy, April 27 – May 1, 2011.
Co-Author on Poster Presentation: Kinetic Resolution of Dihalocyclopropyl Alcohols.
Conference “Det 19. landsmøte i kjemi”, Lillestrøm, Norway, Sep. 28 – 29, 2011.
Co-Author on Poster Presentations: ”Femti år med organisk kjemi på NTH, Trondheim 1910-1960.
Bevare historien”, ”Nils Andreas Sørensen (1909- 1987): Professor i Organisk kjemi NTH 1939-1976”,
”Professor Sørensen: Acetylenforbindelser i kurvblomster. UV-spektroskopi 1940-60, så kom NMR til NTH!” and ”Professor Sørensen - Engasjert foreleser og debattant”.
M. Ardelan
Mesocosm Experiment in the Comau Fjord, Chile, Jan. 15 – Feb. 24, 2011.
Research Stay (WAFOW Project) at Dokuz Eylul University, Izmir, Turkey, June 20 – July 18, 2011.
Mesocosm Esperiment (WAFOW Project) at Agdenes, Norway, Sep. 9 – 30, 2011.
Conference “Transatlantic Science Week”, San Francisco, CA, USA, Sep. 25 – 26, 2011.
Co-Author on Lecture on: Underwater Monitoring of Bio-Geo-Chemical Objects of Interest using Underwater Hyperspectral Imagery.
Research Co-Operation with UC Berkeley &
Stanford University and Scripps Institute of Oceanography, California, USA, Dec. 15 – 31, 2011.
F.G. Banica
Referee for the Czech Science Foundation.
XXI International Symposium on Bioelectrochemistry and Bioenergetics, Kracow, Poland, May 8 – 12, 2011.
Co-Author on Poster Presentation: The Study on the Properties of Self-Assembled Bimolecular Layers at Gold Electrode with Incorporated Calixarenes for Catecholamine Detection.
2nd International Conference on Bio-Sensing Technology, Amsterdam, Netherlands, Oct. 10 – 12, 2011.
Co-Author on Poster Presentation: Electrochemical Impedance Spectroscopy for Assessing the Recognition of Cytochrome c by Immobilized Calixarenes.
D. Bedeaux
Visit at ETH Zurich, Switzerland, March 2 – 10, 2011.
Co-Author on Guest Lecture on: Thermodynamics of a Small System in µT Reservoir.
Conference “FISES 2011”, Barcelona, Spain, June 2 – 4, 2011.
Co-Author on Lecture on: Thermodynamics of a Small System in a mu,T Reservoir.
JETC11 Joint European Thermodynamics Conference, Chemnitz, Germany, June 26 – 29, 2011.
Co-Author on Lectures on: “Multicomponent Interfacial Transport as described by the Square Gradient Model”, “Thermodynamics at Small Scales” and “Local Equilibrium for the Gibbs Surface in 2-Phase Multi-Component Mixtures”.
Lorentz Workshop on the Dynamics of Complex Fluid-Fluid Interfaces, Leiden, Netherlands, Sep. 26 – 30, 2011.
Co-Author on Lecture on: The Non-Equilibrium Square Gradient Theory; Non-Equilibrium Thermodynamics for Surfaces and Local Equilibrium.
BIT's 1st Annual Congress of Nano-S&T-2011, Dalian, China, Oct. 23 – 27, 2011.
Co-Author on Lectures on: “The Role of the Temperature in the Nucleation Process” and
“Local Equilibrium for the Gibbs Surface in a 2- Phase Multi-Component Mixture”.
T. Berg Field Wo July 7 an
”Kvikksøl Internet, 24th TFm Jan. 31 – Co-Autho Atmosph Analysis
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elggåten løse Feb. 8, 2011.
kke sør-norsk per ”Smaalene
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nd, Spitzberg 9, 2011.
med sollyset”
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tion, Rappersw .
on: Is it poss tion of hea
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ternet, Feb. 9 Friskere elg i Finnmarken”, F eminar ”Miljø 011.
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Er de norske terview on I arch 6, 2011.
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nord”. Interv Feb. 11, 2011 2015 – III”, NF ortynning av a
Forekomst og e elge påvirk nternet (Dan
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Lecture on: M we know from
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Poster Pres Mercury Co sphere: Why i
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nal Conferenc a, Turkey, Sep
Lecture on etal Depositio of Moss Sampl
at University n. 24 – Feb. 4 18, May 26 – J Sep. 2, Oct. 4
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of Oslo, Depa , March 14 - 2 June 2, June
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Chemistry, July 10 – rrolo- and
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K.L. Bøy Research Radiation Line, Gre Nov. 3, 2 Research Synchrot 2010.
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A. Fiksda Board Me The Rese Board Me (the Grou Chemica Member Selskap ( NTNUs B 2011-.
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Spectroscopy aris, France,
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versity of Peru
KOSK II Res of Norway.
ggruppen for Chemistry) o
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ganisk kjemi Jan. 6 - 9, 20 on: Synthesis cyclic Carbene Presentations:
erocyclic Car
ens Univers 21, 2011.
el Cell 201 8, 2011.
ogen Producti and “Compari alorimeter”.
Wetsus, Cen ter Technolog
– 26, Sep. 5 12 – 22, 2011.
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an Synchrotr Norwegian Bea
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Bekymret for e ewspaper ”Aft Elgen får hels Agderposten”, Elgen i sør sy V; NRK Hedm Nå skal elggå ørlandet, Feb.
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Organome hanghai, Chin Poster Prese f Chiral N-
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elgen i Sør-No tenposten”, Fe esjekk”. Interv Feb. 8, 2011.
kere enn elge mark og Opplan åten løses”. I
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ten løses”. Int 8, 2011.
pargylesters w ns of Propa
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(Norwegian J
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21
”Skal sjekke sør-norsk ”pingle-elg”. Interview in the Newspaper ”Smaalenenes avis”, Feb. 8, 2011.
“Sunnere elg i nord”. Interview in the Newspaper
“Finnmark Folkeblad”, Feb. 8, 2011.
“Helseproblemer hos skogens konge”. Interview on Internet, Feb. 9, 2011.
”Friskere elg i nord”. Interview in the Newspaper
”Finnmarken”, Feb. 11, 2011.
”Er de norske elge påvirket af tungmetaller?”.
Interview on Internet (Danmarks Jægerforbund), March 6, 2011.
47th Eurotox Conference ”Eurotox 2011”, Paris, France, Aug. 28 – 31, 2011.
Co-Author on Poster Presentation: Fatal Pesticides- Related Self-Poisonings in the Southeastern Region of Serbia – Alarming Increase in Suicides Calls for Restrictions.
9th ISTERH Conference: “Trace Elements in Health and Disease: Essentiality, Toxicity”, Belek, Turkey, Oct. 16 – 21, 2011.
Co-Author on Lectures on: “Iron Mobilization using Chelation and Phlebotomy” and “Manganese in CSF and Blood Plasma from ALS Patients”.
O.R. Gautun
Member of NFRs Committee for Marine Bioprospecting and Organic Synthesis.
Conference “26. Organisk kjemisk vintermøte”, Skeikampen, Norway, Jan. 6 - 9, 2011.
Co-Author on Poster Presentations: “Synthesis of new Bis(Oxazoline) (BOX) Ligands for Chiral Catalysts” and “The Preparation of Vinylic Side Chains for Potential Therapeutic Agents against Multiple Myelome”.
Meeting at Norwegian Chemical Society, Trondheim Branch, Feb. 22, 2011.
Guest Lecture: “Nobelprisen i kjemi 2010”.
Exposition at the Library of Science, NTNU, Trondheim, May 23 – June 1, 2011.
Poster Presentation: Nobel Prize in Chemistry 2010.
The 16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS16), Shanghai, China, July 24 – 28, 2011.
Co-Author on Poster Presentation: Studies towards the Synthesis of Potential Selective Inhibitors of Tyrosine Kinase 2.
K.F. Gebremariam
Research Stay at the European Synchrotron Radiation Facility (ESRF), Swiss-Norwegian Beam Line, Grenoble, France, June 21 – 25, 2011.
5th Intensive School on Conservation Science, Marmara University, Istanbul, Turkey, July 19 – 29, 2011.
Presentation of a Poster dealing with the Physico- Chemical Investigation of Ethiopian Paintings.
ICOM-CC 16th Triennial Conference, Lisbon, Portugal, Sep. 19 – 23, 2011.
Co-Author on Lecture on: A Multidisciplinary Approach to Conservation of Rock Art in Honnhammer, Norway.
The Joint ICTP-IAEA School on Synchrotron Applications in Cultural Heritage and Environmental Sciences and Multidisciplinary Aspects of Imaging Techniques, Trieste, Italy, Nov. 21 – 25, 2011.
A. Gerontas
8th International Conference on the History of Chemistry, Rostock, Germany, Sep. 14 – 16, 2011.
Lecture on: The Birth and the first Steps of High Performance Liquid Chromatography in the Laboratories; An Example of the Exchanges between Academia and Industry in the United States of the 1960s.
Conference ”Jahrestagung der DGGMNT in Stuttgart”, Stuttgart, Germany, Sep. 22 – 24, 2011.
Lecture on: From Gas Chromatography to High Performance Liquid Chromatography; a Shift in Chemical Practice in an Era of Change.
K. Glavatskyy
Gas Hydrates Symposium at ACS 241st National Meeting, Anaheim, CA, USA, March 17 – 28, 2011.
Co-Author on Lecture on: Lattice Parameters and corresponding Properties of Methane and Carbon Dioxide Hydrates: Molecular Dynamic Simulations.
JETC11 Joint European Thermodynamics Conference, Chemnitz, Germany, June 26 – 29, 2011.
Co-Author on Lectures on:” Multicomponent Interfacial Transport as described by the Square Gradient Model” and “Local Equilibrium for the Gibbs Surface in 2-Phase Multi-Component Mixtures”.
7th International Conference on Gas Hydrates, Edinburgh, Scotland, UK, July 17 – 24, 2011.
Co-Author on Poster Presentation: Understanding the Stability of CO_2+CH_4 Hydrate from Adsorption MC Simulations.
Lorentz Workshop on the Dynamics of Complex Fluid-Fluid Interfaces, Leiden, Netherlands, Sep. 26 – 30, 2011.
Co-Author on Lecture on: The Non-Equilibrium Square Gradient Theory; Non-Equilibrium Thermodynamics for Surfaces and Local Equilibrium.
