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(AV17658) The Iowa State Presidential Lectureship on Chemistry

(AV17658) The Iowa State Presidential Lectureship on Chemistry


good evening thank you all for coming
tonight welcome to our sixth presidential
lecture in chemistry first of all I’d like to thank president Jeffrey for
making this possible presidential freeze here in the audience tonight it’s
extremely important for us to have the seminars seminar series no university
can claim to be great or even good if it doesn’t have a strong vibrant seminar
series to inspire students to stimulate its faculty and to educate the general
public and it’s very important to have this and again I think president Jeffrey
for making this possible so at this time I’d like to invite
professor John Burke aid University professor in chemistry to come to the
podium and introduce tonight’s speaker Thank You Jake it is indeed an honor to
introduce our 2011 presidential lecturer Professor Richard Royce Shrock Nobel
laureate now I believe our speakers parents might have known something when
they named Richard Royce Schrock because they named him most appropriately
Richard comes from old German meaning powerful leader Royce comes from old
German meaning famous and schrock is the name of a place near Marburg Germany
called Shrock except they put an umlaut over the oh and it becomes shirk so he
would be known as a powerful and famous leader in chemistry from stroke now
professor schrock was born in 1945 in Baron a small farming community in
northeast Indiana for professor shocks eighth birthday he received a chemistry
set from his older brother Theodore and since young Richard was very learned in
the area of carpentry which he learned from his father who was a carpenter it
for his trade Richard constructed in a room in his
house a small laboratory which also had a lot of shelving for his growing
collection of test tubes and flasks and beakers now Richard really liked testing
recipes for mixtures mixtures of various kinds including fiery ones but only once
only once was it necessary to call the local fire department
to put out a fire from one of those fiery experience experiments now in his
address tonight professor schrott may elaborate on the circumstances
surrounding that fiery experiment and he may not I don’t know in 1958 his family moved to California
and in 1967 he received his BA degree from the University of California at
Riverside then he went to Harvard where he received his PhD in 1971 with John
Osborn and then he went to Cambridge now that’s not Cambridge Iowa that’s
Cambridge in England for a year funded by a very prestigious National Science
Foundation postdoctoral fellowship and he went to work with Sir Jack Lewis
professor schrock then took a job at du Pont’s central research department in
the days when they used to do a lot of academic and fundamental research during
a scientifically very creative and fruitful three-year stint at DuPont
professor schrock’s extraordinary research prowess became a subject of
some attention by Barry Sharpless who was a professor of chemistry at MIT at
the time and in fact as a result of that interaction professor schrock received
an invitation to the dicapta to join the chemistry department at MIT in 1975 and
at MIT he was promoted to full professor in only five years in 1989 he became the
Frederick G Keyes professor of chemistry in 205 professor Schrock won the Nobel
Prize in Chemistry which he generously shared with Yves Shillong of the French
petroleum in in stitute and with Bob Grubbs at Caltech
in addition to the Nobel Prize professor Shrock has won many other prizes awards
and honors and I’ll mention only a few an Alexander von Humboldt award in 1995
the American Chemical Society Award in inorganic chemistry in 96 the Baylor
medal in 1998 and the COPE Scholar Award in 201 the Sir Geoffrey Wilkinson
lectureship and medal in 200 – the Sir Edward Frankland Frankland prize
lectureship in 204 and the F Albert Cotton award in synthetic inorganic
chemistry in 1996 sorry 206 he’s an elected member of the
American Academy of Arts and Sciences and also a member of the National
Academy of Sciences he was associate editor for The Journal called
organometallics published by the American Chemical Society and that was
for eight years he has published over 500 research publications now in the
metric system that’s 500 milli Gilman’s because professor Gilman had over a
thousand publications throughout the course of his career however I’m sure
professor Rock’s career is by no means over yet now professor schrock has many
research accomplishments and I’m only going to mention one besides the fire in
his house a goal of chemists for the past halves half a century at least has
been the achievement of a cheap and efficient way to make ammonia simply
from atmospheric nitrogen and hydrogen and that’s not a very cheap process to
do at the present time but in 200 3 professor schrock made an astonishingly
large toward that goal and he did that by
demonstrating for the first time that by building a carefully constructed
molybdenum compound as a catalyst atmospheric nitrogen gas could be
converted to ammonia in good efficiency and yield by using hydrogen ions very
simple ions and electrons and that was occurring for him in his laboratory
under very mild conditions atmospheric pressure and room temperature now in
nature certain bacterial enzymes in the soil convert nitrogen compounds to
ammonia and professor schrock’s results suggest that a single molybdenum Center
in nitrogenous enzymes may be the catalytic site at which nature performs
that marvelous reaction of converting nitrogen to ammonia and of course
ammonia is as we all know a primary fertilizer for farm crops professor
schrock professor joffrey and professor petrodes would you join me at the podium
here for presentation – professor schrock the commemorative plaque of his
presidential lecture which is entitled a lifetime of chemistry reflections of a
Nobel laureate and by the way Richard the cheque is probably in the mail okay is this working yeah it seems to be
working you hear me back there okay thank you very much for those wonderful
comments John it’s a nice outline of my talk or at least the personal side of it
that I’m going to talk about in the beginning here and it’s great pleasure
I’ve known Professor George for a number of years great in organic chemists I
asked him if he does any chemistry anymore he says occasionally he thinks
about it but he has other problems I know that so this is a public talk as
you well know so it’ll be a little light on the chemistry tomorrow will be a
technical talk which will be a little heavy on the chemistry light on the
other things I hesitate to show this first picture because my mother hated it
and but it gives me some pleasure to show you where I came from and it’s it’s
it’s an interesting one that’s Decatur Indiana so I was born in Bern indicators
about 13 miles south Bern and my parents left Bern when I was born
not because I was born but for other reasons that I won’t go into and moved
to Decatur and that’s where I grew up until I was 14 or so and since that’s
the summer of 46 this is me right there and that’s Ted my
five year older brother he’s the one who gave me the chemistry set and this is
Luther 10 years older my mother and father and my mom hated this picture
because she said it made us look poor and well we weren’t poor but we weren’t
rich either so as John said I moved to California when I was 14 and went to
Mission Bay High School I was there for half a year in junior high school and I
continued my science that he a little bit about this is a contest a science contest in San Diego that I won
some prize for you see there for the effects of osmosis on sea urchin eggs
and went out and got the sea urchins myself caught him up got the eggs and
did all the work and appeared in a newspaper there doing my my work that
you can’t see the date but that says February 1961 so I was a junior in high
school at that time and so I continued my science through high school I never
thought I would do anything but continue my interest in chemistry and I went to
Riverside learned a lot at Riverside I worked for a man named James Pizza was
an atmospheric chemist I did a lot of infrared studies of what was in the
atmosphere as we knew it back then I built a vacuum line learned how to glass
blow and really learned a lot and that was my first summer in 1968 that would
have been and I studied for every year and every summer thereafter before I
went to Harvard here’s a picture of me you can’t see it maybe but then I’m
smoking a pipe and I thought I thought it would make me smarter but it really
didn’t have much effect so I stopped doing that a number of years ago but I
thought it was cool at the time so at Harvard as John mentioned I worked for
John Osborne and I don’t know if you can see that picture maybe it’s impossible
to dim any of the lights up front here so that that was the group at the time
we had a great deal of fun John was a good friend my whole life and as I
mentioned at the end he passed away 11 years ago now of a brain cancer at the
age of 60 one other thing I did when I was at
Harvard as I met my wife Nancy and this is 1969 I met her married her in 1971
just before I went to Cambridge England to do a postdoc here we are coming back
from Cambridge England I’m all natty and my sweater and everything and we bought
a couple of bicycles hers has been sacrificed for my son and mine I still
have and ride believe it or not I mean it’s not a great bike but you know it
it’s a bike and I think they were 67 pounds apiece which was about $150 at
the time then I went to DuPont John mentioned in 1971 there were no jobs
that’s why I went to England as a postdoc 1972 the situation wasn’t much
better but I managed to meet a guy named Earl munities in Cambridge and her
immunity’s was one of the six associate directors at DuPont oh I can move around
oh good yeah thank you very much Marilyn immunity’s is one of the associate
directors at DuPont and he sort of interviewed me and he said well do you
want a job and I said sure so I took that job at DuPont which was as John
mentioned a real research department and that’s when you you could do what you
wanted there for three years or so before you had to do something useful
but sometimes you what you tried to do turned out to work and what DuPont did
at the time and still does is of course make polymers and so my my charge was to
make some new polymerization catalyst so I learned about catalyst from John
Osborne I studied some rhodium chemistry and rhodium is in this periodic table
which I assume you all know by heart rhodium is right here in group nine and
over here is in the what we call the early metals group four and five is
titanium which would make make polymers in vanadium zirconium and chromium
things like polyethylene polypropylene and so my my proposal it was a very
simple proposal to my group leader George partial was to study the
organometallic chemistry of tantalum down here so nobody had done that at
least I didn’t know of anybody having done that I found out later fortunately
that somebody had begun that that’s really what started me on my research
career and I’ll tell you about that and then I’m highlighting right next door in
group six molybdenum element 42 that’s the answer to life the universe and
everything and tungsten right below it so these are the elements along with
rhenium a little bit that have really comprised what my career is all about
and then this is the the question for the scientists in the audience anybody
recognize who that is that’s was CEO he joined this was as a graduate student at
Indiana University he was my lab mate a DuPont guy named Fred tabby that’s Fred
Terry entering graduate school at Indiana University he passed away in
1996 of pancreatic cancer he was a heavy smoker and didn’t bother about benzene
and such and I don’t know whether they had that effect but that’s a fact so
yeah that’s a picture of Fred Debbie he was a great chemist and I learned a lot
from him a lot about metal carbon bonds metal
carbon bonds that’s what organometallic chemistry is
all about which is more or less what what I’ve done my whole life so Fredman
was my lab mate Jeff Wilkinson who received a Nobel
Prize in 73 was a consultant they still had consultants at places like – Pont
back then and so these great men would come through and they would you’d get a
chance to sit down with them and tell them what you were doing and I did that
or actually I went to a lecture where he talked about this compound here so this
is tungsten this is that metal at the bottom of group six and it has the
possibility of putting six things around it six anions as we call them these
methyl groups so these are six methyl groups around tungsten he showed and
that he could make that he did make it he characterized it in 1973 summer of
1973 was when he gave that talk or maybe it was a little earlier in the spring to
us DuPont I thought that was wonderful I was beavering away and in tantalum
chemistry but I I could put two and two together I figured well if Thompson’s in
group six and tantalum is in group five maybe I should put five of those methyl
groups around tantalum that would be a good I’ll go back to this one all right so
that’s what I tried to do Jeff Wilkinson in his Nobel address you
have to give a talk when you give it a get a Nobel Prize and he said down below
here pendimethalin to lamar Schrock DuPont Wilmington private communication
has recently been synthesized because he had written about hexamethylene in the
know valve address thank you still working on that’s what I
try to do and fortunately this man yeah well trade you here is this one working
ah thank you so a man named Juvenal somebody I’ve never heard of since
and didn’t know at the time who was at the Jet Propulsion Laboratory in
Pasadena for some reason had made tri methyl tantalum dichloride so all I had
to do is replace two methyl groups with or two chlorides here Co minus groups
with methyl groups and make Penta methyl tantalum I show one of them expanded
here’s carbon has four things bound to it one bond to the metal and three bonds
to H’s and that’s what I did it however unlike hexa methyl tungsten was quite
unstable and decomposed above where ice melts at zero degrees and decomposes in
what was called a biomolecular fashion so two of these molecules while there’s
a whole bunch of them but they they would run bonds collide with each other
and decompose in a way I won’t go into detail about which I studied but in
order to prevent that by molecular decomposition I just put it put a big
other group in place of one of these H’s I put another carbon with three methyls
on it so this is called neopentyl pent for five neo is the shape of this ligand
and I tried to make Penta neopentyl tantalum
so that seems like a logical sort of thing to do and I was having fun I
didn’t have to make polymers at least in my first three years and I tried to do
that and fortunately it failed now that’s I say that because a lot of
things are fortunate to fail because you find that you’d make a discovery so this
is the Eureka moment when I tried to make this Penta neopentyl tantalum which
probably is an intermediate in the reaction what happened is it decomposed
intramolecularly it didn’t run into another molecule it’s too big and bulky
but it what it it one of these neopentyl took an h from a neighboring neopentyl
and made what we call neopentane and then created a carbon metal double bond
so this was there’s no four bonds to carbon now a double bond to the metal
this was a new type of compound for various reasons
that’s called a high oxidation state alkyl Adeem or carbine complex and that
was published in 1974 this is an unusual compound because it
has this big these big bulky groups on it it’s a very stable towards this by
molecular decomposition and in fact you can distill it like like you would water
at a low pressure and a temperature of about 75 degrees very very surprising
for a brand new exciting compound like this well why do I tell you this because
the double bond the metal carbon double bond is a very important feature of
everything I do these days and this was where it all started and because there
was a lot of talk in the air about a new reaction that had been discovered at
DuPont curvaceously enough in about 1956 and in order to preface that reaction I
want to talk about I want to tell you that carbon-carbon double bonds are
things that have carbon-carbon double bonds in them called olefins or alkenes
there’s another name for them don’t get mixed up they’re pretty stable compounds
carbon compounds are stable you know in general your you’ve got a
lot of them in you of course and alkenes are in oil they’re very stable and you
can burn them and so on they don’t they don’t get mixed up these double bonds
the blue parts here and in this olefin and the red parts the blue and red don’t
get mixed up it’s a little political here they don’t they don’t form the
Republican Democratic one here they remain in their camps so that doesn’t
happen or at least they did it wasn’t known to happen because there’s no
pathway for that reaction there’s no mechanism as we call yet there’s no
there’s no allowed way for that to happen except a guy named as I just
mentioned a DuPont herb eleuterio in 1956 showed that that was probably not
the case so he took a mixture of these blue and red all offense and found that
he did make the mixed one only in the presence of a catalyst so only when you
prepare only when you add catalyst that allows the the mechanism of that
reaction to take place can it happen it can’t happen in the absence of the
catalyst the catalyst is not used up but over and over does this same reaction
switches the blue and the red parts of olefins now Eve Chauvin John mentioned
was third recipient of the Nobel Prize in 2005 was the one who first wrote down
the correct mechanism for that reaction and that reaction involved without
knowing what else was on the metal certainly a metal carbon double bond of
an unknown type all the ones that were known at the type wouldn’t do that
reaction and they’re called Fischer carbines who have also received a Nobel
Prize in 73 with Wilkinson so he wrote down it has to be some metal carbon
double bonded species and it has to react to form a ring and then now you’ve
put a blue and a red carbon together and you can take that
mixed olefin off you make a new carbine it goes around again and reacts and
produces the all the mixed species and gets back to the original blue one so
it’s a two-step process 1/2 of carrying out with time
that scrambling reaction so it was interesting to have just made a new
metal carbon double-bonded species of an unknown type and so I could figure that
one out maybe I should study that reaction for tantalum which I did when I
went to MIT in 1975 let me just show you in which we call human terms how that
reaction works so this is always a little fun so this is it’s kind of like
a square-dance so this is the catalyst the lady in black here and that’s the
original carbon the orange and here are the blue and red olefins you can tell
the relevance because they’re holding hands like that and so that that’s the
initial metal carbon bond and she goes and she she finds either a blue or a red
couple and she found a red couple and in forms a ring so there’s the ring so now
she takes her red partner and goes and finds I think a blue couple and you form
the mixed olefin here which she does there’s and didn’t quite make the ring
there but she does eventually and that’s how the olefins get all mixed up so you
see that most of them are mixed up here there’s still an initial couple there
but that bet that happens all very very very rapidly we’re talking about not the
speed at which you see it here it’s it’s sometimes in seconds these things happen
so a very great speed what we call diffusion control in liquids the rate at
which molecules can just move through liquids so I spent about 10 years then
at MIT really studying tantalum chemistry and figuring out how to make
similar kind of compounds that contain molybdenum that answer to life the
universe and everything or tungsten actually tungsten came first and then
molybdenum and they were all of this type in general the only piece you have
to know about really is this metal carbon double bond that’s the piece that
does all the work there’s a t-butyl group as a carbon with
three methyl groups on it if you remember this is called an amide o group
you can put various kinds of metal nitrogen double bonded species on there
these don’t react these double bonds only those double bonds and then what we
call alkoxides to change the nature of this species and really allow you to do
all kinds of metastasis reactions and get different results now all of these
compounds are sensitive to air and water so you can’t work with them out in the
air you have to work under dinitrogen in – or argon or some other inert gas now
as bob groves in 1992 along with Gregg fou Gregg who is now my colleague at MIT
he was a postdoc with Bob Grubbs at the time along with a number of other people
who were interested in the possibility that these new compounds that I had made
now of molybdenum and tungsten would in fact do this metathesis reaction I had
showed that they would do this reaction these were discovered in 86 so between
80 75 and 86 or 87 I worked on tantalum then for 10 years more or less people
studied these compounds I studied them heavily and Bob Grubbs was the one who
has really had the foresight to see how they could be of use to organic chemists
now it’s not for those chemists of you in the audience if you think about it a
little bit it’s not that easy to make a carbon-carbon double bond it’s a lot of
work and most of the in fact all of the reactions are not catalytic their
stoichiometric which means you build up a lot of byproducts and you have to
dispose of them and so on the beautiful thing about this reaction
is you start with double bonds and you make double bonds this one you don’t
care about that’s this four-carbon piece called butene
and then a carbon-carbon double bond and you make a ring it’s a very nice clean
slick way to make carbon-carbon bonds in organic molecules pretty simple once
initially this one this one this is seven membered ring I think there’s a
six membered ring rings so there are rings that must contain double bonds in
what we call the sis configuration or both of these other bonds carbon carbon
bonds on the same side of that double bond I’ll talk about the other
configuration later so-called trans configuration but this demonstrated that
you could make simple organic molecules from from simple other molecules having
two double bonds in them using these metathesis catalysts so they’re they’re
clean fast no unwanted byproducts and can be done simply done simply in any
other way in 1996 so this is really at the end of the what I call the second
generation catalyst or first generation catalyst period between 87 or so and 80
and 96 or 97 Amir havedo at Boston College here in 95 published a another
paper really the first paper that made an even more complicated molecule a
natural product so organic chemists love to make natural products at least some
of them do and they’re always looking for new ways to do that and these are
drugs they can be they can be lots of things usually it’s an anti tumour agent
a drug or something like that often relatively complicated many of them have
been detected in marine sponges and animals like that and this is one of
them it’s called flubaroo sand b1 and he showed that you could take a molecule
here which had a double bond and a double bond join them together and make
a big ring and now that ring generates this carbon-carbon double bond and makes
ethylene ethylene is actually a natural product a gas that goes out of the
reaction and then you elaborate a little further and finally make that that not
fairly complicated molecule so this is that way he showed that you can do this
and this is now a way that is of interest to many people for making
pharmaceuticals and drugs for various Jesus and I’m still involved in in fact
trying to do that with the so called generation 3 catalysts so this is really
about 1996 at the end of the generation 1 catalysts of that motive denim and
tungsten type that I first mentioned the second generation catalysts that really
are the next 10 years or so kind of variations of the first generation
catalysts they have these two alkoxides joined together by a what’s called a by
dentate ligand two by phenolate or by nap so eight something having phenyl
rings in it joined together and these are like your right hand and left hand
they are chiral so this one has the S configuration as we call it and it is
what we say in anti-america pure it’s like you’re having it’s like a left
handed catalyst for example and held up my right hand but I meant left handed
catalyst and so what happens is you can you can make molecules that then
themselves contain carbons that have four different things bound to them and
they are themselves in a numerically pure one hand or nearly so and that’s
the way most carbons are many of them in your body and in nature in general
they’re not they’re not symmetric they are asymmetric and they are in fact
chiral and often in nature at least in a numerically pure one configuration about
that carbon so you can take simple compounds like this one and with the
seen ant America the pure catalyst five mole percent it means you can do the
reaction twenty times it’s of course the rather high percentage for a commercial
application but this just demonstrates that that you can do it and you can
upgrade these simple molecules to rather complicated molecules that in that have
one specific structure greater than 99% the structure that I show here in good
yield very cleanly and quickly so these were
catalysts explore between 97 and thousand seven and I should mention
before I move on that besides organic chemistry you can’t make
polymers from these metathesis capitalists because in strange rings
like this fancy molecule here this tricyclics species you could open up
these double bonds and link them together with double carbons and other
molecules and make polymers you can do that twice and so in this case you make
a very highly cross-linked we say cross-linked carbon polymer and this is
a very very tough material this is made now with a ruthenium base catalyst that
Bob Grubbs has made and studied in the last 15 years since about the mid 90s or
so so it goes under various names telling met on and so forth it’s a
highly cross-linked polymer that’s used for things like automobile fenders and
chemical reactors and so forth and molybdenum one one of the my polymers as
I call it will do the same sort of reaction making after hydrogenation of
the double bonds in the polymer that is made a very highly it’s apparently is
it’s a sensory plastic glass it’s a it has glass like properties but it’s an
organic material that you can put on surfaces dissolve it and or melt and put
on surfaces so this is an optical disc coating they use it for lenses and and
so forth that’s made by Matsui now using one of these well-defined catalysts of
molybdenum well-defined meaning we know what it is so initially these catalysts
these metathesis catalysts were were black boxes and that was really what
everybody was interested in finding out in starting in the 70s you know what was
in this box that did this wonderful reaction we can’t we can’t play with it
because we don’t know what it is so we can’t make variations of it and that’s
what Grubbs and I did grubs for ruthenium and me for
molybdenum and tungsten this is Bob groves his contribution one men of many
variations ruthenium is two groups to the right and the periodic table there a
table there’s the crucial metal carbon double bond it’s not as sensitive to air
and moisture because as you move to the right in the periodic table the metal
carbon bonds become less reactive in general less polar and so it will
tolerate air and water and that made it very very useful for organic chemists
who didn’t want to work in dry boxes or inert atmosphere boxes they wanted to
work out in the air more or less and they could do that with just maybe a
little bit of nitrogen over the to flush out the the flask but they could they
could prepare everything on the bench top and so huge advances advances were
made then using these ruthenium catalysts because they were relatively
insensitive to air and water but they are different they’re the same many of
the reactions are the same but in the end in the last few years we’ve so we’ve
shown that molybdenum and tungsten can really do some remarkable things so all
that led to the Nobel Prize then in 2005 I thought I’d tell you a little bit
about Nobel you know where where he came from you might not know he was a Swede
that’s no surprise he was born in 1833 it was a chemical engineer he was born
into a family of chemical engineers and in that period when he was active
starting around 1860 or so things were really heating up as the Industrial
Revolution him many of the civilized parts of the world and so a lot of
things were happening and so he died in 1896 and he wasn’t married and in his
will he left all have his money and I think it was at that time something like
13 million dollars which in 1896 was quite a bit of money to establish the
Nobel foundation and to give it all away in the form of prizes five prizes
physics chemistry medicine literature and peace and the way he made his money was to
really find a way to tame what we call nitroglycerin
so nitroglycerin this is glycerin that’s a natural product you replace these OAH
groups with Oh no2 those are really in oh three groups no.3 is nitrate it
usually explodes especially if you have a lot of them and that’s what Sobrero
had found in 1847 that you could nitrate a glycerin and make nitroglycerin and I
know for a fact that it works I didn’t make very much though I’ll tell you but
he learned it it’s unstable and it would it killed a lot of people that would
explode unpredictably and he found that if you mix the basic basically made a
paste of it with what’s called Kiesel goo or diatomaceous earth basically a
kind of lime skeleton in diatoms and the sea floor you could make a paste that
you could still set off with a blasting cap but it wasn’t unpredictably
explosive so this is called dynamite this comes from Dinah must agree –k
word for power so this was very important to blasting of rocks and
construction and so forth so he made a lot of money in this discovery and for
other discoveries he was he spent most of his time in st. Petersburg Russia and
he was sweet as I said but he was also fluent in Russian German and English and
of course Swedish so he was a businessman / scientist all of his life
he actually lost a brother in in an explosion he did a lot of work on a lot
of research on nitroglycerin itself and in one huge explosion he his brother was
killed along with several other workers so it took between 1896 6 and 1901 5
years to establish the Nobel Foundation and figure out who’s going to get the
prizes and he explained all this in a very long will of one-page I think it
was so I don’t they didn’t have much to go by so this was all new
but they did have 13.5 million dollars so that’s a good place to start so these
are the the five areas of the original Nobel Prizes there’s a sixth one now in
economics which actually isn’t the Nobel Prize it’s a prize from the Swedish bank
in honor of Alfred Nobel established in 1969 but it’s usually called the nobel
prize in economics economics didn’t exist in 1896 or around the turn of the
century so here are the first recipients William roentgen for x-rays vant Hoff
you might recognize any students in the audience physical chemist fund burying
and medicine and and so on very often Peace Prizes go to well the
Red Cross is now won three Peace Prizes so you can win more than one prize and
three individuals four individuals have won more than one prize but it’s very
uncommon so they’ve been about 800 total prizes now given out over the last 110
years going to be the this is the end of this year will be the 110th anniversary
of the first Nobel Prizes they weren’t given out in every year during the war
years there were obviously some problems I’m talking about World War two but
it’ll be 100 and 10th anniversary in 2011 so the Swedes do it the whole thing
so they discuss who they think should get a Nobel Prize and a lot of people
can nominate whoever they want for the Nobel Prize but it’s a it’s a
percolation process it takes a long time sometimes my case 30 years so it can
take I think the record short time is like eight years but usually between the
discovery and the prize it’s thirty years or more and what was I going to
say Oh mmm forgotten here’s something important interesting the interestingly
the records of these deliberations are public only after 51 years so I’ll be
long gone before anybody who know we can read about what happened in the
deliberations concerning me and Bob Grubbs and Eve Chauvin so up to three
recipients may receive the award in any you know it can be one-third one-third
one-third or one-half one-fourth one-fourth all of wars are irreversible
not negotiable one person has declined a Nobel Prize
that was jean-paul sartre he thought he was you know above Nobel Prizes so he
didn’t decided he wouldn’t take it they’re only given to live in living
persons there have been a couple of one incident I know of when they were
announced or between the time they were announced which is early October and the
ceremonies which is on the anniversary of Nobel’s death its December 10th you
know he passed away so he had the satisfaction of knowing he won a Nobel
Prize but he didn’t collect the money as heirs collected the money I mentioned
here four people have won two Nobel prizes Madame Curie Paul Sanger Linus
Pauling and I named John Bardeen in physics Sanger in Bardeen are the only
two who have won their Nobel prizes in the same area chemistry and physics so
here we are in 2005 the prize as always they have a quotation to go with it this
prize was for the development of the metathesis method in organic synthesis
so I’ve been talking about metathesis and I’ve talked about some organic
molecules and that’s what the prize was for I’m not an organic chemist I’m an
inorganic chemist like presidential over here so I got my prize in another area I
guess but I do something that is beneficial to another field like organic
chemistry Bob Grubbs is an organic chemist and Yves Chauvin as a polymer
chemistry was a polymer chemist he’s still alive but he’s retired now so you
really have to do something that’s a benefit to mankind and usually benefits
some other areas some other subject area although there are prizes that are
really kind of one-off type things and they don’t seem to have been
fitted anyone and there are prizes that are you know frankly probably mistakes
but these are all irreversible once it’s done it’s done
so here is a picture at the Nobel foundation there’s even one of the
recipients is not shown as Harold Pinter who got the Prize in Literature for I
used to play write was a playwright he was very ill at the time and has since
passed away so he couldn’t make it to the Nobel ceremonies here’s Bob groves
he’s a little bit taller but he has less hair than I do
and there I am this is my family my mother was alive at the time she was
92 and I asked my brother Ted I was here on the left I don’t know if you can see
that very well and he’s a physician or was a physician surgeon and I asked him
whether it was wise to take my mother to the Nobel ceremonies at age 92 and he
said wow she’s determined to go so that was it so she went so that’s Ted and his
wife and my brother Luther and his wife and me and my wife Nancy that you saw in
that early picture and of our marriage in 1971 and my mother in the front my
wife’s family’s a little bit bigger so she has a sister Francis and three
brothers Edwin David and Johnny here and their wives David is unmarried here here
are my two sons Andrew and Eric and this is Rebecca who is married to Andrew and
was married to Andrew at the time she’s a photographer an artist and you can she
see she’s the splashy assault us although all of them all of us will look
pretty good friendly at that at these ceremonies so that that’s what the
ceremony looks like in the Town Hall it’s a big big hall limited capacity so
you can’t bring everyone you want to bring I bring brought 18 people and paid
for their way and we had a lot of fun you can’t see it probably down here to
the right but I always like to point out that
one of these is my I think that’s my wife’s head and that’s my one of my sons
and that’s my other sons are there they’re in the second row and here we
are all lined up physics people three of us three of them first and then the
three of us to economics re to medicine and to economics people and then Harold
Pinter who who couldn’t be there this is the King Gustav and and his wife Silvia
the king and queen these are members of the Swedish academies who make these
decisions and these are other Nobel laureates who just happened to be in
town they want to come out and hang out on the stage and because you do get a
full orchestra and a woman with a wonderful voice is up here I mean she’s
really fabulous they sing between subjects physics and
chemistry it’s very nice but it is tense because you have to go out and you have
to suppose meanwhile you have to stand up and you have to go receive the prize
from the king and I’m told that about 225 million people watch this ceremony
live so it’s a little you know my heart was beating pretty rapidly at this point
so I didn’t know if I could do it or not but I did and I said stand up and so we
all stood up and then you have to go out and receive the prize from the king he
gives you the medal and a diploma and then he though sends you the check in
the mail or actually they don’t be transferred by you know between banks
these days so there’s there’s a diploma all hand illustrated and hand bound and
my wife is a bookbinder conservator so she really likes likes this hand on
diploma and there’s there’s the the metal 18 karat gold it’s worth a bit but
you know I keep it in a bank vault I don’t plan on melting it down so this is
one addition to my family now it was my youngest son’s fiancee was Annabelle
she’s now a postdoc at MIT and brain chemistry and Eric and she live in a
house they bought about a year ago this time on his birthday March 16th a couple
days ago a few days ago so that that’s how we looked on stage
after the ceremonies white tie and Tails all the men running around and white tie
and Tails for anything breakfast you name it going out there
and white tie and Tails and the women in beautiful gowns so it’s very nice and
then we have a little dinner for 1300 people and this is this is in that it
was in Symphony Hall was the ceremony this is the town hall and so these are
where everybody’s going to sit all the guests and these are where all the king
and queen and other laureates and dignitaries are going to sit and then
you walk down this this long staircase in order to fill up the central table
and in this year they started out with the tables kind of bare and then they
brought in flowers and a lot of singing between courses and beautiful acapella
singing and Sweden which I do very well a lovely event this is my wife walking
with Robin Warren who is one of the recipients and the medicine prize
you can’t walk with your spouse or partner you’re paired up by by someone
on the committee at some point to make sure that you’re not you know that
you’re you’re okay you’re not going to do anything crazy and then then they try
to pair you up with somebody who’s who’s appropriate and in my case that was
Vince’s Madeline so I hit the jackpot so this is the youngest of the three
children the princess Madeline was 22 at the time and a little too young for me
but you know it’s just she was definitely beautiful so it was good I
was worried about stepping on her gown there was just not being able to find
the next step so I was looking down all the time I shouldn’t have done that but
you can’t go back and replay these things and then this is of course now
filled with people I’m somewhere around here the king and queen in the middle
and people all up and down the table it’s a wonderful wonderful event few
photo ops at the end so these are the chemistry recipients here
if Chauvin lost his wife for about two years before the prize so he was
accompanied by his daughter and King Gustaf and Queen Silvia so one thing I’m
getting toward the end here but I wanted to mention that the Nobel Committee said
the metathesis method was green now green these days means ecologically not
ruinous that is aekta logically appropriate good for the good for nature
and non polluting their various things it can mean certainly it means
perhaps the starting materials of a renewable material not petroleum-based
you might use water as a solvent not organic solvents and the products might
replace petroleum products of course we’re not going to have petroleum
eventually and it’s non polluting perhaps and and so I could see how in
fact some aspects of what they called Green was was true of metathesis it’s
clean it’s efficient it’s fast and and you can make products now as we know
from renewable materials you can make chemicals from renewable materials like
seed oils using metathesis methods I thought I would mention just one of the
molecules that you know in a family of molecules that is made now by the
metathesis process of hundreds and and it’s a pheromone now a pheromone is as a
fairly simple molecule usually that’s given out given off by insects and other
animals in nature and some people think humans to attract one another so there’s
a pest called the peach tree borer it’s a pest in the larvae form and so of
course to make larvae female has to lay eggs and male female has to mate and the
male finds a female through the female giving off a little bit of this
pheromone and so the male swims upstream if you like and fine
the female and and and mates and these larvae produced and then they infest a
tree various almond and peach nectarine and other fruit trees and they ring the
tree and then the tree dies so it’s a big big problem in in that industry and
of course the old way to do it would be to just kill everything with DDT and we
know DDT’s band or some other insecticide but the smart way to do it
is to fool the male so the smart way to do it is to make the pheromone so the
pheromone of the peach tree borer actually looks like this
it or at least this is part of it it’s actually a mixture of this type of
molecule and something where you have instead of this this ester group at the
end it’s an alcohol that you can make the ester from it’s a 83 to 17 mixture
of these two but you make this one from two pieces that look like this the
left-hand piece taken twice in the right-hand piece taken twice and use a
metathesis catalyst to join this piece with that piece and you make then two of
these and so that’s this comes from petroleum this comes from vegetable oils
and this is a bonafide process that produces then this
pheromone or it actually duplicates an action natural pheromone and this is
then used in very small quantities so grams which is about the size of tip of
my little finger here one gram will cover an acre so you don’t have to put
you know kilograms of material out there because it’s very potent at least to the
the male peach tree borer fly who can smell it and at a very low level and so
he becomes very confused and can’t find a female so that’s it for mating season
nothing happens they die and it’s all over and the peach trees survive so
that’s a smart way to to really treat a pest problem I wanted to tell you just
to finish up I actually lied to you here I mentioned it earlier the
olefins carbon-carbon double bonds has to have two forms this is called the sis
form where the two whatever if there are two groups attached as they are here or
on the same side so this this is there to M protons here H’s and those two H’s
and these two carbons which are actually CH 2 s are bound or or lie in the same
plane so you can put these two groups on the same side of the double bond or you
can put one on one side and one on the other side this is called the SIS form
this is what’s found in nature and so for a long time up until about two years
ago even after the Nobel Prize which was given for this method we could not make
selectively the cysts form or all the z form nature
could do it and of course in small rings it had to be the SIS form couldn’t make
a transform but it would be nice to make the system because those are what are
present in natural products such as this pheromone and recently we’ve found out
how to do that so this just reiterates what I said it would be nice to be able
to make one of these the z form or the SIS form not the other this is one where
they’re both on the same side these are one groups whatever they might be and
this is one where in their own opposite sides this one is generally not found in
nature very much and it’s less desirable in organic chemistry but usually you
make about 80% of this one and 20% of this one so that’s not a very good yield
of the one you want so Z is the most valuable in general here I show some
natural products this is the this is an anti-tumor agent motive poor means see
there’s a cyst double bond there’s a cyst double bond and epithelial bond and
98% yield there’s something called civet tone which is a fragrance given off by
this civet cat the president’s and president and most perfumes a large
number of them at least and so sis double bonds are important
and this is now the generation 3 catalyst you see a lot of lot of things
here but you know in addition to the metal which happens
to be tungsten carbon double bond in the metal nitrogen double bond there was
another nitrogen-containing group and then an oxygen containing group there
are four different things on the metal that metal is therefore what we call
chiral just like a carbon with four different things on it is chiral this is
a chiral metal center and we’re finding that there are some very special things
about chiral metal centers and I’ll talk a lot about this tomorrow but one of the
things that we can do now is to very cleanly take these two olefins and join
them together to make the cysts olefin and ethylene a room temperature with
this catalyst greater than 99% of the product is this sis product the one that
normally you only get in about 20% yield and it’s a very high yield 90 percent or
so this is has come out in a journal we published in called organometallics a
couple days ago now on march 15 a few days ago I thought I would mention one
other thing and that’s what John alluded to the importance of fixing nitrogen
reducing it to ammonia it’s done by probably the most important process of
the 20th century the haber-bosch process both of whom got a nobel prize this was
the chemist this was the engineer in perfecting this brute force method of
making ammonia from molecular hydrogen and nitrogen of very high temperatures
and very high pressures it’s very expensive to build these plants and but
they run they make more than ten to the eight tons per year of ammonia this way
nature also does it you know about the same scale at room temperature and
pressure and we have found as John mentioned in 2003 that a way to do it
with molybdenum again molybdenum the answer to life the universe and
everything so it it was another achievement that I’m proud of probably
my second achievement it’s not going to win another Nobel Prize but I
got one that’s that’s fine I’m happy I want to just mention two things people
don’t do work don’t do research without money like everything else and these are
the three foundations that have helped me National Science Foundation National
Institutes of Health in the Department of Energy and a little bit of money from
the Army recently have helped me in basic research for carbine chemist
carbine compounds out cover Dean’s the application of them to organic chemistry
and collaboration with Amir ho Veda and for polymer chemistry called romp
ring-opening metathesis polymerisation I’ll talk much more about all these
projects tomorrow I want to finish with just noting what I noted earlier here’s
John Osborne and his wife Karen my wife Nancy in 1996 at a restaurant in laberge
de Lille from there Strasbourg and it was four years before John died of a
brain tumor so I I often look at this picture and wish that he were around to
enjoy what has happened to me but maybe he’s looking down on us who knows so
with that I want to thank you all again and hope you enjoyed it yeah if you want to stick around for a
few minutes I’d be happy to answer some questions I have one question I was
wondering if you had any clarification on that experiment that resulted in the
fire department coming over yeah so chemistry sets back when I was eight
years old had good things in them things like potassium nitrate charcoal sulfur
and you mix those up in the right proportion and you get something called
gunpowder which I did and it worked didn’t work very well it didn’t go boom
it wasn’t mixed up very well so kind of fizzled and some of it then hopped on to
a rug that was in the basement in my lab or near my lab and pretty soon the rug
was kind of fizzling and it got started to burn and so I had the the sense to
just gather it all up and throw it out the window
generated quite a bit of smoke in the house but nothing really was damaged
besides the rug which was not not a special rug so that’s some explanation
of what happened and when the fire department was called to my house I
think I was about 12 years old at the time 12 year olds do that sort of thing
you know now is your chance yeah
so the aunt question was don’t have any plans for my work in the future yeah
these new catalysts that I mentioned right at the end a really unique since
ruthenium the competition by the fellow called Grubbs doesn’t do these reactions
so we can do reactions that can’t be done by any other catalysts and so we
patent these things I recently started up a company back in December and I
don’t I don’t really care about making a lot of money I just want to I want
somebody to make what I’ve done useful and so I thought this was a
sensible thing to do I had the chance to do that so so I’ve done that so I don’t
work for the company I’m still doing research but I patent things then at MIT
then company licenses those patents and so on so that’s what I’m doing in the
future one of the things well okay so the question is do I want
to share with everybody the secrets that I know especially on developing
countries I try the best I can to do that I travel and give lectures but I
don’t have any great secrets I’m not I’m not you know I’m not a deity here you
know I’ve done I’m done I’ve done some good things and I explain you know what
I’ve done and try to give you some idea of what it takes to to do that but I
can’t I can’t give you a recipe for how you can do it or how any one person can
do it and I don’t know what special combination of talents I have it just
happens that I have some combination that this right combination so I can’t
really really give you the answer I try but I can’t give you the answer yeah so times I was discouraged in my
research well when the house was almost burning down I was trying to scourge we
all have times that were discouraged but one one thing one thing that it does
take to become successful is to not let that deter you in fact sometimes I think
scientists feel like they get stronger when when they meet some resistance and
sir they’re discouraged but they they go out and you know have some wine or
something the next day they’re fine you know they back in the lab and they’re
gonna go to fix the problem so I don’t I can’t think of any particular you know
gigantic discouragement that I had just a lot of little ones sure almost every
day discouraged in some way but usually it’s a fairly small thing and you can
you can work through it so I didn’t have any
any any big problem but a lot of them if you add them all up sure that’s what we
do we try to have her try to come back beat mother nature somehow but she’s
tough very tough any advice that I wish I had been given by a mentor well I was
given a lot of advice by John Osborne and my postdoctoral supervisor
Lord Lewis still and by George Marshall my group leader and George Marshall said
you should leave the pond he said he knew that I wasn’t going to be a lifer
at DuPont I guess that’s what he was saying he didn’t tell me to get out you
see he said you know maybe maybe you you really should go find an academic job so
that’s what I did so I’ve been thankful for all that advice I can’t I can’t say
there’s any advice that is not given to me that I wish I had had except maybe to
answer to life in the universe and everything but I learned that myself so
eventually we lived in him so Thompson is pretty good too and tantalum was my
first love so that’s I can’t they’re all nice but no I I can’t say there was any
specific advice that I wish I had been told so the answer is helmet how much time do
I spend in lab how do I divide it and what’s the longest time I’ve spent on
something right oh you mean one just a marathon in the lab well let me start
right now I don’t go in the lab I’m prevent it from going in the lab to do
anything because my students can’t stand it you know it’s just no I’m not I in
fact whenever I do something I do Google in the lab they all gather around they
think it’s really amazing that I can actually do something so but so I don’t
myself work in a lab anymore but I’m in the lab talking to them all the time long in my creative period I like to
think I’m so creative but you know when I was a graduate student I would work
long hours in fact my there you see my PhD supervisor would which kind of
opened the door and throw in a sandwich and closed a door because he knew I
needed some food you know because that that was the main problem I hadn’t eaten
for like 12 hours so no I I guess the longest period of time you have some
long days 1214 hours 16 hours I don’t know I never did all-nighters as I
recall except to study because you don’t want to do that if you’re in the lab
it’s not good because you do lose concentration and so forth and you have
accidents so that’s not good how do I divide my time well right now
it’s yeah it’s more complicated I don’t go in the lab as I said except to talk
to students but I spend as much time as I can talking to them when I’m there to
help them out I only have five students now about seven postdocs so I’m just no
longer taking students because that’s a five-year commitment if you take
students before you retire if you retire and so I’m doing what’s called switching
to postdocs so I don’t I don’t take students well I did
I have a family and you saw them and so I had to balance a lot of balls but it
is possible and all you young people out there I want you to know it’s possible
to balance all those balls it’s difficult from time to time but it can
be done okay so give it give it to me again what
what yeah that’s a good question you don’t have to start when you’re
eight I just so happened I did but some people won Nobel Prizes didn’t get
interested in their subject – they were like 27 you know they were in graduate
school the quite a number I mean I I can think of one or two but I think they’re
they’re quite a few so you don’t you don’t have to become interested in your
lifelong work when you’re young to actually be successful at it
very successful so yeah that’s the answer you can start late you can be a
late bloomer okay as we say yeah so what’s the goal now well I
showed you how to make Z double bonds that’s that’s nice we want to make
selectively e double bonds and then if you come to my talk tomorrow I’ll show
you show you how you can put those to use and and completely control the
double bond chemistry because making and manipulating double bonds in organic
chemistry believe it or not is in a relatively primitive state if you think
about it there’s some reactions that work but none of them selective and and
none of them catalytic really so there are double bonds everywhere you’re full
of double bonds believe it or not and so that’s it’s it’s going to continue I
don’t think any other metals and the ones we know about molybdenum and
tungsten and ruthenium are going to be successful for various reasons I could
go through the list but it’s true that people have tried other metals tantalum
that I tried in the beginning it’ll do this reaction but it’s very reluctant to
do the reaction other things happen in the catalyst decomposes so that’s
generally what you’re fighting these metal carbon double bonds are natural
products so you’ve got to remake them that’s the whole idea that becomes a
catalytic process you use it over and over and over and over again if it
decomposes at some point then that’s that’s it and that’s what happens for
virtually all other metals there are other reactions that set in and don’t
allow that we actually to proceed so that the future is more of what I’ve
just shown you and you can hear about tomorrow in great detail if you’d like you know it’s a good question though
where what was I doing making tantalum compounds metal type in single bonds
right I was just having fun you know I thought and that’s what Sciences often
do I mean they they they have a goal but they do things because they’re learning
it’s new they can publish papers and maybe they’ll make it as covering like I
did I was fortunate so yeah I had my reason for making metal carbon double
bonds tantalum carbon metal carbon single bonds tantalum carbon single
bonds and that was to make another polymerization catalyst but you know if
you knew you were going to make a discovery you could make lots of
discoveries because you could predict what you’re going to do but you can’t so
you have to be doing something else in the process and that was my my excuse I apologize for cutting this off it’s very
animated and very interesting to hear you people ask these questions however
first of all I would invite you to come to his seminar tomorrow which is at 410
in the lecture halls 1352 at 410 and he’ll tell you more about this and I’ll
also invite you to a an hour tomorrow afternoon from 115 to 215 in room 16 51
where professor schrock will be happy to talk with you and discuss career plans
research plans etc and if all of you come we’ll find an auditorium where we
can meet so now there are some refreshments over there at the table and
and professor stock will be here a few minutes yet and you might be able to
buttonhole him before he leaves I’m not going anywhere I’m here thank you very
much

Author Since: Mar 11, 2019

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